Chicago Shopping Guide
From luxury boutiques to indie markets—discover the best retail destinations in the Windy City
Retail Paradise
Chicago offers one of the most diverse shopping experiences in America—from the luxury flagships of the Magnificent Mile to vintage treasures in Wicker Park. With no sales tax on clothing, it's a shopper's dream destination.
Stores on Magnificent Mile
Tax on Clothing
Independent Bookstores
Chicago's Top Shopping Destinations
Explore these iconic retail corridors and hidden gem neighborhoods
The Magnificent Mile
Chicago's most famous shopping stretch features flagship stores like Nike Chicago, luxury brands (Tiffany, Gucci), and the historic Water Tower Place mall.
Must-Visit Stores:
- • 900 North Michigan Shops
- • Apple Michigan Avenue
- • Eataly Chicago
- • The Shops at North Bridge
Wicker Park & Bucktown
Hipster haven with indie boutiques, vintage shops, and local designers along Milwaukee Ave and Damen Ave.
Hidden Gems:
- • Una Mae's - Trendsetting boutique with emerging designers
- • Kokorokoko - Vintage clothing curated by local stylists
- • RR#1 - Chicago-made home goods and gifts
Andersonville
Charming neighborhood with women-owned businesses, Scandinavian shops, and the famous Woolly Mammoth antique store.
BEST FOR
Unique gifts & home decor
MUST VISIT
Women & Children First bookstore
Iconic Chicago Malls
Water Tower Place
Historic 8-story mall on Michigan Avenue with 100+ stores including American Girl Place and Macy's.
LOCATION
Magnificent Mile
The Shops at North Bridge
Luxury shopping destination with Nordstrom, Anthropologie, and premium brands.
LOCATION
River North
Roosevelt Collection
South Loop shopping center with Target, Alamo Drafthouse Cinema, and local boutiques.
LOCATION
South Loop
Seasonal Shopping Experiences
Christkindlmarket
German Holiday Market | November-December
Authentic European holiday market with handcrafted ornaments, woolens, and glühwein.
Daley Plaza
Randolph Street Market
Vintage & Antiques | Monthly May-December
150+ vendors selling vintage clothing, mid-century furniture, and collectibles.
West Loop
Chicago Shopping Tips
Smart Shopping
- Take advantage of no sales tax on clothing in Chicago
- Many stores offer student discounts with ID
- Check for city passes that include shopping discounts
- Visit during January and July for best seasonal sales
Getting Around
- Use the L train to reach most shopping districts
- Downtown has pedestrian tunnels connecting stores in winter
- Consider Divvy bikes for neighborhood hopping
- Many hotels offer shopping shuttle services
Ready to Shop Chicago?
Get our exclusive Chicago Shopping Pass with discounts at 100+ stores and insider tips.
