CAC Shop: Looking for unique, well-designed souvenirs? This store, run by the Chicago Architecture Center, should be your first stop. You'll find Frank Lloyd Wright bookmarks, puzzles of the Chicago skyline, picture frames with patterns designed by famed local architect Louis…
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Chicago Attractions
From the bustle of the Loop on a weekday morning to the tranquility of Lake Michigan on a cool fall afternoon, Chicago is an experience in contrasts. Its cultural offerings and historic attractions draw seasoned international travelers, but the city's mix of family-friendly museums, beautiful parks, and iconic skyscrapers also attract vacationers of all ages. The fun -- and the challenge -- is to fit everything in one trip. You can put together a full itinerary each day and still have plenty left over for your next visit.
What you see will depend on your interests and stamina. The city's museums alone could keep you busy for at least a week. (If you don't have that much time, the top three exhibits that shouldn't be missed are the Impressionist masterpieces at the Art Institute of Chicago; Sue, the biggest Tyrannosaurus rex fossil ever discovered, at the Field Museum of Natural History; and the U-505 submarine at the Museum of Science and Industry). Come summertime, a stroll through picturesque Lincoln Park Zoo on the Near North Side is the perfect way to spend an afternoon; the setting makes it worth visiting even if you don't have kids along. (Added bonus: It's free!)
From a traveler's perspective, visiting Chicago is especially hassle-free because the majority of the places you'll want to see are in or near downtown, making it easy to plan your day and get from place to place. And because this is a town with a thriving tourist economy, you have plenty of guided sightseeing options: walking tours of famous architecture, boat cruises on Lake Michigan, and even bus tours of notorious gangster sites. If you're lucky enough to visit when the weather's nice, you can join the locals at the parks and the beaches along Lake Michigan.
Extensive public transportation makes it simple to reach almost every tourist destination, but some of your best memories of Chicago may come from simply strolling along the sidewalks. Chicago's neighborhoods have their own distinct styles and looks, and you'll have a more memorable experience if you don't limit yourself solely to the prime tourist spots. And if you really want to talk about da Bears or da Cubs, chances are, you'll find someone who's more than happy to join in.
64 Results
- Observatory
360 Chicago (formerly Hancock Observatory)
875 N. Michigan (the former Hancock Center) may not be quite as famous as the Willis (née Sears) Tower, but it’s more central to the Loop and River North than its taller brethren. A high-speed elevator carries passengers to the observatory in 39 seconds, and on a clear day, you can… - Museum
Adler Planetarium
The stately, 12-sided building may be historic (it was the first planetarium in the Western Hemisphere), but thanks to cutting-edge technology, the attractions here will hold the attention of even the most jaded video game addict. Since 2011, the most technologically advanced digital… - Museum
American Writers Museum
What makes a voice uniquely American? How does literature shape history? Who knew that poet Ezra Pound was such a hottie?The first two are the two central questions tackled at Chicago’s American Writers Museum….and the third is an offhand discovery of the sort that will delight… - Sports Venue
Arlington International Racecourse
With its gleaming-white, palatial, six-story grandstand and lush gardens, this racecourse is one of the most beautiful showcases for thoroughbred horse racing in the world. Its storied history stretches back to 1927, and such equine stars as Citation, Secretariat, and Cigar have… - Art museum
Art Institute of Chicago
If you’re planning to visit the Art Institute of Chicago, I’ll give you fair warning that you may want to schedule a nap in your afternoon. With more than 300,000 works in its permanent collection, spanning 5,000 years of creativity, the gargantuan and seemingly ever-expanding campus… - Performing Arts Venue
Auditorium Theatre
A truly grand theater with historic landmark status, the Auditorium gives visitors a taste of late-19th-century Chicago opulence. Designed and built in 1889 by Louis Sullivan and Dankmar Adler, the 4,000-seat Auditorium was a wonder of the world: The heaviest (110,000 tons) and most… - Religious Site
Bahá’í House of Worship
Up the road from Evanston in Wilmette is the most visited of all the sights in the northern suburbs, the Bahá’í House of Worship, an ethereal edifice that seems not of this earth. The gleaming white stone temple, designed by the French-Canadian Louis Bourgeois and completed in 1953,… - Zoo
Brookfield Zoo
In contrast to the more modest Lincoln Park Zoo, Brookfield, located in the western suburbs, is enormous, spreading out over 216 acres and housing thousands of animals—camels, dolphins, giraffes, baboons, wolves, tigers, green sea turtles, Siberian tigers, snow leopards, and more—in… - Landmark
Cafe Brauer
This landmark 1900 building is not technically open to the public, aside from a seasonal patio restaurant on the ground floor. (The lovely second-floor Great Hall, flanked by two curving loggias, is one of the city's most popular wedding reception spots; if you stop by on a weekend,… - Tour
Chicago Architecture Center (CAC; formerly Chicago Architecture Foundation)
The intention of the Chicago Architecture Center’s shop and tour center, new in 2018, is to help everyone appreciate the city’s main claim to fame. Exhibits include a scale model of downtown Chicago; profiles of the people and buildings that shaped the city’s look; a display that… - Garden
Chicago Botanic Garden
Despite its name, the world-class Chicago Botanic Garden is actually 25 miles north of the city, in the suburb of Glencoe. But if you’re looking for an afternoon of serenity, it makes for a tranquil day trip. Made up of islands, lagoons, prairie, and forest, this 385-acre living… - Museum
Chicago Children’s Museum
I know I’ve already said this, but the Children’s Museum is the main reason to visit Navy Pier (that is huge praise!). It also happens to be the second-most visited kids’ museum in the country. The entire three-floor building is like a giant playground that also happens to be… - Cultural complex
Chicago Cultural Center
The Chicago Cultural Center was built in 1897 as the city’s public library, and there’s actually a funny story behind it. Following the Great Chicago Fire of 1871, a sympathetic Great Britain sent more than 8,000 books to the city to help rebuild its library. What our English… - Tour
Chicago Detours
This small, independently owned company knows what it’s doing and the result is creative, informative, and fun tours. That’s because the owner of the company worked for nearly a decade as a tour guide and guidebook researcher herself. I recently went on a tour called “Interior… - Museum
Chicago Fed Money Museum
Walking into the Money Museum feels a little like walking onto a game show set (or so I imagine). Hidden within the stately Federal Reserve Bank of Chicago, here you’ll see lots of flashy exhibits brimming with dollar signs, an interactive display that lets you design your own money,… - Museum
Chicago History Museum
What do the atomic bomb, birth control pill, and Lincoln Logs have in common? They were developed in Chicago, which you’ll learn about when you visit here. The museum’s name is far more straightforward and boring than what’s within, so if you’re not a history buff, don’t let it scare… - Tour
Chicago Line Cruises
This company runs a 90-minute tour of architecture along the Chicago River, as well as specialty cruises like the St. Patrick's Day river-dyeing tour and live jazz cruises. The atmosphere is more upscale-educational than party-hearty, with knowledgeable guides who make no attempt to… - Attraction
Chicago Public Library/Harold Washington Library Center
A hulking building that looks like an Italian Renaissance fortress, Chicago’s main public library is the largest in the world, and even has its own El stop. Named for the city’s first and only African-American mayor, who died of a heart attack in 1987 at the beginning of his second… - Cultural complex
City Gallery
Along with the pumping station across the street, the Chicago Water Tower is one of only a handful of buildings to survive the Great Chicago Fire of 1871. It has long been a revered symbol of the city’s resilience and fortitude, although today the building is dwarfed by the high-rise… - Historic Site
Driehaus Museum
It’s like the Gilded Age never quite left the Driehaus Museum, and that’s just how owner and investment manager Richard Driehaus likes it. Driehaus, an art collector and philanthropist, whose Driehaus Capital Management firm is cattycorner from the museum, “discovered” this home in… - Museum
DuSable Museum of African American History
One of the first thoughts I had while reading the displays in this museum, was, “Wow, it’s nice to be reading the version of history that wasn’t written by old white men.” More specifically, I was reading a blurb on the Revolutionary War that focused on African Americans, rather than… - The Performing Arts
ETA Creative Arts Foundation
Since 1971, this theater has been staging original or seldom-seen dramatic works by African-American writers from Chicago and beyond. Along with Black Ensemble Theater (which performs at the Uptown Center Hull House, 4520 N. Beacon St.; tel. 773/769-4451;… - Museum
Ernest Hemingway Birthplace Museum
Ernest Hemingway was born in Oak Park, but judging from the museum dedicated to him, it seems that the city may have had a greater affinity with him than he with it. When you think of Hemingway, after all, Key West, Paris, and Cuba come to mind. But the Village of Oak Park, Illinois?… - Museum
Field Museum of Natural History
The Art Institute gets a lot of love when it comes to Chicago Museums, but I’ve always had a soft spot for the Field Museum of Natural History. The museum, which was named for one of Chicago’s most famous early residents and the museum’s first major donor, Marshall Field, is one of… - Historic Site
Fine Arts Building
A worthwhile brief stop for architecture and history buffs, this 1885 building was originally a showroom for Studebaker carriages. In 1917 it became an arts center, with offices, shops, two theaters, and studios for musicians, artists, and writers. Its upper stories sheltered a… - Historic Site
Frank Lloyd Wright Home and Studio
For the first 20 years of Wright’s career, this remarkable complex served first and foremost as the sanctuary where he designed and executed more than 130 of 430 completed buildings. The home began as a simple shingled cottage that the 22-year-old Wright built for his bride in 1889,… - Historic Site
Frederick C. Robie House
For architectural history hounds, Robie House is a must-see. Frank Lloyd Wright designed this 20th-century American architectural masterpiece for Frederick Robie, a bicycle and motorcycle manufacturer. The home, which was completed in 1909, is a classic example of Wright’s Prairie… - Tour
Gray Line
Part of a worldwide bus tour company, Gray Line Chicago offers professional tours in well-appointed buses. Excursions run 2 to 5 hours and feature highlights of downtown or various neighborhoods. For an additional fee, some tours include a cruise on Lake Michigan or a visit to 360… - Historic Site
Historic Pullman
Railway magnate George Pullman may have been a fabulously wealthy industrialist, but he fancied himself more enlightened than his 19th-century peers. So when it came time to build a new headquarters for his Pullman Palace Car Company, he dreamed of something more than the standard… - Museum
Hull-House Museum
Jane Addams was the daughter of a wealthy miller, who leased a mansion on Chicago’s poor west side in 1889, welcoming the area’s residents, many of whom were poor immigrants, into the home, called the Hull-House. Today, that mansion is a museum that highlights the accomplishments of… - Museum
International Museum of Surgical Science
Although it’s not quite as macabre as Philadelphia’s Mütter Museum, the International Museum of Surgical Science will be of interest to those with an appreciation for the weird, as well as surgeons and others in the medical field. Tucked into a 1917 Gold Coast mansion—the last… - Museum
Intuit: The Center for Intuitive and Outsider Art
It sounds like an X-Files kind of name, and, true, the art can get a little weird here, but you have no alien abductions to fear in this warehouse district gallery. “Outsider art” is a term attached to a group of unknown, unconventional artists who do their work without any formal… - Aquarium
John G. Shedd Aquarium
The Shedd is one of the world’s largest indoor aquariums and houses thousands of river, lake, and sea denizens in standard aquarium tanks and elaborate new habitats within its octagon-shaped marble building. Truly, the only problem with the Shedd is its relatively steep admission… - Park/Garden
Lincoln Park Conservatory
Just beyond the Lincoln Park Zoo’s northeast border is a lovely botanical garden housed in a soaring glass-domed structure. Inside are four great halls filled with thousands of plants. If you’re visiting Chicago in the wintertime, this lush haven of greenery provides a welcome… - Zoo
Lincoln Park Pritzker Children’s Zoo & Farm-in-the-Zoo
After hours of looking at animals from afar in the rest of Lincoln Park Zoo, kids can come here to get up close and personal. Unlike many other children’s zoos, there are no baby animals at the Pritzker Family Children’s Zoo; instead, the outdoor habitats feature wildlife of the… - Zoo
Lincoln Park Zoo
One of the city’s treasures, this family-friendly attraction is not only open every day of the year, but it’s also free. Even if you don’t have time for a complete tour of the various habitats—there are 49 acres, after all—it’s worth at least a quick stop during a stroll through… - Museum
Loyola University Museum of Art
Tucked away in the downtown Loyola University campus, right next door to Bottega Veneta, oddly enough, is the Loyola University Museum of Art. Although the museum’s website describes it as “dedicated to the exploration of the spiritual in art,” its revolving exhibits aren’t… - Museum
McCormick Bridgehouse & Chicago River Museum
This small museum tells the water-rich history of Chicago, which today has more moveable bridges than any city. The rapid growth of Chicago wouldn’t have been possible without its position on the river, where boats could haul goods in and out on a regular basis, solidifying the… - Park
Millennium Park
The northwest corner of Grant Park is the site of Millennium Park, one of the city’s grandest public works projects. Who cares that the park cost hundreds of millions more than it was supposed to, or the fact that it finally opened a full 4 years after the actual millennium? It’s a… - Natural Attraction
Morton Arboretum
This suburban oasis, located in Lisle, about 27 miles west of the Loop, covers almost 2,000 acres and is dedicated to preserving an amazing variety of trees and shrubs. You can follow walking trails through solemn forests, explore a re-creation of an original Illinois prairie, or… - The Performing Arts
Muntu Dance Theatre of Chicago
The tribal costumes, drumming, and energetic moves of this widely touring group, which focuses on both traditional and contemporary African and African-American dance, are always a hit with audiences. The company performs throughout the area at local libraries and community events,… - Museum
Museum of Contemporary Art
The MCA scored a major art coup by booking the David Bowie exhibition back in 2014–2015. It was the only museum in America to land the exhibit, which sold out handily when it was in London, and that speaks well to the art muscle of Chicago’s contemporary museum—one of the nation’s… - Museum
Museum of Contemporary Photography
This approachable, three-floor photography museum brings in cutting-edge exhibits from local, national, and international artists, thanks to its connection, literally and figuratively, to Chicago’s Columbia College—not to be confused with New York’s Columbia University—a small arts… - Museum
Museum of Science and Industry
If Disney were to make a purely educational theme park, it probably wouldn’t be too far off from the this humongous museum—the largest science museum in the Western Hemisphere—where exploring, playing, squealing, and climbing isn’t just encouraged, it’s practically required. Here,… - Tour
Mystic Blue Cruises
A more casual alternative to fancy dinner cruises, this is promoted as more of a "fun" ship (that means DJs at night, although you'll have to put up with some kind of "live entertainment" no matter when you sail). Daily lunch and dinner excursions are available, as are midnight… - Museum
National Museum of Mexican Art
Exploring the Latino-heavy Pilsen neighborhood is a bit like stepping into a different city, where the smell of spicy meats and soft corn tortillas fills the air, emanating from the many tempting taquerias. One of the cultural highlights here is the National Museum of Mexican Art,… - Museum
National Veterans Art Museum
A stroll through this intense museum is akin to peering into a soldier’s soul. Although it’s not exactly comfortable, it opens our eyes to the ways that war can affect soldiers, right down to their synapses. The works here, from sculpture to photography to portraits and more, were… - Attraction
Navy Pier
Built during World War I, this 3,000-foot-long pier served as a Navy training center for pilots during World War II. The military aura is long gone, and Navy Pier now thrives as a major tourist attraction, drawing more than 8 million visitors a year to the carnival rides, large food… - Library
Newberry Library
The Newberry Library, housed in a stately five-story granite building, is a bibliophile’s dream. Established in 1887, thanks to a bequest by Chicago merchant and financier Walter Loomis Newberry, the noncirculating research library contains many rare books and manuscripts (such as… - Museum
Oriental Institute Museum
They had me at the Egyptian mummy. Two of them, in fact, are on display here, one in a coffin, the other enshrouded in linen. The mummies, and all of the artifacts, statues, palace corridors, jewels, and other Near Eastern art items are here because they were unearthed in excavations… - Museum
Peggy Notebaert Nature Museum
I love that the third largest city in the U.S. is home to a nature museum. And it’s not tucked away in the 'burbs, either: Peggy Notebaert is on prime Lincoln Park property, across from the zoo, Lincoln Park, Lake Michigan and surrounded by plenty of, well, nature. One of the… - Religious Site
Rockefeller Memorial Chapel
To call the Rockefeller Memorial Chapel a chapel is false modesty, even for a Rockefeller. When the university first opened its doors, the students sang the following ditty: John D. Rockefeller, wonderful man is he Gives all his spare change to the U of C. John D. was a generous… - Tour
Shoreline Sightseeing
Shoreline launches 30-minute lake cruises every half-hour from its two dock locations at the Shedd Aquarium and Navy Pier. Shoreline has also gotten in on the popularity of architecture river tours. Narrated by architectural guides, they cost more than regular tours. A water taxi… - Theme Park
Six Flags Great America
One of the Midwest’s biggest theme and amusement parks, Six Flags is midway between Chicago and Milwaukee on I-94 in Gurnee, Illinois. The park has more than 100 rides and attractions and is a favorite of roller coaster devotees. The wooden daredevil coaster, Goliath, is a major… - Cultural complex
Spertus Institute for Jewish Learning and Leadership
Although this educational center collects and preserves an array of historic Jewish ceremonial objects, textiles, and sculptures, I have to say I was most excited to come here for the architecture and the view. The stunning modern building, which resembles a chunky, enlarged prism,… - Tour
Tall Ship Windy
One of the more breathtaking scenes on the lake is this tall ship approaching the docks at Navy Pier. The 148-foot four-masted schooner sets sail for 90-minute cruises two to five times a day, both day and evening. (Because the boats are sometimes booked by groups, the schedule… - Historic Site
The Rookery
From the outside, this gloomy building gives no hint of the beauty within. Designed by master architect Daniel Burnham in the 1880s, it was one of Chicago’s largest and most expensive office buildings when it was completed. (The name was a carryover from the old City Hall that… - Museum
The Smart Museum of Art
Small and plain on the outside, but incredibly scrappy within, this University of Chicago museum has an impressive array of items that span 5,000 years of humanity. That’s the same as the Art Institute, if you’re keeping score. The permanent collection draws from four categories:… - Tour
The Spirit of Chicago
This luxury yacht offers a variety of wining-and-dining harbor cruises, from a lunch buffet to fireworks cruises. This can be a fairly pricey night out if you go for the dinner package. - The Performing Arts
Theater Wit
Befitting its name, this troupe specializes in lighthearted productions filled with clever banter. But true to its motto, "Smart Art," Theater Wit also challenges audiences to think while being entertained. While it started as a vagabond company that performed in various venues… - Religious Site
Unity Temple
After a fire destroyed its church around 1900, a Unitarian Universalist congregation asked one of its members, Frank Lloyd Wright, to design an affordable replacement. Using poured concrete with metal reinforcements—a necessity due to a small $40,000 budget—Wright created a building… - Tour
Untouchable Tours
The days of Al Capone are long gone, but Chicago’s notorious past is still good for business, it seems, given the popularity of these “Gangster Tours.” The 2-hour bus trip takes you to all of the city’s old hoodlum hangouts from the Prohibition era, including O’Bannion’s flower shop… - Tour
Wendella Tours & Cruises
Started in 1935, Wendella is the granddaddy of Chicago sightseeing operators (it's now run by the original owner's grandsons). The company operates a 1-hour tour along the Chicago River and a 1 1/2-hour tour along the river and out onto Lake Michigan. (One of the most dramatic events… - Landmark
Willis Tower Skydeck
Before the Ledge opened at the Skydeck at Willis Tower (formerly Sears Tower) a few years ago, people were faced with a difficult choice for the best views: Willis or Hancock? Now, there’s really no competition. It takes a slightly wobbly 60-second elevator ride to get to the…
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Chicago Shopping
Near North's Michigan Avenue, with its designer shops and interesting stores like Crate & Barrel are a shopper's and people-watcher's paradise. A trip Downtown is not complete without a visit to Marshall Field's, now Macy's department store. Lincoln Park is the place for kitschy consumerism like at The Second Child and bargains at Lori's Designer Shoes. River North has antiques and art. Store hours are usually Mon-Sat 10am-7pm and Sun 11am-6pm.
47 Results
- Bookstores
Abraham Lincoln Book Shop
If you’re hungry for Abraham Lincoln lore, you’ll find a veritable museum at this antique reading room, which is filled with memorabilia and, of course, books, from rare and out-of-print editions to new. - Fashion
Alcala’s
Here’s a fun little Chicago surprise: a store dedicated to Western wear, and lots of it. While the surrounding Ukrainian Village has changed over the years, Alcala’s hasn’t, and thank goodness for that: The vintage horse statues out front are a hoot. Choose from thousands of boots,… - Fashion
AllSaints
Inside, industrial chunks of heavy, scary metal abound. Leather, zippers, and chunky spikey jewelry seem to dominate. But get past that, and the U.K.-based store reveals an edgy collection of fashion basics for men and women, mostly in grey and black, along with a small section of… - Toys
American Girl Place
If the giggles seem to hit a crescendo near Water Tower Place, this is why. Unless you’re a parent of a young girl (and really, even then) don’t expect to understand the excitement that builds around this pink palace, where dolls can visit the salon, photo studio, doll hospital, or… American Science and Surplus
Need a giant cloth frog splayed out, dissection-style, on your wall? Head to this huge science-centric surplus store that moonlights as a fun shop and lab depot. Here, science experiment kits and lasers may fill one aisle, while furry robotic hamsters, inflatable rubber chickens, and…- Housewares & Furniture
Andersonville Galleria
If malls were small, navigable, friendly, and consisted of handmade items from local artists and artisans, they’d be like Andersonville’s Galleria. It’s about a 30-minute train ride from downtown to see the 90+ tiny shops/stalls of art, clothes, gourmet food, gifts, jewelry,… - Electronics
Apple Store
It’s as though Apple constructed a giant magnet to lure passersby into this perennially busy store. Apple Store now takes online appointments, so plan ahead, and the shop should have you and your iProduct in and out in a jiffy. You can also hop the train to the Lincoln Park location,… - Fashion
Balani
Balani is the choose-your-own-adventure shop of menswear. Here, the clothiers (yes, clothiers) will consult with you on what you’re looking for in a suit and let you select the fabrics (wool, cotton, silk, cashmere), patterns, and colors, right down to the buttonhole. After you’re… - Bookstores
Barnes & Noble
This national chain ensures easy access to hundreds of thousands of books at its two-story Gold Coast outfit, and also hosts story time for kids, author signings, and other events. Another location is at 1441 W. Webster Avenue, at Clybourn Avenue, in Lincoln Park (tel. 773/871-3610). Bloomingdale’s
There are two options for Bloomingdale’s in the downtown area: Bloomingdale’s Medinah Home Store and Bloomingdale’s. The home store is located in River North in what was once a temple for the Shriners, an intriguing Moorish building topped with an onion dome, with dark brown bricks…- Gifts
Chicago Architecture Center (formerly Chicago Architecture Foundation)
I dare you to try to get out of the best gift shop in the city without getting out a) your wallet or b) your phone to take a photo of something you’re barely resisting buying, like a ninja samurai sword umbrella or a Frank Lloyd Wright Millard House votive candle holder. I've… - Food
Chicago French Market
Conveniently located within the Metra commuter train station, this darling, European-style market is filled with nearly three dozen stalls serving grab-and-go meals, like poke bowls and lobster rolls, to bakeries creating addictive mini doughnuts and brightly colored French… - Music
Dusty Groove America
In 1996, using a rickety old PC, Rick Wojcik and John Schauer founded an online record store at www.dustygroove.com. Since then, the operation has expanded in both cyberspace and the real world. Dusty Groove covers a lot of ground, selling soul, funk, jazz, Brazilian, lounge, Latin,… - Food
Eataly
I am absolutely in love with this Italian grocer, as is every guest I bring here for an afternoon. In addition to an incredible stockade of specialty foods imported from Italy (which include truffles in any form you can imagine), Eataly, located in River North, has a… - Food
Gene’s Sausage Shop & Delicatessen
If you find yourself in the Lincoln Square neighborhood with a hankering for sausage, Gene’s has you covered. This window-lined, two-level, family-owned shop employs European-trained sausage-makers to create more than 40 types of sausage. Check out the delicatessen, with its Eastern… - Fashion
Hazel
Whether you’re looking for a Mad Men–style dress, a pair of jeans, or an ironic Jesus t-shirt, Hazel has it. This affordable Ravenswood clothing boutique, just north of Lakeview, carries both men’s and women’s lines, and is run by a fashionable staff that is always happy to help you… Heritage Bicycles
On my first visit, I immediately fell in love with Heritage Bicycles, a coffee shop/bicycle maker/bike repair shop/bike apparel store in Lakeview. I still get that same warm and fuzzy feeling whenever I come back. First, the staff is so friendly, I can’t imagine them existing outside…- Wine
House of Glunz
Chicago’s oldest wine shop carries an inventory of some 1,500 wines, some of which date back to 1811. Ask the knowledgeable owners to steer you to the right bottle for your budget. - Fashion
Ikram
If you’re not a fashionista, you may wonder, when stepping into the very red Ikram building, if you’ll be allowed to leave in the dowdy duds in which you entered. That’s because you’ve just penetrated a hallowed Vogue-style space in River North, filled with couture du jour, thanks to… - Fashion
John Fluevog
Blend a little bit of funky, a little bit of sexy, and a whole lot of comfort, and you’ve got a pair of shoes by John Fluevog. One of just a handful of its kind of shops in the U.S., Fluevog feels like an especially good fit in Wicker Park, which is a similar mix of… - Toys
LEGO Store
This Water Tower Place shop is a brick-loving kid’s dream. Build your own mini figures and cities, and then choose individual bricks from the “pick and build” wall. Even adults will find something to love here, including architecture kits of iconic edifices. Plan to spend some time… Macy’s
The sign outside says Marshall Field and Company, because this was the former flagship of Field’s, which originated in Chicago, before a buyout that forced a name change in 2006. Aside from being the most ornate and historic department store in Chicago, at Macy’s you’ll find all of…- Beauty
Merz Apothecary
Tinctures, salves, ointments: They’re all here, at this old-timey beauty shop. A pharmacist opened Merz in 1875, selling herbal medicines and treatments that would, today, be classified as “alternative.” The shelves are stocked with all-natural soaps, lotions, perfumes, creams, balms… - Electronics
Micro Center
Friends stare at me blankly when I proclaim, time and again, “I love Micro Center.” This place has just about everything that has anything to do with electronics: computer and even Mac spare parts, software, toys, stylish computer bags, “As Seen on TV” gadgets, and even a grumpy… - Beauty
Mojo Spa
If you were to glance too quickly around this small Wicker Park store/spa, you might think you were in a bakery. That’s because many of the soaps look like delectable cupcakes, layer cakes, and bundt cakes. The store’s owner, a personal chef, created many of these items herself,… - Souvenirs
Museum of Contemporary Art Gift Shop
I must admit, in my visits to the MCA, that I often feel like I'm missing something, or that the art is over my head. At the gift shop, however, I feel right at home. The shop is small but loaded with clever little finds, like blinking jewelry, a book that pops up with 3D floral… - Souvenirs
Museum of Science and Industry Gift Shop
If FAO Schwartz invented a nerd toy shop, this would be it. Some of the gifts here are exhibit-centric, while others are just plain fun, like the spy handbook, pet tornado, and mugs/shirts/magnets with periodic table humor. With all the focus on science, technology, engineering and… - Bookstores
Myopic Books
This used bookstore is one of Chicago’s largest, and packs in as many tomes as it can, from the floor to the ceiling (well, almost) of three floors, with more than 80,000 books. You’ll find everything from new bestsellers to obscure, yellowed relics. The staff is usually chatty and… Neiman Marcus
Attentiveness is an understatement here. In fact, it’s not unusual for three different women to try and “sample” you with cosmetics and perfume as you leap on the escalator from the first floor. Those greetings continue to the second and third levels—also women-centric, with clothes,…Nordstrom
Located in The Shops at North Bridge, you won’t find the stunning architecture here that you see at Macy’s on State and Bloomingdale’s Medinah Home Store. Instead, the city’s only Nordstrom feels like a mall, albeit a refined one. Escalators lead to four floors of fashion. A small…- Food
Old Town Oil
Shoppers sip oil and vinegar as though they’re at a wine tasting at this tiny specialty store in Old Town. The friendly staff will greet you at the door and lead you over to the oil dispensers, and then share with you a pretty fascinating lesson on what distinguishes one olive oil… - Bookstores
Powell’s Bookstore
No, it’s not as big as the Powell’s in Portland (nor are the two related), but Chicago’s own little used bookstore is packed to the gills with titles. - Music
Reckless Records
John Cusack fans won’t have much luck finding Championship Vinyl, the record store from High Fidelity, because the store never actually existed. But just a few storefronts away from the Wicker Park location of Championship is a hipster-filled find called Reckless Records, where vinyl… - Housewares & Furniture
Restoration Hardware
This RH store sits within a gorgeous, 19th-century building that was once an arts school for women. Shoppers can wander the six floors, sit in the posh rooms and behold a glorious rooftop, complete with foliage (I bring guests here to take a peek and have a sit), all while imagining… - Fashion
Robin Richman
This sophisticated Bucktown boutique specializes in dresses, tops, and skirts that are a little bit flowy with just enough edge, thanks to the owner, who is a knitter with quite a unique sense of style herself. Robin Richman is frequently at the store, and she’s incredibly welcoming… - Housewares & Furniture
Rotofugi
It’s hard to call Rotofugi a toy store, because, really, the toys are figurines that double as art, and the store feels more like a museum gift shop, except there’s no museum in sight. This Lincoln Park/Lakeview store brings in artworks and toy creations from Eastern and Western… - Beauty
Ruby Room
The fresh, floral scent is immediately soothing, and the ladies who work here are smiley and helpful. This one-stop-beauty shop offers a little bit of everything, from the usual—scrubs, balms, and lotions, along with a spa and salon—to the woo-woo—energy healing, colon hydrotherapy,… Saks Fifth Avenue
I tend to get a little nervous when I enter Saks. Am I stylish enough to get their attention, or will I feel snubbed? So far, so good, at least at Chicago’s Magnificent Mile outpost. Despite the luxury appeal of the store, in my experience, the sales associates are actually quite…- Bookstores
Seminary Co-op Bookstore
Not everyone can nab the SAT scores required to get accepted into the prestigious University of Chicago, but that won’t stop you from visiting the campus bookstore. Warning: It’s maze-like, and you might wish for a GPS to get through it, but you may rub elbows with one of U of C’s… - Flea Markets
Shangri-La Vintage
When I had to stock up on '70s-style cruise wear for a New Year’s Eve Poseidon Adventure party, I came here and left fully styled. With the concentration of bellbottoms and butterfly collars at Shangri-La, you’d think you’d just walked onto the set of The Brady Bunch. This tiny… - Bookstores
The Book Cellar
A visit to the book cellar is as cozy as having tea with an old friend. Small but remarkably stocked, the shelves are lined with illustrative hand-written recommendations by staff, and a significant portion of the inventory is dedicated to Chicago authors. The little cafe is a great… - Food
The Spice House
I sure never knew how tempting a spice shop could be until I saw—and smelled—The Spice House in Old Town. Gift/souvenir alert: Here, spice mixes are named after different Chicago neighborhoods, like Pilsen Latino Seasoning, Back of the Yards Garlic Pepper Butcher’s Rub, and Ukrainian… - Fashion
The T-Shirt Deli
T-shirts hang in the windows like ham and salami and fill butcher display cases at the irresistibly shticky T-Shirt Deli. Shirts here are displayed like meat, and, if purchased, wrapped in butcher paper and served with a bag of chips. Your job is to come up with the perfect fashion… - Flea Markets
Vintage Underground
When a store has an entire category dedicated to “ocean liner memorabilia,” you know you’ve swum into vintage waters. Here, you’ll find the gloves, jewels, hats, and furs that call to mind Hollywood stars of years gone by. Wicker Park Secret Agent Supply Co.
This “undercover secret agent spy store" does, indeed, have a rack of ex-agent’s former trench coats, which sell for $20 each. But mostly, this eccentric little shop has trinkets, t-shirts, and books, a fair number of which are by Dave Eggers, who co-founded the organization. You…- Housewares & Furniture
Wolfbait & B-girls
Local is the theme at this trendy Logan Square gift boutique, where the wares come from 150-plus local designers, artists, and seamstresses. From flirty dresses, Chicago-centric t-shirts, Intelligentsia coffee, and artsy mobiles to locally made, non-toxic deodorant, this spot is as… - Bookstores
Women & Children First
The name is a little hokey, but don’t let that stop you from visiting this charming Andersonville bookstore. The mid-sized, feminist shop stocks more than 30,000 titles by women (along with titles by men), a colorful kids’ section, and is well known for its impressive selection of…
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Chicago Nightlife
River North rocks with Sound-Bar and Excalibur while many stylish saloons like The Signature Lounge are located Near North and Downtown. Blues and jazz haunts are scattered throughout the city as are sports bars and funky establishments like The California Clipper. Find a bit of everything in Lincoln Park - B.L.U.E.S., Goose Island Brewery and Webster's Wine Bar. Opening hours vary. Some bars open as early as 10am while dance clubs close as late as 4am.
96 Results
- Bar
10Pin Bowling Lounge
A modern interpretation of the classic bowling alley, this lounge is tucked away behind the Marina Towers complex. There’s a full menu of cocktails, craft beer, and gastropub snacks, served lane-side or in two lounges. Low lighting and giant video screens overlooking the 24 bowling…River North
- Bar
Ace Bounce
Imagine loud music, a trendy craft cocktail bar in an industrial-ish setting, and, well, balls flying everywhere (expect to get pelted!) and you’ve got Ace Bounce, a quirky ping-pong bar relatively new to the Chicago nightlife scene. Staff are on standby to walk you through the…The Loop Andy’s Jazz Club and Restaurant
The windows are aglow with neon signs advertising “live music” at this little brick storefront in River North. Its location, close to The Loop, is a draw for tourists, but you’ll find plenty of jazz-loving locals here, too—including, often times, those on the stage, who play two sets…- Bar
Apogee
It’s quite the scene on the rooftop of the Dana Hotel, with indoor/outdoor access, twinkling city views, and an alluring firepit. But it’s not just about the eye candy here. The drinks are on point. Each beverage is served in dreamy drinkware (it may resemble a mushroom or coconut)…River North B.L.U.E.S.
Located just a few steps from always-rocking Kingston Mines, this tiny spot is a bit more mellow and neighborhoody, since it lacks the national reputation and tourist draw. Because it’s so teeny, you can get eye to eye with the performers—and packed like sardines with audience…- Bars & Pubs
Benchmark
Technically, Benchmark is a sports bar, so it’s popular with the bros (read: former frat boys turned adult), and has more flatscreens than I care to count. But there’s also a see-and-be-seen quality to the space, and at night, the heels go on and everyone from college kids to cougars… - Gay & Lesbian Bars
Berlin
Get your freak on at Berlin, a favorite dance spot among all clubgoers, gay or straight. With a history of 3 decades, there’s a decidedly retro sense to Berlin, with Depeche Mode/New Order Nights and Björk Showcases on the calendar. In true gay bar fashion, almost every night has… - Gay & Lesbian Bars
Big Chicks
Men and women tired of the fashion-show vibe of Boystown head to Big Chicks, a casual Uptown bar with funky decor, including the lady-filled art collection of owner Michelle Fire, aka the original Big Chick. Regulars include a smart, artsy crowd of gays, lesbians, and heteros who… - Bars & Pubs
Big Star
This hipster honky tonk is known for whiskey, beer, tequila, and tacos. Lest you think that the booze begets the food ordering, the reverse is more often true. The chef-driven tacos, like the Taco de Panza with crispy pork belly, are the real siren’s song. While I prefer this… - Bars & Pubs
Billy Goat Tavern
You may know if from the “cheezborger” Saturday Night Live skit, but regulars at the original subterranean location are more likely to stop in for a beer and camaraderie first, and then opt for the mediocre cheezborger (“no fries—cheeps!”) to soak up the suds. Billy Goat remains a…The Loop - Bars & Pubs
Billy Sunday
You’ll need a dictionary to understand the drink menu, but don’t let that stop you from ordering one of the house-made tonics, which are full of booze, pumped with carbonation, and served on tap at Billy Sunday, a speakeasy-style bar named for teetotaling evangelist Billy Sunday. Or… Blue Chicago
Because of its location in River North, Blue Chicago has a big tourist draw, but holds its own with the locals too. What really distinguishes this club is its dedication to promoting the women of the blues, and man, can they sing. Talent is booked nightly, and the intimate club…Blue Man Group
The Briar Street Theatre has been the "Blue Man Theater" since the fall of 1997. The avant-garde New York City performance phenomenon known as Blue Man Group has transformed the 625-seat theater, beginning with the lobby, which is now a jumble of tubes, wires, and things…Buddy Guy’s Legends
If Chicago is the body and soul of blues music, then this club—owned and operated by rock-'n'-roll Hall of Famer Buddy Guy—is its heart. The best time to come here is in January, when Buddy himself performs, and has been known to draw in other famous musicians. That, of course, is…- Bars & Pubs
Carol’s Pub
This weird little Uptown honkytonk, just north of Wrigleyville, appeals to the young and hip, the old and broken-hipped, and everyone in between who can take a little grit with their MGD. A classic roadhouse, Carol’s comes to life on weekends, when live bands take the stage crooning… - Opera
Chicago Opera Theater
The "other" opera company in town, Chicago Opera Theater, doesn't get all the big names, but it offers an alternative to the more traditional Lyric by focusing on often-neglected or new works. (To make them accessible to a wider audience, English supertitles are used during… Chicago Shakespeare Theater
This group's home on Navy Pier is a visually stunning, state-of-the-art jewel. The centerpiece of the glass-box complex, which rises seven stories, is a 525-seat courtyard-style theater patterned loosely after the Swan Theater in Stratford-upon-Avon. The complex also houses a…- Classical
Chicago Symphony Orchestra
The Chicago Symphony Orchestra is considered among the best in the world; a legacy of the late maestro Sir Georg Solti, who captured a record-breaking 31 Grammy awards for his CSO recordings and showcased the orchestra at other major musical capitals during frequent overseas tours.… City Winery
This West Loop restaurant, winery, and concert venue burst onto the music scene in 2012, bringing in night after night of acts that critics—and fans—absolutely love, from blues and jazz to folk and hip hop, rock, country, and more. Prince, Sinead O’Connor, Lucinda Williams, Billy…- Comedy Clubs
ComedySportz
Comedy without the F-bomb? Okay, so occasionally one slips out, but at this family-friendly club, the perp is given a “Brown Bag Foul” by the ref. Yes, ref. Teams compete in this laugh-a-thon for audience applause, and the one that earns the most laughs wins. Most of the improv is… Coq d’Or
Enter this old-school piano bar, with its dark woods and deep leather booths, and you know you’re seeing the same scene your grandparents did, when this was one of Chicago’s hot spots. This lounge showcases pianists and vocalists on weekends, from 9pm to 1am Friday and Saturday. It’s…- Bars & Pubs
Corcoran’s
Irish pubs are a dime a dozen in Chicago, where Irish pride runs strong. But Corcoran’s manages to stand out in the crowd, thanks to a daily beer specials, a hugely popular beer garden during the warm months, and its proximity to Second City, which is across the street. You’ll find a… Court Theatre
Given its affiliation with the University of Chicago, it should come as no surprise that this theater knows its way around the classics, from Molière to Ibsen. The productions here, however, are far from stuffy academic exercises: The vibrant, energetic takes on well-known works draw…- Jazz
Elbo Room
Upstairs, Elbo Room looks like any other low-key Lincoln Park watering hole, but in the basement you'll find a delightfully eclectic live music venue; in any given week, the lineup could include rockabilly, hip-hop, soul, funk, and more. The subterranean setting is cozy and brings… - Gay & Lesbian Bars
Elixir
You won’t find a shower competition or show tune sing along here. Instead, you’ll discover something that is all too often missing on the gummy-bear-shot-filled Chicago gay bar circuit: craft cocktails, which have made Elixir a welcome newcomer to the scene. This tiny Boystown lounge… Facets Multi-Media
This nonprofit group screens independent and experimental films from around the world at its modest Cinematheque Theatre. Its collection of children’s films is the most extensive in the U.S., and it also hosts the Chicago International Children’s Film Festival (Oct/Nov), the oldest…Factory Theater
This irreverent young troupe offers the quintessential low-budget Chicago theater experience. The group specializes in original works written by the ensemble, many of which aim at a young, nontheatrical crowd. (You're encouraged to bring your own beer and drink it during the…Gene Siskel Film Center
Named after the late Chicago Tribune film critic, this theater for serious film buffs is part of the School of the Art Institute of Chicago. It offers an array of foreign, art, and experimental films, as well as lectures and discussions with filmmakers.Goodman Theatre
The Goodman, under artistic director Robert Falls, is the top dog of the Chicago theater scene, producing both original shows and familiar standards. (Some of its high-profile productions, including acclaimed revivals of Arthur Miller's Death of a Salesman and Desire Under the Elms,…- Bars & Pubs
Goose Island Brewing Company
This brewpub was making craft beer well before the recent renaissance. Relax in the taproom, where there’s a full food menu with suggested beer pairings, or take the informative, hour-long tour ($12; yes, there’s beer along the way). The brewery was acquired by Anheuser-Busch a few… Grant Park Orchestra and Chorus
One of the city's best cultural bargains, this music festival offers a series of free outdoor classical music concerts from June through August. The symphony, along with internationally known musicians and singers, performs in the gorgeous Frank Gehry-designed Pritzker Music Pavilion…Green Mill
The Green Mill is the most authentic jazz club in the city, hands down. People don’t come here to socialize (and if they do, they may get hushed), they come for good, solid jazz. The sultry but bare-bones jazz club, which started as a roadhouse in 1907, used to be an Al Capone…- Bar
Half Acre
Daisy Cutter has long been Chicago-speak for “craft beer.” Drink the piney pale ale and other inspired brews right where they were created, at this small but mighty North Side brewery and taproom. There’s a second location a couple of miles north.North Center - Bar
Headquarters Beercade
The beercade/barcade scene—think arcade with adult beverages—is booming in Chicago, and this location is the most convenient for visitors. Suck on a boozy “freezer pop” while playing Centipede or 60-plus other vintage games. If you work up an appetite, there’s also a full food menu.River North - Bars & Pubs
Hopleaf
There are so many neighborhood bars in Chicago that it takes something special for a tavern’s name to carry beyond the zip code. Andersonville’s Hopleaf has that something special. You’re likely to find as many people who walked here as you are to see commuters, interested in… - Jazz
House of Blues
The largest location in a national chain of music venues, the House of Blues could more appropriately be called the House of Pop. Although it's decorated with Mississippi Delta folk art, the bands that play here tend to be rock groups, '80s novelty acts, and the occasional hip-hop or… - The Performing Arts
Hubbard Street Dance Chicago
If you don’t think dancers are athletes, check out a performance by Hubbard Street Dance, and then come talk to me. The muscular performances, which are as diverse as they come, make you feel alive, and even the rhythmless get the wiggles. Every season, this Chicago favorite outdoes… - Performing Arts Venue
Jay Pritzker Pavilion
Gospel, jazz, salsa, world music, rock, classical—you name it and you’re likely to find it at this beloved outdoor venue at Millennium Park during the summer. See website for concert dates. Jazz Showcase
This is the oldest jazz club in town (since 1947), and it has hosted a who’s who of jazz greats: Count Basie, Dizzy Gillespie, Stu Katz, and the list goes on. It also may be the most tidy of jazz clubs in town, putting on shows that feel like concerts, rather than bar sets. The place…- The Performing Arts
Joffrey Ballet of Chicago
Founded in 1956 in New York, the Joffrey moved into the Joffrey Tower in 2008, and does about 6 weeks of performances in its hometown, including the ever popular Nutcracker in December. If you’ve always dreamed of dancing like the pros, you can drop in on an adult dance class at… - Coffee Houses
Julius Meinl
Austria's premier coffee roaster chose Chicago -- and, mysteriously, a location near Wrigley Field -- for its first U.S. outpost. The result is a mix of Austrian style (upholstered banquettes, white marble tables, newspapers hanging on wicker frames) and American cheeriness (lots of… Kingston Mines
Open since 1968, Kingston Mines was the first blues joint to open on the North Side of racially segregated Chicago. The crowd here changes, depending on who’s playing, but with its proximity to DePaul University, you can count on an exuberant youthful crowd on the prowl for Bacardi…Late Night Catechism
Catechism class is in session every weekend (though not late-night) at this long-running show where you can laugh your sins off. Audience participation is part of the experience, so be prepared to make your own true confessions to the nuns.Lincoln Hall
You know how some concert venues just make you feel old, in contrast to the grunge-loving youth? Lincoln Hall is a place where you’ll never feel that way. This two-level Lincoln Park hall brings in some mid-level names in rock, hip hop, folk, alternative, and alt-country, and has…- Bars & Pubs
Lone Wolf
Seems every block in just about every neighborhood in Chicago has a dive bar that could pass as any dive bar. Outside, there’s red brick and frosted windows, along with a generic beer sign. Lone Wolf is a new, playful take on that neighborhood bar, capturing each of those elements,… - Bars & Pubs
Longman & Eagle
Confession: I never feel quite cool enough to fit in at Longman & Eagle, where the young and beautiful staff all seem to wear oversized hipster glasses and have a slightly detached air. Whiskey, of course, helps alleviate that out-of-place sense, and Longman & Eagle offers… Lookingglass Theatre Company
One of the most visually oriented companies in town, Lookingglass produces original shows and unusual literary adaptations in a highly physical, imaginative style. These shows emphasize the look of a show as much as the acting, whether it's having performers wade through a giant…- Bar
Lost Lake
If you assume tiki drinks are overly sweet, think again. Lost Lake serves fruit-forward, strong, balanced cocktails in a bar filled with bamboo and palm fronds. The banana daiquiri is even topped with a banana cut to look like a dolphin.Logan Square - Opera
Lyric Opera of Chicago
One of the top American opera companies, the Lyric attracts the very best singers in the world for its lavish productions. Opening night in September remains the quasi-official kickoff of the Chicago social season, but don't be scared off by the snooty factor; audiences here are… - Bars & Pubs
Miller’s Pub
It’s not easy to find a welcoming spot filled with regulars inside the Loop, where restaurants and bars often struggle to draw a nighttime crowd after workers go home. Miller’s has done just that—and kept its beer prices low—since it opened in 1935. It’s the closest thing you’ll find… - The Performing Arts
Muntu Dance Theatre of Chicago
The brilliantly colorful costumes and booming drums transport you from the Harris Theater across Africa and into the Caribbean with Muntu, a traditional African dance company that’s been operating longer than any other of its kind. The barefoot moves pay homage to both tribal and… Music Box Theatre
This atmospheric movie house, designed to re-create the open-air feeling of an Italian courtyard, opened in 1929. Its funky, shabby feel is part of its charm. The now-restored theater screens cult, independent, classic, and foreign films.- Performing Arts Venue
North Shore Center for the Performing Arts
Opened in 1996, this state-of-the-art complex has earned comparisons to Washington, D.C.’s Kennedy Center. It’s home of the respected Northlight Theater, the Skokie Valley Symphony Orchestra, an educational arts series touring acts, including comics, dance troupes, and children’s… - Bars & Pubs
Old Town Ale House
First, the art. The primary eye-catcher is a portrait of a nude Sarah Palin, toting a machine gun, standing on a bear rug. Then there’s former Illinois governor turned federal prisoner number 40892-424, Rod Blagojevich, stripping down in his orange jumpsuit for a cavity search. And… - Jazz
Old Town School of Folk Music
Country, folk, bluegrass, Latin, Celtic -- the Old Town School of Folk Music covers a spectrum of indigenous musical forms. Best known as a training center offering a slate of music classes, the school also plays host to everyone from the legendary Pete Seeger to bluegrass phenom… - Bar
Parson’s Chicken & Fish
This gas station-turned-bar-and-fried-chicken-shack brought to Chicago the Negroni slushy, and for that, the town is grateful. Weather-permitting, the boozy slushies, beer cocktails, and even Parson’s own eponymous beer are best sipped on the enormous patio, which is loaded with…Logan Square - Bar
Plymouth
There’s no theme, no dress code, no fancy cocktail menu. Plymouth is just a good, friendly, no-frills bar with solid drink specials and friendly servers. Thanks to its central Loop location, it’s popular with the after-work crowd—especially in the summertime, when it’s nice enough to…The Loop - Wine bar
Pops for Champagne
A hot date spot for all ages, this romantic lounge offers more than 250 labels of bubbly, plus free, live jazz at 9pm (Sun–Tues) in the downstairs jazz lounge. Bottles of sparkling start at $55. With a courtyard and sidewalk cafe, raw bar, jazz lounge—Pops has it all. - Performing Arts Venue
Ravinia Festival
Want to know where the natives get away from it all? Come summertime, you’ll find them chilling on the lawn at Ravinia, the seasonal home of the highly regarded Chicago Symphony Orchestra in suburban Highland Park. In operation since 1904, Ravinia started off as an amusement park.… Redhead Piano Bar
Men and women, usually 40 and up, dress to the nines at this old-school piano bar, where those wearing sneakers and hats are turned away. Expect to sing along to lots of Elton John and Billy Joel, and plan on getting to know your neighbors. Seats are close together and the crowd is…- Gay & Lesbian Bars
Replay
Grab a brew from one of the cute, scruffy bartenders and get your quarters ready. Replay is home to about a dozen classic games, like Frogger, Centipede, Super Mario Bros., and a couple of pinball machines, and many of them are even free. The young, energetic crowd alternates between… - Bars & Pubs
Revolution Brewpub
One of Logan Square’s largest and most popular spots, the bar here gets packed with artsy neighbors, even during mid-week lunch hour, and you can pretty much forget getting in in under an hour Friday or Saturday. The loud brewpub is filled with raised fists—the symbol of… Rosa’s Lounge
It’s a bit of a hike to this Logan Square blues dive, but if you’re already in the area, stop in and see what a hipster-filled blues bar looks like. This hole-in-the-wall, which is not much more than a long, skinny room, has been here for more than 3 decades. Shows usually start at…- Gay & Lesbian Bars
Roscoe’s Tavern
A mainstay in the gay and lesbian community since it opened in 1987, Roscoe’s, which is located in the heart of Boystown, is a casual spot for a weekday beer or a rollicking weekend party that gets more crowded as the clock ticks on. Despite the crowds, which span the generations and… - Bar
Sable Kitchen & Bar
The outstanding happy hour might lure people in ($6 cocktails from 4–6pm during the week), but it’s the book-length booze list and chatty bartenders that keep them at this bar at the Hotel Palomar. Judging by the ratio of locals to visitors, you’d never guess it’s a hotel bar.River North Schubas Tavern
This small, neighborhood concert venue is a favorite for indie rock, country, and folk fans. In an intimate hall, with room for just 165 concertgoers, every single seat is a winner here, and acts fill the stage 7 nights a week, with tickets usually going for $20. Some are big names,…- Gay & Lesbian Bars
Sidetrack
Slushies and show tunes are the name of the game here. Sidetrack is a huge bar filling eight storefronts and a rooftop deck, where flirty patrons (and flirty bartenders) sip on supersweet frozen drinks (Midori melon ball, Bacardi Pineapple Mai Tai, Effen Black Cherry Buzz, you get… - Bar
Signature Lounge
Skip the ticket and line for 360 CHICAGO, which is the observation deck on the 94th floor of the John Hancock Building, and just head to this 96th floor lounge. Order a martini and soak in the views.Magnificent Mile - Dance Clubs
Smart Bar
A long-established name on the dance circuit, Smart Bar, tucked in the basement below the rock club Metro, spins the latest musical forms, from underground house and punk to ethereal and gothic. The scene starts late, and the dancing denizens vary widely, depending on which bands are… Steppenwolf Theatre Company
Once a pioneer of bare-bones guerilla theater, Steppenwolf has moved firmly into the mainstream with a state-of-the-art theater and production budgets that rival those in any big city. The company has garnered 12 Tony Awards and launched the careers of several respected and…- Bars & Pubs
Terrace 16
A cocktail here will run you at least $15, but the views from the 16th floor terrace, which include the Wrigley clocktower, Tribune Tower, and the neighboring Chicago skyline, are totally worth the price of admission. Expect long waits Wednesday and Saturday nights, when locals and… - Bars & Pubs
The Aviary
Attached to Next restaurant in the West Loop and co-owned by renowned Chicago chef Grant Achatz, the Aviary is a libations laboratory that puts a touch of molecular gastronomy into every drink. When you enter, you’ll get a glimpse of the chemists at work, inside what looks like a… The Baton Show Lounge
A taste of Vegas in Chicago? Sure, why not. You might want to wear a little extra lipstick tonight if you hope to outshine the drag queens here. The Baton Show Lounge has been staging raucous performances for more than 45 years now, and bachelorettes go crazy for it. Expect large…- Bars & Pubs
The Berkshire Room
Tucked inside the super hip Acme Hotel, The Berkshire Room is one of the more mellow bars in the River North area. Dim and casual, but not dive-ish in the slightest, you can get just about any libation you can think of, from inexpensive beers, like Miller Lite, to “Dealer’s Choice”… - Gay & Lesbian Bars
The Closet
The “Cheers” of the neighborhood, this tiny but comfortable neighborhood dive bar has been a lesbian (and gay and hetero) favorite since owners Judi and Rose opened it in 1978. Grab a bucket of beers, some darts, and settle in for an evening with friendly regulars. If the bartender… - Bars & Pubs
The Cubby Bear
Located across from Wrigley Field, the party following a Cubs game spills into the enormous Cubby Bear. It’s not for everyone, and if you do go, get your elbows ready to fend for space from drunken baseball fans. Still, throwing one back at the Cubby Bear is practically a rite of… - The Performing Arts
The Dance Center–Columbia College Chicago
As an arts school, Columbia’s performances are reliably fresh, and the styles from troupes from around the world (and from the college) may include West African, break dancing, tap, jazz, Bollywood, and more. The setting is a 275-seat theater housed in an Art Deco building from the… The Empty Bottle
Remember the first live show you ever saw in a bar? The Empty Bottle, located in Ukrainian Village, a bit south of Wicker Park, will take you back to that. A tad grungy, with Christmas lights above the bar and weird, doll head art on the walls, this place brings in alt rock and alt…The Hideout
Head to this friendly, downhome tavern for the best lineup of folk and alt country bands in the city. Located in an old house, in a just out-of-the-way-enough industrial area, The Hideout draws in crowds nightly. If there’s no music playing at the small venue in this friendly dive…The House Theatre
If you're looking for the up-and-coming stars of Chicago theater, keep your eyes on the House. This group of young actors takes on big themes (Harry Houdini and his obsession with death, the space-age tales of Ray Bradbury) and turns them into nonstop spectacles of drama, music, and…The Infinite Wrench
If you don’t like the performance, wait a minute—actually, 2 minutes—and it’ll change. So it goes with this spirited production, which consists of a series of 2-minute plays, one after another, all written by ensemble members. Drama, comedy, surrealism—it’s all here.- Bars & Pubs
The J. Parker
If you’re lucky enough to be in Chicago during the warm months, hie thee to the rooftop of Hotel Lincoln, stat. Grab a chair or couch and a glass of rosé and gaze out on Lake Michigan to the east, or the lights of the city all around you. I’ll warn you that service here is less than… - Bars & Pubs
The Map Room
Travel is the key theme at The Map Room, a Bucktown favorite that’s been around since the early '90s. You’ll see it in the maps that line the walls and the flags that hang from the ceiling. More importantly, you’ll taste it in the 200-plus beers that the bar offers, with far-flung… - Comedy Clubs
The Second City
Ah, the crown jewel of comedy in Chicago, and well deserved, at that. Second City launched the careers of hundreds of famous side-splitters. If you’re going to hit one comedy show in Chicago, make it this one. There’s a reason there’s a comedy school here, and that comedy scouts are… - Bars & Pubs
The Violet Hour
Yes, it’s another speakeasy-style bar, but Violet Hour was one of the early ones to explore the Prohibition-era theme, and it takes it so seriously that newcomers might struggle to find the door, which isn’t marked with a sign. Have no fear, though, you’ll know the Violet Hour by the… - Nightclub
The Whistler
Part music venue, part record label, all cocktail destination, this Logan Square lounge is as surprising as they come, with DJs and live entertainment nightly. Theatre on the Lake
What a great way to see two of the city's signature strengths: a sublime skyline view from the water's edge and an evening of off-Loop Chicago theater. The Prairie School-style building, built in 1920 as a sanitarium for babies and children suffering from tuberculosis, has hosted…- Bars & Pubs
Three Dots and a Dash
You have to be in the know to find this hidden tiki bar. The actual address listed will take you to a more typical River North bar, called Bub City. Instead, head to the alley between Hubbard and Illinois streets. You’ll see a blue light cast on a brick building and a Three Dots and… Tommy Gun’s Garage
A cut above the usual tourist fare, this dinner theater puts on a vaudeville show filled with 1920s-era gangsters, flappers, and gigolos. The food’s not bad, either, but hooch (alcohol, silly) will cost you extra.Trap Door Theatre
Trap Door is emblematic of the streetwise, no-holds-barred brand of off-Loop theater. A risk-taking, emotionally high-voltage company that has somehow stayed afloat (despite performing in a converted garage hidden behind a Bucktown restaurant), Trap Door concentrates on plays with a…- Bars & Pubs
Travelle Bar and Lounge
This midcentury-modern-style lounge, located on the second floor of the Langham Hotel, has cozy, curvy couches, comfortable chairs, dim lighting, and an air of sexy chic. Nestled in the former IBM building, a landmark designed by architect Ludwig Mies van der Rohe, the lounge is… - Bars & Pubs
Uncommon Ground
This bar and restaurant is a reminder that not all of Wrigleyville is Cubs crazy, and, in fact, it’s possible to enjoy a nice glass of wine while listening to self-contained musicians on weekends. Grab a seat in the living-room-like interior, or, if you still want one hand in the… Victory Gardens Theater
Victory Gardens is one of the few pioneers of independent theater that has survived since the 1970s. The company was rewarded for its unswerving commitment to developing playwrights with a Tony Award for regional theater in 2001 -- a real coup for a relatively small theater. The five…- Comedy Clubs
Zanies Comedy Club
Yes, it’s not-so-coincidentally located about a block from Second City, but don’t be too quick to assume you’ll get sloppy seconds at Zanies. This comedy club holds its own, bringing in national headliners (Ari Shaffir, formerly of Comedy Central’s This is Not Happening, has appeared… - Jazz
Zebra Lounge
The most quirky piano bar in town, Zebra Lounge has a loyal following despite (or maybe because of) the campy decor. Just as you would expect, black-and-white stripes are the unifying element at this dark, shoebox-size Gold Coast spot, furnished with black vinyl booths, a small… - Comedy Clubs
iO Theater
Tina Fey and Amy Poehler got their start here, and the remarkable improv talent streak continues today across four stages. Get ready for laughter exhaustion.
More To Do in Chicago
Best Free Things to Do in Chicago
Exploring Millennium Park: This downtown park, carved out of the northwest corner of Grant Park, is one of the city's best spots for strolling, hanging out, and people-watching. (Bonus: It's an easy walk from downtown hotels.) While the Pritzker Music Pavilion, designed by Frank…
The Best Websites in Chicago
League of Chicago Theatres (www.chicagoplays.com): If you're planning to catch a show while in town, visit this comprehensive theater site, where you can search specific dates to see what's playing.Metromix (www.chicago.metromix.com): Operated by the Chicago Tribune, this site…
