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
(1145 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Minjeong_s
Dec 16, 2025
Highly recommended! I was... - Highly recommended! I was able to experience Chicago’s architecture and food culture overall. Rich was very friendly and provided lots of interesting information.
Review provided by Viator
Matt_g
Dec 13, 2025
Happy I Went On This Tour - Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.
Review provided by Viator
Joycesa2212hd
Dec 8, 2025
Highly recommend - We had an amazing experience with Dash as our guide in Chicago. He was wonderful—friendly, engaging, and incredibly knowledgeable. He showed us all the architecture highlights and shared so much interesting history about the city. We learned a ton and had a great time along the way. I would highly recommend Dash to anyone visiting Chicago or wanting to explore the city more deeply. He truly made the tour special!
Review provided by Tripadvisor
Shawnbeirne
Dec 6, 2025
Best way to see Chicago - This was honestly one of the best tours I’ve ever been on! Rich was REALLY knowledgeable & the flow was great! We saw (& ate) so much more than I expected. It was a truly FUN day!
Review provided by Tripadvisor
Wanderer0117
Dec 6, 2025
Great Day all around! - This was such a great tour. Rich was a wealth of knowledge and took us to the best spots around the city… we Loved the info on the architecture around the loop and the food was the best! Top notch
Review provided by Tripadvisor
Venture64364547941
Nov 29, 2025
Fun and informative, great tour guide. Even though it was a winter storm warning, we had a great time!!!!!!!!!! - Had a great time in the middle of a snowstorm, exploring the city. Our tour guide was knowledgeable and fun at the same time. What a great experience. Dash did an amazing job!
Review provided by Tripadvisor
Elisedeguillaume
Nov 25, 2025
Bery knowledgeable, enthusiastic and sensitive to group needs - Dash was phenomenal, so knowledgeable and enthusiastic. What a delightful half day we spent with him. He was very aware of any pacing needs and attentive to tour members in just the right way.
Review provided by Tripadvisor
Jennifer_e
Nov 24, 2025
Start your Chicago experience with this tour - Dash was fantastic! He loves the City and showed us hidden treasures I’d never seen after traveling to Chicago for nearly 25 years. He pointed us to a list of his favorite off the beaten track finds, so I’d say START your stay in Chicago with this tour. You will NOT be disappointed. He took into account food needs for all. Also, I was having some medical issues I didn’t know about. It resulted in me struggling with the stairs and uphills more than usual. Appreciated that he keyed in and could see I was having some challenges and worked around them, without making a deal of it. Great guide!!!! Great tour!
Review provided by Viator
Sightseer49758810992
Nov 23, 2025
Fantastic tour - Dash was AWESOME. He was incredibly knowledgeable and picked great places. We had so much fun walking around the city and learning. Thanks so much for an amazing tour!
Review provided by Tripadvisor
Chris44591
Nov 19, 2025
Highly recommended! - The 4.5 hours with Rich were exciting and entertaining from start to finish. Rich knows a lot to tell and has answered all the questions. The tour through Chicago's culinary highlights is 100% recommended to every European!
Review provided by Tripadvisor
From $97
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).