The Top Shopping Streets & Neighborhoods

Wicker Park/Bucktown Shopping

The nickname "Magnificent Mile" -- hyperbole to some, an understatement to others -- refers to the roughly mile-long stretch of North Michigan Avenue between Oak Street and the Chicago River.

The density of the area's first-rate shopping is, quite simply, unmatched. Even jaded shoppers from other worldly capitals are delighted at the ease and convenience of the stores concentrated here. Taking into account that tony Oak Street is just around the corner, the overall area is a little like New York's Fifth Avenue and Beverly Hills's Rodeo Drive rolled into one. Whether your passion is Bulgari jewelry, Prada bags, or Salvatore Ferragamo footwear, you'll find it on this stretch of concrete. And don't think you're seeing everything by walking down the street: Michigan Avenue is home to several indoor, high-rise malls, where plenty more boutiques and restaurants are tucked away. Even if you're not the shop-till-you-drop type, it's worth a stroll because this stretch is, in many ways, the heart of the city, a place that bustles with life year-round (although it's especially crowded around Christmas and during the summer).

For the ultimate Mag Mile shopping adventure, start at one end of North Michigan Avenue and try to work your way to the other.

A North Michigan Avenue Shopper's Stroll

This shopper's stroll begins at Oak Street at the northern end of the avenue and heads south toward the river. It just hits the highlights; you'll find much more to tempt your wallet as you meander from designer landmarks to well-known chain stores. (In general, this is not the place to pick up distinctive, one-of-a-kind items -- other neighborhoods cater more to shoppers searching for something unique.)

The parade of designer names begins at the intersection of Michigan Avenue and Oak Street, including a couple housed in The Drake Hotel, such as the legendary Danish silversmith Georg Jensen, 959 N. Michigan Ave. (tel. 312/642-9160), known for outstanding craftsmanship in sterling silver and gold, including earrings, brooches, watches, tie clips, and flatware; and Chanel, 935 N. Michigan Ave. (tel. 312/787-5500). One block south is another luxury emporium, the spacious Louis Vuitton store at 919 N. Michigan Ave. (tel. 312/944-2010), where you'll find trendy handbags and the company's distinctive monogrammed luggage.

On the other side of the street, opposite the dark, soaring Hancock Building, you'll find a quiet oasis that's worth a quick peek. The Fourth Presbyterian Church, 126 E. Chestnut St. (tel. 312/787-4570), looks like something out of an English country village, with a Gothic stone exterior and a peaceful, flower-filled courtyard (perfect for escaping the Mag Mile crowds for a few moments).

One block south, you'll notice a steady stream of mothers and daughters toting distinctive red shopping bags from American Girl Place, on the ground floor of the Water Tower Place mall, 835 N. Michigan Ave. (tel. 877/AG-PLACE). The multi-story doll emporium is one of the most-visited attractions in town, thanks to the popularity of the company's historic character dolls. A stage show brings stories from the American Girl books to life, and the store's cafe is a nice spot for a special mother-daughter lunch or afternoon tea.

Across the street, overlooking a small park next to the historic Water Tower, is Giorgio Armani's sleek boutique, 800 N. Michigan Ave., in the Park Hyatt Hotel (tel. 312/573-4220). Offering an alternative to high-style minimalism is the Hershey's Chicago candy store, 822 N. Michigan Ave. (tel. 312/337-7711), a multi-sensory overload of colors and chocolate.

The next block of Michigan Avenue has a New York vibe, thanks to the world's largest Polo Ralph Lauren, 750 N. Michigan Ave. (tel. 312/280-1655), a four-floor, wood-paneled minimansion, and Tiffany & Co., 730 N. Michigan Ave. (tel. 312/944-7500), with its signature clock, jewels, and tabletop accessories. (To get your hands on one of the coveted robin's-egg blue shopping bags without spending a fortune, pick up one of the $80 sterling-silver key chains -- the least expensive items in the store).

A few doors south are Neiman Marcus, 737 N. Michigan Ave. (tel. 312/642-5900), and at 669 N. Michigan Ave. (tel. 312/642-6363), the hugely popular Niketown, a multilevel complex that helped pioneer the concept of retail as entertainment. Across the street, you'll probably see a line of people trailing out from the Garrett Popcorn Shop, 670 N. Michigan Ave. (tel. 312/944-2630), a 50-year-old landmark. Join the locals in line and pick up some caramel corn for a quick sugar rush.

At the intersection of Michigan Avenue and Erie Street is the appropriately barrel-shaped Crate & Barrel, 646 N. Michigan Ave. (tel. 312/787-5900). Crate & Barrel was started in Chicago, so this is the company's flagship location. Countless varieties of glassware, dishes, cookware, and kitchen gadgets for everyday use line the shelves. The top two floors are devoted to furniture.

Continuing south, you'll find Burberry, 633 N. Michigan Ave. (tel. 312/787-2500), where the classic beige plaid shows up on chic purses, shoes, and bathing suits (if you're looking for luxury souvenirs, check out the collection of baby clothes and dog accessories). Beautifully made (but pricey) Italian lingerie is the draw at La Perla, 535 N. Michigan Ave. (tel. 312/494-0400), a popular stop around Valentine's Day.

Resting at Crate & Barrel -- Need a quick break during your shopping spree? The overstuffed couches on the third and fourth floors of Crate & Barrel practically beg to be tested out -- and there are always at least a few weary shoppers slumped against the piles of pillows. Go ahead and rest awhile; the store's staff won't bug you. Make sure you stop by the terrace on the fourth floor for a bird's-eye view of Michigan Avenue, and enjoy a moment of contemplation before rejoining the hordes below.

The Magnificent Malls

Many of the Magnificent Mile's shops are hidden inside high-rise malls, most of which take up a whole city block.

Lunch on the Mag Mile -- When I worked just off Michigan Avenue, my favorite spot for lunch was the food court on the eighth floor of Chicago Place. A bright, airy space with a fountain and palm trees, it's my pick for the best cheap eats in the area, especially if you're traveling with kids. The cuisine may be uninspired -- food choices include Subway, Taco Bell, McDonald's -- but the setting makes this a few steps above the average mall food court. If you're lucky, you can even snag one of the tables overlooking Michigan Avenue, the kind of view that costs big bucks at the city's luxury hotels.

Chic Shopping on Nearby Oak Street

Oak Street has long been a symbol of designer-label shopping; if a store has an Oak Street address, you can count on it being expensive. The shopping district itself is actually quite limited, taking up only 1 block at the northern tip of the Magnificent Mile (where Michigan Ave. ends and Lake Shore Dr. begins). While big-name designer boutiques such as Giorgio Armani and Louis Vuitton pride themselves on having a Michigan Avenue address, Oak Street features smaller, more personal shops (most of them high-priced). Since most of the stores are tucked into converted town houses, it also has a more tranquil feel than Michigan Avenue. It's well worth a stroll for people-watching: This is Main Street for Chicago socialites. Most of Oak Street is closed on Sunday, except during the holiday season.

Chicago's most high-profile clothing boutique, Ultimo, is right around the corner from Michigan Avenue; upscale and exclusive, it caters to the seriously fashionable. Footwear fans can browse Italian shoemaker Tod's, best known for its luxuriously soft (and pricey) driving shoes. Shoes, stationery, and handbags are available at kate spade, 101 E. Oak St. (tel. 312/654-8853), along with the Jack Spade line of men's accessories. The priciest accessories on this very pricey block can likely be found at French luxury house Hermès of Paris, 110 E. Oak St. (tel. 312/787-8175). Thread-count fanatics swear by the sheets from Pratesi, 67 E. Oak St. (tel. 312/943-8422), and Frette, 41 E. Oak St. (tel. 312/649-3744), both of which supply linens to top hotels (and where sheet sets cost more than what some people pay in rent).

Anchoring the western end of the block are two haute heavyweights, hip Italian designer Prada, 30 E. Oak St. (tel. 312/951-1113), which offers three floors of sleek, postmodern fashions for men and women and plenty of the designer's signature handbags; and equally style-conscious Barneys New York.

An Oak Street Bargain -- Oak Street is not the place to come shopping for bargains -- with one exception -- Bravco, 43 E. Oak St. (tel. 312/943-4305). This crowded, narrow drugstore seems out of place among the hip boutiques, but it's a popular spot among Chicago hairstylists and makeup artists. You'll find an excellent selection of professional hair and beauty products (including Aveda, Sebastian, and Bumble and Bumble) here for much less than they cost at salons. Even if you haven't heard of some of the brands, trust me, if Bravco carries them, they're hot.

State Street & the Loop

Shopping in the Loop is mostly concentrated along State Street, from Randolph Street south to Congress Parkway (although there are stores sprinkled elsewhere, they're mostly places that cater to office workers: drugstores, sandwich shops, and chain clothing stores). State Street was Chicago's first great shopping district -- by World War I, seven of the largest and most lavish department stores in the world were competing for shoppers' loyalties along this half-mile stretch. The area has been eclipsed by Michigan Avenue, but one grand old department store makes it worth a visit: Macy's at State Street (formerly Marshall Field's), 111 N. State St., at Randolph Street (tel. 312/781-1000). A city landmark and one of the largest department stores in the world, it occupies an entire city block and features the largest Tiffany glass mosaic dome in the U.S. If you're in Chicago between Thanksgiving and New Year's, Macy's has maintained a long-time Marshall Field's tradition: lavishly decorated holiday windows and lunch under the Great Tree in the store's restaurant, the Walnut Room.

Aside from Macy's, State Street has become a hot destination for bargain hunters in recent years, thanks to the opening of discount stores such as Loehmann's, 151 N. State St. (tel. 312/705-3810), Nordstrom Rack, 24 N. State St. (tel. 312/377-5500), T.J. Maxx, 11 N. State St. (tel. 312/553-0515), and Filene's Basement, 1 N. State St. (tel. 312/553-1055). If you've got the energy to hunt through racks of not-so-great stuff, you can sometimes find good designer-label deals.

State Street has a no-frills aura compared to Michigan Avenue -- but it stays busy thanks to the thousands of office workers who stroll around during their lunch hour or after work. On weekends, the street is considerably more subdued.

Point Zero -- If the quick change from north to south in the Loop confuses you, keep in mind that in Chicago, point zero for the purpose of address numbering is the intersection of State and Madison streets.

Jewelers' Row -- It's not quite as impressive as the Big Apple's diamond district, but Chicago's own "Jewelers' Row" is certainly worth a detour for rock hunters. Half a dozen high-rises along the Wabash Avenue El tracks in the heart of the Loop service the wholesale trade, but the one at 5 S. Wabash Ave. opens its doors to customers off the street. There's a mall-like retail space on the ground floor crammed with tiny booths manned by smooth-talking reps hawking their wares. You can grab a map here for a self-guided tour of the rest of the building's tenants. It's quite an experience because many of the booths are closet-size cubbyholes with hunched-over geezers who look as if they've been eyeballing solitaire and marquise cuts since the Roosevelt administration -- Teddy, that is.

River North

Since the 1960s, when the Chicago Imagists (painters Ed Paschke, Jim Nutt, and Roger Brown among them) attracted international attention with their shows at the Hyde Park Art Center, the city has been a fertile breeding ground for emerging artists and innovative art dealers. Today, the primary gallery district is concentrated in the River North neighborhood, where century-old, redbrick warehouses have been converted into lofty exhibition spaces. More recently, a new generation of gallery owners has set up shop in the rapidly gentrifying West Loop neighborhood, where you'll tend to find more cutting-edge work. The River North gallery district is an easy walk from many hotels; the West Loop may seem a little farther afield, but it's only a short cab ride from downtown (you can also take the bus, but I'd recommend a taxi at night).

The River North gallery season officially gets underway on the first Friday after Labor Day in September. Besides fall, another great time to visit the district is from mid-July through August, when the Chicago Art Dealers Association presents Vision, an annual lineup of programs tailored to the public. Early September also offers the annual Around the Coyote festival in Wicker Park/Bucktown (call tel. 773/342-6777 for information), when scores of artists open their studios to the public (the name refers to the now-departed Coyote Gallery, which used to stand at the corner of Damen and North aves.).

The Chicago Reader, a free weekly newspaper available at many stores, taverns, and cafes on the North Side, publishes a very comprehensive listing of current gallery exhibitions, as does the quarterly Chicago Gallery News (www.chicagogallerynews.com), which is available free at the city's visitor information centers. Another good resource is the Chicago Art Dealers Association (tel. 312/649-0065; www.chicagoartdealers.org); the group's website has descriptions of all member galleries.

Along with its status as Chicago's primary art-gallery district, River North -- the area west of the Magnificent Mile and north of the Chicago River -- has attracted many interesting home-design shops concentrated on Wells Street from Kinzie Street to Chicago Avenue. My favorites include Manifesto, 755 N. Wells St., at Chicago Avenue (tel. 312/664-0733), which offers custom-designed furniture, as well as imports from Italy and elsewhere in Europe; Mig & Tig, 540 N. Wells St., at Ohio Street (tel. 312/644-8277), a charming furniture and decorative-accessories shop; and Lightology, 215 W. Chicago Ave., at Wells St. (tel. 312/944-1000), a massive lighting store that carries a mind-boggling array of funky lamps, chandeliers, and glowing orbs from more than 400 manufacturers (even if you have no intention of flying home with a stack of lamps in your luggage, it's fun to browse).

Looming above the Chicago River at the southern end of River North is the Merchandise Mart, the world's largest commercial building. The massive complex was built in 1930 by Marshall Field & Company and was bought in 1945 by Joseph P. Kennedy (JFK's dad). Although the Kennedys sold the Mart in the late 1990s, there's still a family connection: Christopher Kennedy (son of Robert and Ethel) is the president of the company that runs the complex. The Mart houses mostly interior-design showrooms, which are open only to professional designers. One exception is Luxe Home, a collection of kitchen and bath showrooms on the first floor, all of which are open to the public (and worth a look for interior-design junkies). Public tours of the whole complex are offered once a week, usually on Fridays ($12 adults; tel. 312/527-7762 for dates and reservations).

Armitage Avenue

Hovering between the North Side neighborhoods of Old Town and Lincoln Park, Armitage Avenue has emerged as a shopping destination in its own right, thanks to an influx of wealthy young professionals who have settled into historic town homes on the neighboring tree-lined streets. The main shopping district is concentrated between Halsted Street and Racine Avenue; I'd suggest starting at the Armitage El stop (Brown Line), working your way east to Halsted Street, and then wandering a few blocks north to Webster Street. As you stroll around, you'll get a good sense of the area's strong community spirit, with neighbors greeting each other and catching up on the street corners.

The shops and boutiques here are geared toward a sophisticated, well-heeled shopper and make for great browsing. (Most are suited for female shoppers -- sorry, guys.) You'll find trendy clothing boutiques, including that of local-gal-made-good Cynthia Rowley (808 W. Armitage Ave.; tel. 773/528-6160); jaw-droppingly beautiful home-decor stores; beauty emporiums; and one of my favorite impossible-to-classify gift shops, Art Effect. The upscale pet accessories shop Barker & Meowsky, 1003 W. Armitage Ave. (tel. 773/868-0200), has everything you need to spoil furry family members, including catnip cigars, doggy "sushi," and designer-inspired outfits.

Despite the area's upscale feel, you can snag bargains at some top-notch discount and consignment shops, including Lori's Designer Shoes, McShane's Exchange, Fox's, and The Second Child.

Pamper Yourself

When all that Armitage Avenue shopping gets too exhausting, take a break at one of the beauty stores concentrated within a few blocks of each other on Halsted Street. Endo-Exo Apothecary, 2034 N. Halsted St. (tel. 773/525-0500), lined with vintage wood cabinets, is a peaceful retreat that stocks a number of specialty skin-care and makeup lines; they'll even give you a complimentary makeover. The mood is more flashy and hip at Fresh, 2040 N. Halsted St. (tel. 773/404-9776), where the sleek shelves are filled with skin treatments, at-home spa supplies, and their own line of cosmetics. To get really creative, visit the cozy Aroma Workshop, 2050 N. Halsted St. (tel. 773/871-1985), where you can mix up your own custom-scented body lotions and perfumes. A few blocks south, along Armitage Avenue, you'll find all-natural soaps, creams, and bubble baths at the very fragrant Lush store, 859 W. Armitage Ave. (tel. 773/281-LUSH), and skin-care products from the iconic New York apothecary Kiehl's, 907 W. Armitage Ave. (tel. 773/665-2515). Want makeup that's guaranteed to blend with your skin tone? The technicians at Colorlab Custom Cosmetics, 857 W. Armitage Ave. (tel. 773/525-9086), mix up personalized foundation, lipstick and blush; they'll even store your formula so you can order more later.

Lincoln Park & Lakeview

A few major north-south thoroughfares -- Lincoln Avenue, Clark Street, and Broadway -- are the main shopping streets in both Lincoln Park (south of Diversey Pkwy.) and Lakeview (north of Diversey). Most of the shops cater to young singles who live in the surrounding apartment buildings; you'll find plenty of minimart groceries, some clothing and shoe boutiques, and the occasional used-book store, but not much that's worth a special trip.

Radiating from the intersection of Belmont Avenue and Clark Street is a string of shops catering to rebellious kids on tour from their homes in the 'burbs (the Dunkin' Donuts on the corner is often referred to as "Punkin' Donuts" in their honor). One constant in the ever-changing youth culture has been the Alley, 3228 N. Clark St., at Belmont Avenue (tel. 773/883-1800), an "alternative shopping complex" selling everything from plaster gargoyles to racks of leather jackets. It has separate shops specializing in condoms, cigars, and bondage wear. Tragically Hip, a storefront women's boutique, 931 W. Belmont Ave. (tel. 773/549-1500), next to the Belmont El train stop, has outlasted many other similar purveyors of cutting-edge women's apparel.

You can get plugged into what the kids are reading at Chicago Comics, 3244 N. Clark St. (tel. 773/528-1983), considered one of the best comics shops in the country. Besides the usual superhero titles, you'll find lots of European and Japanese comics, along with underground books and 'zines.

Southport Avenue

West of Lakeview, a few blocks from Wrigley Field, this residential area was considered up-and-coming about 10 years ago; now it's definitely arrived. The mix of restaurants, cool (but not too cool) clothing boutiques, and cafes appeals to the upscale urban families who have flocked to the area (watch out for strollers hogging the sidewalk). It's worth a look if you want to hang out in a neighborhood that's a little more laid-back than the Gold Coast or Wicker Park. Start at the Southport El stop on the Brown Line, and work your way north to Grace Street (round-trip, the walk will take you about half an hour -- but allow more if you're doing some serious shopping or want to stop for lunch). Along the way you'll pass the historic Music Box Theater at 3733 N. Southport Ave. (tel. 773/871-6604), north of Addison Street, which shows independent films from around the world. Two clothing shops catering to hip young women with plenty of disposable income are Krista K, 3458 N. Southport Ave. (tel. 773/248-1967), and Red Head Boutique, 3450 N. Southport Ave. (tel. 773/325-9898), which both stock hot new designers that aren't widely available in Chicago. Shane, 3657 N. Southport Ave. (tel. 773/549-0179), and Jake, 3740 N. Southport Ave. (tel. 773/929-5253), carry more casual clothes for both men and women (think trendy T-shirts and specialty-label denim).

Wicker Park/Bucktown

The gentrification of the Wicker Park/Bucktown area was followed by not only a rash of restaurants and bars but also retailers with an artsy bent that reflect the neighborhood's bohemian spirit. Mixed in with old neighborhood businesses, such as discount furniture stores and religious-icon purveyors, is a proliferation of antique-furniture shops, too-cool-for-school clothing boutiques, and eclectic galleries and gift emporiums. Despite the hefty price tags in many of these shops, the neighborhood still feels gritty -- so come here if you want to feel like you've gotten a real urban fix.

Start at the Damen El stop on the Blue Line, and walk north along Damen to Armitage Avenue to scope out the trendiest shops. If you've got time, some stores are also scattered along Milwaukee Avenue south of North Avenue.

The friendly modern-day Marco Polos at Pagoda Red, 1714 N. Damen Ave., second floor (tel. 773/235-1188), has imported beautiful (and expensive) antique furniture and art objects, including Chinese concubine beds, painted Tibetan cabinets, Burmese rolling water vessels, cast-iron lotus bowls, bronze Buddhas, and Chinese inspiration stones. Design-conscious shoppers head to Stitch for one-of-a-kind, stylish gifts -- the kind of thing you won't find at the mall back home. Damen Avenue is also known for its concentration of independent clothing boutiques, which range from edgy, urban looks at p45 to flirty dresses and skirts at Tangerine. Glance at the not-so-affordable price tags and you'll soon see that Wicker Park has come a long way from its gritty, starving-artist past.

Taking a Break in Wicker Park -- When you're ready to rest your weary self, settle down at a local coffeehouse and soak in Wicker Park's artsy vibe. Earwax Café, 1564 N. Milwaukee Ave. (tel. 773/772-4019), attracts the jaded and pierced set with a no-frills, slightly edgy atmosphere. Half & Half, next to the Damen El stop, 1560 N. Damen Ave. (tel. 773/489-6220), is cozier and more welcoming, although there's not as much room to sit. Both cafes are near the bustling intersection of North, Milwaukee, and Damen avenues -- the heart of Wicker Park -- and draw a steady stream of locals. It's here you'll realize that Wicker Park is really just a small town -- with cooler hair and funkier shoes.

West Division Street

Once home to just a few pioneering restaurants, Division Street is quickly being transformed from a desolate urban landscape to a hot shopping destination. It's a work in progress (you'll still find some boarded-up buildings among the cool boutiques), but for now this is what Wicker Park used to be: a place where rents are still cheap enough for eager young entrepreneurs. Start at the Division El stop on the Blue Line, and head west along Division; most stores are concentrated between Milwaukee Avenue and Damen Avenue (a round-trip walk will take about a half-hour). Along the way, you'll stroll past eclectic clothing and home boutiques, including Habit, which stocks fashions from independent labels, and the hip kids' shop Grow, where eco-conscious urban parents stock up on organic-cotton baby clothes and sustainable-wood furniture. The gorgeously eclectic Porte Rouge, 1911 W. Division St. (tel. 773/269-2800), is filled with French antiques and housewares (they'll even offer you a complimentary cup of tea). The mix of people living here -- from working-class Latino families to self-consciously edgy young singles -- makes the local cafes great for people-watching.