Chicago in a Day: Food and Architecture Private Walking Tour
Recommended by 100% of travelers
Badge of Excellence
Chicago, USA
- 5 hours (approx.)
- Group discounts
- Mobile ticket
- Offered in: English
Overview
Discover the best of the Windy City’s architectural highlights—and then move on to a tasting tour of its culinary standouts—on this half-day, small-group tour. Pick between morning and afternoon start times, meet your guide at the Chicago Theatre, and set off to discover highlights like the Riverwalk, John Hancock Building, and more. Then, indulge in tastings of everything from deep-dish pizza to hot dogs.
- This small-group tour is capped at 12 to keep things personal
- Discover Chicago’s top landmarks and dishes on this two-in-one tour
- Enjoy enough tastings and bites to add up to a generous lunch
- Learn the stories behind Chicago’s top architectural landmarks
What's Included
Meeting and Pickup
Itinerary
Additional Info
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos





Reviews
5.0
based on 54 reviews
Mike_B, Sep 2023
“Chicago Dave” was our guide and he did a great job of conveying his love for and knowledge of Chicago to the tour group.
He had fun and informative stories and “brought to life” many of the places that we stopped at during the tour!
Kathleen_W, Aug 2023
Our tour guide DAsh was excellent…so knowledgeable and keen to share all his information…. Even though walking in 40 degrees…he made it a memorable event and as pleasant as possible with the heat.. learnt so many fascinating aspects of chicago
Nyla_S, Aug 2023
Our tour was good if your into architecture. A lot of walking so wear comfy shoes. Richard was very informative and if he didn't know something he made sure to find out. The food he took is to was ALL DELICIOUS! Overall good day.
RSCODY, Jun 2023
I especially enjoyed seeing the Sullivan and Marquette Buildings. Rich, our tour guide, was very knowledgeable and shared lots of interesting history and stories with us (really liked hearing about the Jewelry Building).
The food tour stops were also great and I finally got to experience a real Chicago hot dog (thank-you Rich).
Montiquelyn_D, May 2023
Excellent experience, great tour guide, very enthusiastic about the history of Chicago, he answered all questions!
ABJ_Z, Mar 2023
Dash our tour guide was enthusiastic and very knowledgeable about his home City. This made the tour very enjoyable despite a temperature of -10 degrees. Dash showed us various different buildings from different phases of Chicago's history. I really enjoyed the ride on the Loop.
John_R, Mar 2023
I thought this tour was fantastic. Our guide Dash was hands down the best tour guide I've ever had. He filled the 3 hour architecture part of tour with a bunch of wonderful spots and was extremely knowledgeable of every aspect of all of them. I felt like he could have easily done another 3 hours just on architecture. I was exactly blown away by the food but that has zero reflection upon the tour and more me being a picky eater. The hotdog was my favorite of the 3 but I had to eliminate a few of the toppings that weren't to my liking. The beef sandwich had potential but next time I order it will be sans spice lol. The pizza was most disappointing to me. Again, I'm an extremely picky eater, adjustments had to be made but the sausage had already seeped into the flavor of my slice lmao. All joking aside I would highly recommend this tour and if you're lucky you will have Dash as your guide. Enjoy the tour, I did.
Brian_S, Oct 2022
David was a superb tour guide, full of information and history. He was not only personable, but he also was able to personalize the trip for each participant.
Marvetta_B, Sep 2022
Our tour guide was Chicago Dave . We had a wonderful time touring with him . We went to there different eating places all was excellent . History and architecture was really beautiful. Recommend this tour . Wear comfortable shoes a lot of walking . Thank you Chicago Dave
(OG)
Glenda_S, Aug 2022
Dash was an awesome tour guide! It was like hanging out with a close friend who kept telling you about the history of buildings and Chicago and you're amazed he knows all these stuff lol. It was truly an enjoyable trip and a wonderful introduction to classic Chicago food.
Shane_G, Aug 2022
The tour was great! Lots to see & do. Our tour guide Laura was amazing & very knowledgeable on the sites.
Grace_H, Aug 2022
Chi-Tall Dave is an amazing tour guide. He gave us insight on Chicago then and now. The food stops were delicious and architecture locations were beautiful. Worth it and can’t wait to come back and try all these stops with family and more friends.
juliepsf, Jul 2022
The tour guide, Lara, was excellent. She has a "tour guide personality" and puts 100% into the tour! She is from Chicago and was very informative about the city, past and present. She took us to great food spots. It was a rainy day and she was very creative in minimizing the effects of the weather.
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