Chicago features stellar shopping for every style and budget. Whether your group is looking for high-end designers or one-of-a-kind crafts, Chicago has a shopping district or event where shoppers can find great fashion-forward pieces.Our Chicago shopping guide features full and half-day excursions to customize the experience for your clients. Mix and match the itinerary options below to include downtown shopping, outlet malls or neighborhood retail districts.
FULL DAY: DOWNTOWN SHOPPING
Morning – The Magnificent Mile
- Water Tower Place (835 N. Michigan Ave.)
- The Shops at North Bridge (520 N. Michigan Ave.)
- 900 North Michigan Shops (900 N. Michigan Ave.)
For a shopping experience that's as diverse as Chicago itself, head to The Magnificent Mile. This stretch of Michigan Avenue offers shoppers an abundance of retail options, including towering shopping centers, chic designer studios and trendy favorites. Groups will find lavish stores such as Gucci, nestled next to national chains such as Gap and Ralph Lauren.
Chicago's weather may not always be conducive to street shopping, but the Magnificent Mile has visitors covered – literally – with three indoor malls that let people shop in comfort. The Shops at North Bridge offers seven city blocks of shopping, while Water Tower Place is home to American Girl Place and The LEGO® Store. Finally, the 900 North Michigan Shops feature dozens of great stores, from Lululemon Athletics to Atlas Galleries. For special offers and shopping incentives, guests can simply visit the concierge desk at each mall.
Apart from the immaculate shopping, The Magnificent Mile also features renowned attractions, such as the famous Water Tower and Pumping Station, and exquisite restaurants for groups to enjoy once they've had their shopping fix.
Afternoon – The Loop/State Street
- Macy's on State Street (111 N. State St.)
- Block 37 (108 N. State St.)
- Garrett Popcorn (27 W. Jackson Blvd.)
The portion of State Street that runs from Lake to Jackson is known as the shopping district of the loop and has dozens of stores to explore, from H&M and Old Navy to DSW and Nordstrom Rack. For a true Chicago staple, make a stop at Garrett Popcorn for a bag – or tin – of handmade popcorn. Try the sweet-and-salty Chicago mix, with caramel and cheddar cheese popcorn.
The shopping district also has its own indoor mall at Block 37, where you can find a mix of retail and dining options in the five-story building. Peruse the racks at retailers like Anthropologie and Eileen Fisher, and indulge in sweet treats at Godiva Chocolatier and Magnolia Bakery.
Across the street, visitors will find the famous Macy's on State Street, the world's second-largest department store. Be sure to admire the buildings stunning architecture: granite pillars, century-old clocks, a three-tiered Burnham fountain and a Tiffany Favrile glass ceiling. Stop by the visitor desk for a guided tour of the iconic department store. You can also pick up a Macy's visitor passes for your group, which offers up to 10% savings in all Macy's stores.
FULL DAY: OUTLET MALL SHOPPING
Option #1 – Fashion Outlets of Chicago (5220 Fashion Outlet Way, Rosemont, IL)
The Chicago shopping adventure extends beyond the luxury stores of downtown. Deal-seekers can head outside the city to the Fashion Outlets of Chicago, the newest shopping experience in Chicagoland. The mall features a plethora of stores, from Calvin Klein and Burberry to Nike Factory and Calypso St. Barth, offering brand-name items marked down from retail. Groups can hop the shuttle at The Shops at North Bridge on Michigan Avenue and head out to Rosemont for a day of shopping bliss. There is also free motorcoach parking for those groups with their own transportation.
Option #2 – Chicago Premium Outlets (1650 Premium Outlets Blvd., Aurora, IL)
Another great outing is the Chicago Premium Outlets in Aurora, just 40 miles west of Chicago. This shopping mecca offers an impressive collection of designer and brand-name stores, including MaxMara, J. Crew and Kate Spade New York. This outdoor mall is perfect for a day of retail therapy, and its abundance of in-store deals make it a bargain hunter's paradise. Make sure to check out the recent additions as part of its multi-million dollar expansion, which includes more shopping, dining and parking, as well as group-friendly options such as a state-of-the-art Guest Services center, tour bus parking and a bus drop-off plaza, as well as VIP amenities for pre-registered tour groups.
HALF DAY: NEIGHBORHOODS SHOPPING
Option #1 – Wicker Park/Bucktown
The bohemian west-side neighborhoods of Wicker Park/Bucktown provide shoppers with a completely different flare than the bustling streets of downtown. Stores lining Damen, North and Milwaukee avenues range from big-name designers like Marc Jacobs and Nanette Lepore to small boutiques selling vintage clothing and locally made jewels and art. You can even find a number of antique shops and music stores, including Reckless Records, selling new and used vinyl, CDs and more.
Option #2 – Lincoln Park
In Lincoln Park, Armitage Avenue and Halsted Street are known for their charm and plentiful selection of fashionable stores. The historical architecture along Armitage provides shoppers with pleasant scenery as they hop from store to store. The area includes a number of brand names, from Francesca's to Bebe. You can also find a variety of boutiques like Comfort Me and Art Effect, which sell fun and unique items.
Markets and Fairs
Street fairs are big in Chicago. Year-round festivals take place all over the city, featuring unique trinkets, locally made clothes and jewelry and cultural souvenirs.
Groups can uncover one-of-a-kind designs from talented DIY-ers at many Chicago craft fairs. The Renegade Craft Fair (Dec. 5-6), housed in the Bridgeport Arts Center, features hundreds of vendors selling everything from cutting-edge fashion and jewelry to sophisticated ceramics and contemporary furniture. Or send guests over to the West Loop for the Randolph Street Market, a monthly event stocked with vintage treasures, art, fashion, antiques and more.
In Chicago's Andersonville neighborhood, Late Night Andersonville (Dec. 4) is special shopping event when local shops and restaurants feature extended hours, exclusive deals and more, while Swedish American festival Julmarknad (Dec. 5-6) features traditional handicrafts and free performances.
Discover even more group-friendly shopping in Chicago.