Frank Sinatra once proclaimed Chicago his kind of town. It will be yours as well. Awaiting you in the Windy City are new discoveries and favorite places you’ll want to visit again and again, from riding the “El” to singing along with the crowds at Wrigley Field’s seventh-inning stretch. In this section, I describe some quintessential Chicago experiences that just might become part of your family’s vacation lore. They’ll make Chicago your kind of town, too.

1. Take yourself out to the ballgame at Wrigley Field. Our historic ballpark approaches perfection with its ivy-covered walls, hand-operated scoreboard, and view of the jade-colored, glassy waters of Lake Michigan from the upper decks. The Cubs play night games, but Wrigley is best experienced on a summer afternoon, when you’ll be surrounded by plenty of natives playing hooky from work—a Windy City tradition. 

2. Take a ride on our famous “El” train. Our elevated train is not only the least expensive ride in town, but it’s also a great way to get a birds-eye glimpse of Chicago. For the best views, board the Brown Line at Washington/Wells, and ride it around the Loop through the canyons of office buildings (you’ll be close enough to peer into some of them). It’ll take less than 30 minutes of your touring time, it’s inexpensive, and kids love it. 

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3. Sample the Midwest’s best farm-grown foods at the Chicago Green City Market. Founded by prominent Chicago chefs, this Lincoln Park market allows regular folks to buy the same organic and sustainably grown foods that will appear on plates in the best restaurants in town. There’s music, live cooking demonstrations, and a chance to sample French-style crepes made to order with market ingredients. 

4. Marvel at the intricate pointillism of Seurat’s A Sunday on the Island of La Grande Jatte and other masterpieces at Chicago’s grande dame of museums, the Art Institute. You’ll find Seurat’s work in the renowned Impressionist collection, which also features one of the world’s largest displays of Monet paintings. Your second stop should be the collections of European and American contemporary art, home to works by Picasso, Matisse, Dalí, Pollock, and Warhol.

5. Get the blues at one of the city’s many great music joints. At B.L.U.E.S., stellar female performers are the draw. At Buddy Guy’s Legends, the Louisiana-style soul food and barbecue makes it worth arriving early and settling in for the evening. If you visit Chicago in January, don’t miss out on a performance by the legendary guitarist who owns this place; but book ahead—the shows sell out well in advance.

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6. Stroll the lakefront and ogle our inland ocean. Chicago’s forefathers had the foresight to keep the city’s 26 miles of lakefront free and clear of development. As a result, you can bike, rollerblade, jog, or walk along Lake Michigan and enjoy a chain of parks that includes Chicago’s signature Lincoln Park and Grant Park. 

7. Admire our renowned skyline on a boat cruise along the Chicago River and Lake Michigan. The best way to get a perspective on Chicago’s history and learn about the dramatic buildings that form the city’s skyline is to take an architecture boat tour. Some of the best are run by the Chicago Architecture Center, covering some 40 buildings with entertaining and enlightening narrative from an army of well-versed docents. 

8. Check out the wares on the Magnificent Mile. Shopping is the thing on Michigan Avenue, and you can easily while away a day browsing and buying your way up the avenue. Other areas of the city offer chic boutiques and hard-to-find antiques and vintage clothing, but for a huge selection offering something for everyone, the Magnificent Mile is your best bet. 

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9. Explore the outdoor architectural museum that is Oak Park. If you have a passion for architecture or literature, you’ll find plenty of sights to see in this suburb on the western border of the city. Ernest Hemingway was born here, and his home offers insight into Oak Park’s most famous native son. But most visitors are drawn to the Frank Lloyd Wright Home & Studio, and to the homes lining Oak Park’s well-maintained streets that the famous architect designed. 

10. Share a laugh at The Second City. Training ground for the country’s best comedians, The Second City excels in long-form improvisational comedy. Ensembles change frequently, so check the local newspapers for reviews of the latest offering. And, if you like your history mixed with humor (and who doesn’t?), don’t miss The Second City’s Neighborhood Tour of Old Town, which gives you a glimpse into the neighborhood’s architecture and history, plus some insider info on Second City alumni and their legendary hangouts and real-life antics. 

11. Grip the edge of your seat at a Chicago theater company performance. Whether you choose a production by the Steppenwolf Theatre Company, Goodman Theatre, or a smaller venue such as Victory Gardens Theater, don’t miss a chance to see what might be the next big hit to move to Broadway. 

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12. Climb aboard a captured U-boat at the Museum of Science and Industry, the granddaddy of interactive museums. The U-505, captured in 1944 and brought to the museum 10 years later, is only one of 2,000 exhibits. It’s easy to spend a day here, especially if you take in an Omnimax movie, located in the Henry Crown Space Center, where you can also hop aboard a simulator to experience a space shuttle flight. 

13. Explore Hyde Park’s Gothic quadrangle and magnificent mansions. Home to the University of Chicago, with its 90-plus Nobel laureates, intimidating buildings with Gothic spires, and hallowed academic halls, Hyde Park is sure to impress. Off campus, Hyde Park is an approachable, cosmopolitan neighborhood that’s home to one of Frank Lloyd Wright’s finest works, the Robie House. 

14. Take in jazz or a poetry slam at Green Mill. This popular watering hole of the 1920s and 1930s still retains its speakeasy vibe. On Sunday night, Green Mill hosts the Uptown Poetry Slam, where poets vie for the open mic. Most nights, though, jazz is on the menu from about 9pm ‘til the wee hours, so sink into a plush velvet booth and enjoy. 

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15. Get snout-to-nose with the baby belugas at John G. Shedd Aquarium. The world’s largest indoor aquarium is a city treasure. Don’t miss the Aquatic Show at the Oceanarium, which re-creates a Pacific Northwest coastal environment and features a wall of windows that reveals the lake outside and creates the illusion of one uninterrupted expanse of sea (that’s where you’ll find those baby belugas and dolphins). Another all-time favorite is watching the diver feed the sea creatures in the Caribbean Reef during the free shows four times daily.

16. Interact with the sculpture at Millennium Park, the city’s urban showpiece and one of its most popular tourist attractions. Pay a visit to Cloud Gate, the huge elliptical sculpture by British artist Anish Kapoor, in which you can examine your reflection in fun-house-like distortions. While you’re here, make sure to catch a show at the stunning Frank Gehry–designed Pritzker Music Pavilion, home to free summer concerts performed by the Grant Park Symphony Orchestra. 

 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.