Chicago has a reputation for its iconic architecture, deep-dish pizza, and lively neighborhoods, but it’s also a fantastic city for shopping and exploring markets. Whether you’re hunting for designer bargains, discovering local fashion, or sampling sweet treats from top bakeries, Chicago offers a variety of tours catering to different interests. Our favorites include a donut adventure through the West Loop, private outlet shopping trips, and a street art tour that highlights Chicago’s creative side. These experiences give you a chance to see the city beyond the usual tourist spots while indulging in some retail therapy.
If you’re into food, the Fulton Market Delicious Donut Adventure is a must—sampling donuts from four of Chicago’s best bakeries while wandering a neighborhood packed with culinary innovation. For those craving retail therapy, private shopping tours to Chicago Premium Outlets or Fashion Outlets of Chicago deliver big savings on luxury brands. And if street art is your thing, the Offbeat Fulton Market Graffiti and Murals Tour offers a fresh perspective on Chicago’s creative scene. Below, you’ll find detailed descriptions of each tour to help you plan your perfect shopping and market experience.
1. Fulton Market Delicious Donut Adventure and Walking Food Tour
Rating: 5.0/5 (32 reviews)
Price: $65.00 per person
Duration: 1 hour 30 minutes to 2 hours
Location: Chicago, USA
If you’re craving sweet indulgence, this donut-focused walking tour is hard to beat. Starting at the Chicago French Market, you’ll visit four top bakeries and sample donuts representing diverse culinary traditions. Every stop offers a different flavor profile, from classic glazed to creative Japanese-inspired treats. The tour wanders through the West Loop and Restaurant Row, two neighborhoods celebrated for their vibrant food scenes. Along the way, your guide shares insights into Chicago’s culinary culture, making this more than just a sugar rush—it’s a taste of the city’s foodie heart.
What makes this tour stand out is its balance of walking and tasting, making it perfect for those who want a sweet break from sightseeing. The stops include Do-Rite Donuts (famous for their rotating flavors and fried chicken sandwich), the innovative Voodoo Doughnut, and Sawada Coffee, where you can enjoy doughnuts paired with Japanese coffee artistry. The price is reasonable for four donut tastings and a guided walk in a lively neighborhood filled with eateries and artisan shops.
Bottom Line: If you love doughnuts and want to explore Chicago’s culinary neighborhoods, this tour offers a delicious and relaxed experience that’s easy to fit into any day.
2. Outdoor Escape Room in Chicago – Fulton Market
Rating: 5.0/5 (23 reviews)
Price: $75.00 per group (up to 6)
Duration: About 2 hours
Location: Chicago, USA
For something a little different, this outdoor escape room combines puzzle-solving with a neighborhood stroll. It’s a hybrid of scavenger hunt, escape room, and urban adventure, designed to immerse you in the vibrant Fulton Market area. Your team searches for clues hidden in murals, statues, and landmarks, cracking codes along the way using an app that guides your progress.
What makes this experience special is its interactive nature. It’s perfect for groups or families who want to combine sightseeing with a challenge that keeps everyone engaged. The clues are integrated into the neighborhood’s art, architecture, and street scenes, so you get to see Chicago’s dynamic arts scene firsthand. Since it’s designed as a group activity, it’s an excellent choice for friends or corporate outings.
Bottom Line: If you enjoy puzzles and exploring Chicago in a playful way, this outdoor escape room delivers a memorable city adventure with a twist.
3. Offbeat Fulton Market Graffiti and Murals Street Art Tour
Rating: 5.0/5 (1 review)
Price: $40.00 per person
Duration: About 2 hours
Location: Chicago, USA
This tour is a true celebration of Chicago’s street art scene, an aspect often overlooked amidst the city’s skyscrapers and museums. Walking along the Union Pacific viaduct and through Fulton Market, you’ll see murals and graffiti from artists around the world. Your guide explains the history of these works, which started as a community project and grew into an international attraction.
What makes this tour compelling is its focus on urban art as a form of cultural expression. It’s ideal for travelers interested in contemporary art, social commentary, or just discovering a different side of Chicago. The tour ends in Fulton Market’s lively dining and drinking spots, perfect for relaxing after your walk.
Keep in mind, with only one review, it’s a niche experience, but highly rated for authenticity and insight. If you want to experience Chicago’s street art firsthand, this is your chance.
Bottom Line: Perfect for art lovers or those curious about city culture, this tour reveals Chicago’s creative street art scene through engaging storytelling.
$40.00 per person
4. Chicago Local Fashion Designers Shopping Tour with a Stylist
Rating: No reviews yet
Price: $150.37 per person
Duration: About 3 hours
Location: Chicago, USA
Fashion-savvy travelers will appreciate this personalized shopping experience guided by a professional stylist. Starting in Roscoe Village, your stylist performs a mini style consultation to understand your preferences. From there, the tour visits boutique shops and local designer studios in Lincoln Park and Wicker Park, helping you discover unique pieces that reflect Chicago’s fashion scene.
What makes this tour stand out is its tailored approach. The stylist assists with styling tips, pulls pieces for you to try, and offers advice on how to incorporate local fashion into your wardrobe. It’s more than just shopping—it’s a mini fashion class designed to boost your confidence and update your style.
While it’s pricier than other tours, the value lies in one-on-one guidance and access to Chicago’s independent designers. It’s ideal for style-conscious travelers wanting a curated, boutique shopping experience.
Bottom Line: If you’re interested in fashion and personalized styling, this tour offers a hands-on way to explore Chicago’s local designers.
$150.37 per person
5. Private Shopping Tour from Chicago to Chicago Premium Outlets
Rating: No reviews yet
Price: $295.85 per person
Duration: 5-6 hours
Location: Chicago, USA
This private tour takes you directly from your hotel to Chicago Premium Outlets, a sprawling outdoor shopping center with over 170 stores including Coach, Nike, and Saks Fifth Avenue Off Fifth. The tour begins with a pickup at your accommodation, then a comfortable drive to the outlets. You’ll have around four hours to browse at your own pace, taking advantage of significant discounts on designer brands.
What sets this tour apart is its private, door-to-door convenience, making it ideal for those who want maximum flexibility. The outlet shopping experience is designed to be relaxed and private, with plenty of options for lunch or coffee at the mall’s cafes. It’s perfect if you’re after serious savings and a tailored shopping day.
Bottom Line: Best suited for serious shoppers, this tour offers a hassle-free day of bargain hunting at one of Chicago’s premier outlet malls.
$295.85 per person
6. Private Shopping Tour from Chicago to Fashion Outlets of Chicago
Rating: No reviews yet
Price: $260.28 per person
Duration: About 5 hours
Location: Chicago, USA
Similar to the previous, this private tour takes you from Chicago to Fashion Outlets of Chicago, just minutes from O’Hare Airport. With over 130 designer brands like Gucci, Prada, and Versace, this mall offers a luxury shopping experience at outlet prices. You get around four hours to explore and find deals on high-end fashion and accessories.
This tour’s advantage is its focus on luxury brands and the convenience of door-to-door service. It’s perfect for travelers who want to combine shopping with comfort, especially those pressed for time or seeking a more exclusive experience.
Bottom Line: For upscale bargain-hunters, this tour provides a premium outlet shopping experience with personalized transport.
$260.28 per person
7. Private Shopping Tour from Chicago to Lighthouse Place Outlets
Rating: No reviews yet
Price: $377.23 per person
Duration: 6-7 hours
Location: Chicago, USA
Finally, the trip to Lighthouse Place Outlets in Indiana offers a full-day shopping experience. With over 75 stores, including Michael Kors, Vera Bradley, and Columbia Sportswear, you’ll enjoy a variety of brands in a scenic outdoor setting. The tour includes a comfortable drive from your hotel and about four hours to browse, with time to enjoy local cafes and eateries.
This is the most extensive of our outlet options, ideal for dedicated shoppers who want to maximize their time and shopping opportunities. The longer duration allows for a more relaxed pace and exploring beyond just the stores.
Bottom Line: If you’re serious about outlet shopping and don’t mind a longer day, this tour offers a comprehensive experience with plenty of retail choices.
$377.23 per person
How to Choose Your Chicago Shopping & Market Tour
Picking the right experience depends on your interests, budget, and how much time you want to dedicate. If you love sweet treats, the Fulton Market Delicious Donut Adventure offers a tasty neighborhood walk. For fashion lovers, the personalized stylist tour provides expert guidance through local boutiques. Budget travelers should consider the street art tour, which combines urban exploration with artistic discovery. Shoppers seeking big savings will find value in the private outlet tours to Chicago Premium Outlets or Fashion Outlets of Chicago.
Consider your physical activity level—some tours involve walking, while others are private and chauffeur-driven. Booking early is recommended, especially for the popular outlet trips, to ensure availability during peak shopping seasons or holiday sales.
Final Thoughts
Chicago’s diverse shopping scene can keep any shopper busy. For a quick, sweet fix, the donut tour is perfect. If you want to explore street art, the murals tour will surprise you. Serious shoppers will love the private outlet trips, especially when combined with discounts on designer brands. For a more curated fashion experience, the stylist-led shopping tour adds personalized flair.
Whatever your interests, there’s a Chicago shopping or market tour waiting for you. Planning ahead and booking early guarantees a smoother, more enjoyable experience—so pick your favorite and get ready to shop till you drop in the Windy City.