Chicago Walking Tour: History & Cuisine

Embark on an epic Chicago day tour with a local guide. Explore the city’s architecture, indulge in delicious local treats, and soak in stunning river views.

Duration: 4 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • The Chicago Theatre - Start the journey beneath the iconic Chicago Theatre marquee, renowned from films, before venturing into the vibrant city streets.
  • Chicago Pedway - If the weather allows, explore the Chicago Pedway, a series of underground tunnels frequented by locals and commuters, especially during winter.
  • **City of Chicago - City…
What's Included
  • Hear stories of Chicago’s past — from Prohibition to the Great Fire and immigrant history
  • Explore top sights & hidden gems — Riverwalk, Magnificent Mile, Pedway, Wrigley Building
  • Taste Chicago’s iconic eats — deep-dish pizza, hot dog, Italian beef & more included
  • Led by expert local guides — passionate storytelling from true Chicago insiders
    -…
What's Not Included
  • Gratuity
  • Drinks and additional food
Additional Information

Explore Chicago’s fascinating history and lively food culture on this engaging walking tour. Experience the city’s renowned architecture and the allure of the Prohibition era while enjoying delicious local dishes. From deep-dish pizza to hidden treasures, relish the tastes of Chicago as an expert guide reveals the city’s culinary delights and intriguing…

Location
The Chicago Theatre
North State Street
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(1166 Ratings)
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Jessica
Mar 13, 2026
Must do in Chicago! - We had such a great time on our tour with Dash! Learning about the history of Chicago, the architecture and close up views inside historical buildings was fascinating. Dash made the tour so interesting! His enthusiasm was contagious, and he was extremely knowledgeable. We highly recommend this tour!!
Review provided by Tripadvisor
Ashleigh_g
Mar 13, 2026
Best tour ever - Rich was an amazing tour guide. This was my first solo trip and I was nervous. I learned a lot about the cool history of Chicago. He kept the entire tour entertaining even though I was the only tourist. He made my solo stay 10x more comfortable. Thank you so much!
Review provided by Viator
G858trmh
Mar 12, 2026
A great experience! - This was such a great experience!! It was just me and Dash for the tour but he did not disappoint. Dash had so much knowledge of the city. There was so much beautiful architecture and so many interesting facts I had no idea about! Food was EXTRA tasty!!! 😋 Definitely recommend this tour. Thanks for a great time!! Oh! I also got to do my first train ride!! So awesome! 🤩
Review provided by Tripadvisor
Betelham_g
Mar 9, 2026
Excellent - It wasn’t rushed, good pace, knowledgeable guide and very friendly. The small group made it manageable.
Review provided by Viator
Seanbk3147tg
Mar 8, 2026
A fabulous way to see and experience true Chicago - Dave was extremely knowledgeable about the city- knew all the architecture and great, genuine places in Chicago which typifies the cultural food.
Review provided by Tripadvisor
Megin_y
Feb 26, 2026
Chicago city tour & food tour - I've booked on Viator couple of times. Tour guide was very good. Informative, helpful and knowledgeable about the city of Chicago. At the end of the tour, he asked us what direction we were heading and helped us get on the public transportation without any problems.
Review provided by Viator
Saira_t
Feb 21, 2026
Chicago in 4.5 hours. - Our guide Dash was amazing. He had a lot of information about the history and was sharing it with a lot of enthusiasm. If and when I return I would love to use this service again. Also met some nice people on this tour which is always a bonus.
Review provided by Viator
Nikola
Feb 19, 2026
Fantasric taste of Chicago - Had a wonderful half day tour with Rich, taking in all the interesting information about Chicago, and its history, also finding out the origins and trying the original chocolate brownie, followed by the tastes of Chicago, and now that i know what a real deep dish pizza is, I may be converted, in my thoughts, if in Chigago again, that is a definite repeat 🤤
Review provided by Tripadvisor
Maureen_j
Feb 16, 2026
This was a fun and... - This was a fun and informative walking tour in Chicago. It’s a lot of walking, so be sure to wear comfortable shoes. Also, the food at the food stop spots could easily be customized to be vegetarian (Portillo’s even makes a veggie Chicago style hotdog!)
Review provided by Viator
Dimitri_p
Feb 16, 2026
It's a good way to... - It's a good way to explore the city in a group setting with a guide. I enjoyed the food, but if you have a sensitive stomach like me just take a bite of each.
Review provided by Viator
From $101
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).