Chicago is one of America's premier shopping destinations, offering an impressive blend of upscale department stores, charming boutiques, and distinctive shopping districts. Whether you're hunting for designer labels, vintage treasures, or locally crafted goods, the Windy City delivers exceptional shopping experiences for every taste and budget.
From the glittering storefronts along Michigan Avenue to the character-filled shops of neighborhood districts, this guide highlights the best shopping in Chicago for visitors and locals alike.
The Magnificent Mile
The Magnificent Mile, a stretch of North Michigan Avenue from the Chicago River to Oak Street, represents the pinnacle of shopping in Chicago. This world-renowned shopping district features more than 460 retailers across eight city blocks, including flagship department stores, luxury boutiques, and popular brands.
The district also houses multiple shopping centers, including Water Tower Place and The Shops at North Bridge, making it a one-stop destination for fashion enthusiasts.
Beyond retail therapy, the area offers stunning architecture and public art installations that create an unmatched shopping atmosphere. While exploring this shopping mecca, don't miss the historic Water Tower, which survived the Great Chicago Fire of 1871 and stands as a beloved city landmark.
Oak Street and Streeterville
Just steps from the northern end of the Magnificent Mile, Oak Street presents Chicago's most exclusive shopping experience. This refined shopping district features high-end international designers like Prada, Hermès, and Van Cleef & Arpels in charming, historic buildings along a tree-lined street. The intimate environment offers a welcome contrast to the busy Magnificent Mile, with more personalized service.
Nearby Streeterville extends these upscale options with specialty retailers and service-oriented businesses. Nestled between Michigan Avenue and Lake Michigan, this neighborhood provides convenient access to both shopping destinations and cultural attractions, making it an excellent base for exploring the best shopping in Chicago.
Boutiques in Wicker Park and Andersonville
Chicago's neighborhood shopping districts offer treasure troves of independent retailers showcasing local designers, vintage finds, and artisanal goods that you won't find anywhere else.
Wicker Park has transformed from an artistic enclave to one of Chicago's trendiest neighborhoods. The area retains its creative spirit through distinctive boutiques like Vintage Underground, offering curated vintage jewelry and accessories, and Kokorokoko, specializing in '80s and '90s vintage fashion. For contemporary styles from emerging designers, Una Mae's provides carefully selected clothing and accessories with an emphasis on sustainable and ethical production.
Andersonville delights shoppers with its independent spirit and diverse selection of locally owned shops. Browse through Women and Children First, one of the largest feminist bookstores in the country, or discover Scandinavian gifts and goods at Svea. The neighborhood's commercial corridor along Clark Street features numerous antique shops, home décor stores, and specialty food retailers, making it perfect for finding unique souvenirs and gifts.
Lincoln Park and Lakeview
These neighboring North Side communities offer excellent shopping in a residential setting. Lincoln Park blends national retailers with local boutiques along its commercial streets, particularly Armitage Avenue and Halsted Street. Shoppers can discover clothing from independent designers at boutiques like Art Effect, which also features jewelry, gifts, and home accessories.
Lakeview, especially the Southport Corridor, has evolved into a premier shopping destination with both local boutiques and recognized brands. Shops like Tilly and Krista K offer fashionable women's clothing and personalized service. The area's relaxed, tree-lined streets create an enjoyable atmosphere for exploring diverse shopping options ranging from apparel and accessories to home goods and specialty foods.
900 North Michigan Shops
This vertical shopping center anchors the northern end of the Magnificent Mile with seven levels of exceptional shopping. The 900 North Michigan Shops represent the best shopping mall in Chicago for luxury experiences, housing approximately 70 retailers in an elegant, light-filled atrium.
Anchored by Bloomingdale's, this upscale center features prestigious brands like Gucci, MaxMara, and J.Crew, while the Luxury on Seven area showcases fine jewelry and personal shopping services. Recent renovations have introduced a contemporary food hall with gourmet options from local chefs. Its prime location and sophisticated atmosphere make it easy to incorporate into a day of shopping in Chicago, particularly when exploring the northern section of the Magnificent Mile.
Art Meets Retail in River North
River North's reputation as Chicago's gallery district extends to its distinctive shopping scene, where art and retail merge seamlessly. This neighborhood, just west of the Magnificent Mile, offers unique shopping opportunities within walking distance of major attractions.
The Merchandise Mart houses design showrooms and retail spaces focused on home furnishings and interior design. Though primarily serving professionals, many showrooms welcome the public, making it ideal for home décor enthusiasts.
Throughout River North, independent retailers showcase artisan-made goods, designer furnishings, and distinctive fashion.
Local Shopping Spots in Chicago
Beyond the major districts, Chicago abounds with neighborhood shopping gems. The Loop offers excellent shopping along State Street, including Macy's in the historic Marshall Field's building with its magnificent Tiffany ceiling.
Chicago's diverse neighborhoods each provide distinctive shopping experiences reflecting their unique character. Pilsen showcases Latino culture through colorful shops and street art, while Chinatown offers authentic Asian goods.
For market enthusiasts, the Maxwell Street Market operates Sundays year-round, featuring a mix of merchandise, street food, and live music that's been a Chicago tradition since 1912.
Food and Drink Breaks
Shopping in Chicago requires strategic refreshment stops to maintain energy. Along the Magnificent Mile, sophisticated tea at The Drake Hotel offers a refined respite. For quick energy boosts, specialty coffee shops like Intelligentsia and Dollop Coffee provide quality beverages throughout the city's shopping districts.
Many department stores and malls feature excellent dining options. The Walnut Room in Macy's State Street continues a dining tradition dating back to 1907, while Eataly Chicago in River North combines Italian marketplace shopping with multiple dining venues.
What To Do Nearby With CityPASS® Tickets
After indulging in Chicago's extraordinary shopping opportunities, explore the city's remarkable attractions with Chicago CityPASS® tickets. These tickets provide access to iconic attractions like Shedd Aquarium, Skydeck Chicago, Shoreline Sightseeing Architecture River Tour, and the Field Museum, many conveniently located near shopping districts.
Ready to experience the best of Chicago's shopping and attractions? Purchase your Chicago CityPASS® tickets today and save on admission to Chicago's top things to do while you explore its world-class shopping districts.
Chicago Lodging
To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you: