USA: Midwest Chicago, IL
Destination: A Shopper's Guide to Chicago
Heads up: High style is blowing into the Windy City
Taking in the Chicago skyline from the Lincoln Park Zoo's Nature Boardwalk; men's apparel and accessories are sold at Haberdash EDC.
Beneath Chicago’s towering skyscrapers and rumbling L tracks, a world of indie retailers and fashion-forward boutiques awaits. The best way to find it? On foot. Here, a walking guide to three of the city’s top shopping destinations, from the glitzy Magnificent Mile to the tree-and-boutique-lined streets of Lincoln Park to the hipster-chic storefronts of Wicker Park and Bucktown. And don’t be embarrassed to wear comfy shoes. The Midwest may be turning trendy, but it hasn’t lost its warm, anything-goes welcome.

Magnificent Mile and the Gold Coast
Packed with big-name brands and flashy department stores, North Michigan Avenue, aka the Magnificent Mile, is to Chicago what Fifth Avenue is to New York. This is not the land of the unique, but you can still find some real treasures. And the sights alone (the diminutive 1869 Historic Water Tower, the soaring 1970 John Hancock Center) make it worth the trek.

Start three blocks west of Michigan, on Ohio and State Streets, to discover a cluster of stores housed in a most unusual landmark: the Medinah Temple, a Middle Eastern–style Shriner structure built in 1912. Two boutiques of note: Haberdash EDC, which has casual-cool men’s apparel from brands like Gitman Vintage and Reigning Champ (and a barber in a driving cap who offers cuts and shaves in the back), and P.O.S.H., a trove of 1950s–1970s American glassware (from $2) and other vintage tabletop finds mainly from England and France.

You’ll know the Mag Mile’s wide, shopper-packed sidewalks as soon as you hit Michigan Avenue. Work your way north past every major retailer you’ve ever heard of (Levi’s, Crate & Barrel, Coach) and keep an eye out for the Historic Water Tower, whose limestone frame survived the Great Chicago Fire of 1871 and whose intimate one-room interior makes a remarkable setting for art exhibits today. The nearby Water Tower Place mall is known for affordable price points (tenants include Macy’s and Sports Authority) and the massive, 52,000-square-foot American Girl Place.

A block east of here stands the Museum of Contemporary Art Chicago and within it the MCA Store. Director Mark Millmore sources clever, innovative gifts and goods from all corners of the planet, such as hand-blown Murano glass earrings from Italy ($44) and candles that look like smooth white river stones ($19 for a box of five). Also at the museum: Puck’s café, whose floor-to-ceiling windows and inventive seasonal menu make it a delightful alternative to the crowded lunch spots on Michigan Avenue.

Oak Street marks the end of the Mag Mile—and the beginning of Chicago’s wealthy Gold Coast neighborhood. But don’t put your wallet away just yet. As you follow Oak west toward Rush Street, you’ll find some one-of-a-kind and (relatively) affordable shops. Independence specializes in American-made apparel and goodies for men (selvage-denim aprons for $138, handmade copper flask funnels for $40); Bravco, a decades-old family-run drugstore, has a killer selection of travel-size toiletries in the back: Bumble and Bumble shampoo ($8), American Crew pomade ($11) and more.

By the time you reach Rush Street, you’ll be ready for a massage, a drink or both. Stop at the Waldorf Astoria’s Elysian Spa & Health Club (walk-ins welcome; massages from $160), or continue south and hang a left on Delaware Place to loop back to the Mag Mile—and the bar with the most magnificent view of it: the Signature Lounge at the 96th, on the 96th floor of the John Hancock Center.  It’s two stories higher than the Observatory and charges no admission fee, so you can ogle the vistas at no charge and spend your savings on a “Chicago’s Best” sidecar martini instead ($15).

Lincoln Park
Streets lined with historic town houses, world-famous restaurants and iconic attractions make this north Chicago neighborhood a popular weekend destination for city residents and out-of-towners alike.

Lincoln Park is also known for its trendy-boutique scene on Armitage Avenue and Halsted Street—but the real shopping tour starts in the park itself, where the Saturday morning Green City Market draws nearly 60 vendors and stalls heaped high with heirloom vegetables, sauces, jams and cheeses. Except for the wild-caught fish, all goods hail from within 300 miles of the city. Look for Finnish-style baked Brun-uusto cheese from Brunkow Cheese of Wisconsin ($6) and handcrafted beeswax tea-light candles from Elburn, Illinois’s Heritage Prairie Farm ($1 each).

If it’s a nice day, stroll through the nearby Lincoln Park Zoo on paths that wind past enclosures sheltering kangaroos, tigers, monkeys and other creatures. (Note to parents: Wild Things!, the zoo shop across from the African lion exhibit, has a fine collection of stuffed animals.)

It’s a walk of less than a mile (or a $10 cab ride) from the zoo to the boutiques. Pet lovers can choose from endless patterns and prints when ordering custom collars from Barker & Meowsky—piglets, sailboats or rocket ships?—and sneak a belly rub to the owner’s gregarious chocolate lab, Gus (collars from $12). At Vosges Haut Chocolat, startlingly delicious ingredients, like chili peppers and Taleggio cheese, elevate chocolate truffles from a ho-hum house gift (from $10 for a four-piece box). 1154 Lill Studio invites shoppers to design their own handbags (from $48); the DIY theme continues at Aroma Workshop, whose soft-spoken owner, Tedd Neenan, patiently helps you create your own fragrance from vials of scented oils with names like blood orange, cassis and tea rose (from $14).

At Blues Jean Bar the staff does all the work. You’ll belly up to a weathered wood bar where a “jeantender” asks for your style preference, size and wash (light, medium or dark?), then serves up your best denim match (jeans from $180).

Cap off the day in proper Lincoln Park style with a fine meal and a show. The Italian-themed Balena, which opened less than a year ago, is already the place to be. Its Peter’s Bread selection, named for the restaurant’s baker, has a cult-like following, as do the desserts, by pastry chef Amanda Rockman (the fluffy, angel-food-like tiramisu will change your life). Last stop: a standup show at UP Comedy Club. It’s the new venue at the famous Second City comedy school; you just may catch the next Steve Carell or Tina Fey.

Wicker Park and Bucktown
In the past decade or so, Wicker Park has transformed from a gritty, artsy swath of northwest Chicago to a hipster haven. Among the early pioneers was Milk & Honey Café, a breakfast-and-lunch spot that opened in 2002. Back then, owner Carol Watson found the existing granola options so dissatisfying that she started making her own—and thus Chicago’s best granola was born. You can order a bowl of her original mix, served with vanilla yogurt and fresh fruit ($5.50), or pick up one of the snazzier flavors—pumpkin spice; Rick Bayless’s Mexican Mix—sold by the pound ($7).

A few doors down, the contemporary-cool men’s and women’s clothing boutique Penelope’s brings attention to underrepresented designers. The noteworthy tie selection features fun patterns and prints from Brooklyn-based Hill-Side (from $84) and Chicago’s own DiBi Ties (from $45).

Milwaukee Avenue, one of the main shopping streets in this part of town, is strung with indie hits like the new Lomography Gallery Store, which lures amateur analog photographers. Caza, only slightly older, offers an outstanding selection of women’s vintage apparel—you may find a handmade geisha gown for $34 or a 1940s-era mink cape for $440. Nearby Antique Taco sells antiquey bits and pieces from across the Midwest (mason jars from $8, a vintage railroad apron for $35) alongside its namesake offering: tacos (the crispy fish tempura, $8, is highly recommended).

When you’ve had your fill of tacos, follow Damen Avenue north into Bucktown. The boutiques here tend to be of the more upscale sort (Cynthia Rowley, Alexis Bittar). Must-stops include Psychobaby, where you can design a custom T-shirt—or bib, or pillowcase—for your kid in just 15 minutes (from $14); p.45 for women’s on-trend fashions and accessories by local and national designers; and Virtu, a charming space with a surprising assortment of home goods and other items (ceramic milk-bottle vases for $18; featherweight silk-and-cashmere scarves for $172), plus a huge selection of Snow & Graham letterpress greeting cards ($4 each).

Two more blocks up Damen awaits your last and tastiest stop: Red Door, a cozy new gastropub with a serious locavore side. Its kitchen turns the best ingredients in the Midwest into delectable creations—mushroom quinoa with prunes, crispy kale and Marcona almonds; hanger steak with charred rapini butter and fingerling potato confit. A visit to Red Door will remind you that Chicago, too, can be the capital of fresh.

Magnificent Mile & Gold Coast
Haberdash EDC 611 N. State St.; 312-646-7870;

P.O.S.H. 613 N. State St.; 312-280-1602;

Water Tower Place 835 N. Michigan Ave.; 312-440-3166;

American Girl Place 835 N. Michigan Ave.; 877-247-5223;

MCA Store Museum of Contemporary Art Chicago, 220 E. Chicago Ave.; 312-397-4000;

Independence 47 E. Oak St.; 312-675-2105;

Bravco 43 E. Oak St.; 312-943-4305;

City Gallery Historic Water Tower, 806 N. Michigan Ave.; 312-742-0808;; free admission

Signature Lounge at the 96th John Hancock Center, 875 N. Michigan Ave., 96th fl.; 312-787-9596;

Puck’s Museum of Contemporary Art Chicago, 220 E. Chicago Ave.; 312-397-4034; lunch for two, $46*

Elysian Spa & Health Club Waldorf Astoria Chicago, 11 E. Walton St.; 312-646-1310;

Lincoln Park
Green City Market Lincoln Park; 773-880-1266;; Saturday, 7 a.m. to 1 p.m.

Barker & Meowsky 1003 W. Armitage Ave.; 773-868-0200;

Vosges Haut Chocolat 951 W. Armitage Ave.; 773-296-9866;

1154 Lill Studio 904 W. Armitage Ave.; 773-472-7036;

Aroma Workshop 2050 N. Halsted St.; 773-871-1985;

Blues Jean Bar 2210 N. Halsted St.; 773-248-5326;

Lincoln Park Zoo 2001 N. Clark St.; 312-742-2000;; free admission

UP Comedy Club 230 W. North Ave.; 312-662-4562;

Balena 1633 N. Halsted St.; 312-867-3888; dinner for two, $75

Wicker Park & Bucktown
Penelope’s 1913 W. Division St.; 773-395-2351;

Lomography Gallery Store Chicago 1422 N. Milwaukee Ave.; 872-206-2253;

Caza 1459 N. Milwaukee Ave.; 773-227-7774;

Psychobaby 1630 N. Damen Ave.; 773-772-2815;

p.45 1643 N. Damen Ave.; 773-862-4523;

Virtu 2034 N. Damen Ave.; 773-235-3790;

Milk & Honey Café 1920 W. Division St.; 773-395-9434; breakfast for two, $11

Antique Taco 1360 N. Milwaukee Ave.; 773-687-8697; tacos from $7

Red Door 2118 N. Damen Ave.; 773-697-7221; dinner for two, $70

*Not including drinks, tax or tip.

RCI affiliated resorts near Chicago include:

Silverleaf’s Fox River Resort 4863
On the shore of Fox River, where you can canoe and fish. 2558 N. 3653 Rd., Sheridan, IL
Member Reviews: “If you like quiet, this resort is perfect for you. When you wake up, all you hear is the birds.”
“Chicago is relatively close and has plenty to offer, from baseball games to shopping to the Navy Pier.”
“We drove about 30 minutes from the resort to see the beautiful Chicago area.”

For complete member reviews (as member reviews have been condensed) and additional resort listings, visit or call 800-338-7777 (Weeks) or 877-968-7476 (Points). Club Members, please call your specific Club or RCI telephone number.

Non-RCI affiliated resort:

Wyndham Blake Chicago
A boutique-style hotel near some of Chicago’s best shopping spots. 500 S. Dearborn; 312-986-1234;; doubles from $107 per night

NOTE: Information may have changed since publication. Please confirm key details before planning your trip.

Published: Spring 2013 
Photos: Lincoln Park Zoo; Haberdash
RCI® Subscribing
Search Other Destinations to Suit Your Interests
play eat shop relax explore
See Also...
Web Exclusive: Wisconsin’s Old-time Supper Clubs
September 1, 2012
Learn More
More Destinations
San Diego, CA Park City, UT Vancouver, B.C.
Washington, D.C. Cancún, Mexico
USA Northeast Southeast Florida
Midwest Southwest West Hawaii
Africa Asia Australia Canada
Mexico Caribbean Central/South America
Europe Cruise
Browse All Destinations
  • Advertisement
    By clicking on the ad below, you will be directed to a website not operated by RCI and you agree to be subject to the terms and conditions and privacy policy of that third party website.