Chicago in a Day: Food, History & Architecture Walking Tour
Overview
Available languages
4 hours 30 minutes
Mobile ticket
Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago as a knowledgeable guide unveils the city's culinary secrets and fascinating history.
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
Suitable for all physical fitness levels
This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.
Suitable for all ages and fitness levels, but please note that this tour covers between 4.8 to 6.4 km (3-4 miles) of walking.
We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.
Experiences happen rain, shine, or snow. Please dress accordingly.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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
Enjoy a personal, relaxed, and interactive experience - Small group size (max 12)
Travel for good — run by a certified B Corp committed to ethical, responsible tourism
Visit Millennium Park & The Bean — snap pics at Chicago’s most famous modern landmark
Gratuity
Drinks and additional food
What To Expect
The Chicago Theatre
We begin under the dazzling Chicago Theater marquee, famous from movies, before diving into the lively streets of the city.
Chicago Pedway
Weather permitting, we'll explore the Chicago Pedway, a network of underground tunnels used daily by locals and commuters, especially in winter.
Options
Small Group Chicago in a Day
Private Chicago in Day
Reviews
1,131 reviews
Total reviews and rating from Viator & Tripadvisor
Fabulous Tour!!
A5774WCshannonw,
Nov 4, 2025
- Review from Tripadvisor
5.00Rich was an excellent and knowledgeable guide. Beautiful architecture and so much food. I highly recommend this tour as a great way to see Chicago highlights.
Fabulous way to get a taste of Chicago!
K7790WHalexandras,
Nov 4, 2025
- Review from Tripadvisor
5.00A great way to spend our first day in Chicago. A fabulous guide - Dave. He not only gave us an excellent tour but took into consideration our interests and tailored according. Thank you.
Great Chicago experience!
kylejZ8162KY,
Nov 3, 2025
- Review from Tripadvisor
5.00Very enjoyable! Rich had a lot of interesting stories and history to share. It was a great way to see a lot of Chicago and sample some delicious food in just a few hours.
Go for the tour. Stay for the dogs.
V3249FGjeffh,
Nov 2, 2025
- Review from Tripadvisor
5.00Dave provided us with an interesting and entertaining tour of the city. His extensive knowledge and energetic enthusiasm created a very memorable experience!
Architecture and Food Tour
Doane B,
Oct 30, 2025
- Review from Viator
5.00Love seeing the sites and hearing about the history. The Cultural Center was amazing! Food tours was wonderful. A taste of all their specialties in Chicago! Popcorn, Deep dish Pizza , Beef Roll and a Chicago hotdog! Plus Rich gave us other great food options/restaurants to visit! The Art Museum wasn’t on the tour but Rich guided us to the museum. A must seeing for Art Lovers. Amazing trip, would highly recommend.
Interesting, informative and very tasty!
JH7142,
Oct 26, 2025
- Review from Tripadvisor
5.00Rich was very familiar and well informed of all that is “Chicago”. We enjoyed all of our stops and learning about the history as well as tasting the wonderful foods.
An Outstanding Experience with Chicago Dave!
165ritaj,
Oct 26, 2025
- Review from Tripadvisor
5.00What a great, cumulative tour of Chicago! We had the good fortune to have Chicago Dave as our guide through the city. He really knows his stuff and is VERY passionate about his hometown and its history. I wish I had a transcript of everything he told us because it was sooo much, but extremely interesting. That's the thing about Chicago Dave. He piqued your interest and made you want more. My only regret is that we did this tour on our last day in Chicago rather than our first due to weather. I wish the weather had been cooperative and we'd been able to do it earlier in our trip so that we had time to digest all the information and revisit some of the locations. There are only 3 food stops, but they are delicious and offer very generous servings. You won't be hungry at the end. Plus you'll know so much more about the history of Chicago and its amazing architecture. I will do this tour again on my next visit to Chicago. Thank you, Chicago Dave! You're the Best!
Amazing 😍😍😍
mohamedkD2761BK,
Oct 22, 2025
- Review from Tripadvisor
5.00Rich is an amazing tour guide , he showed us all chicago with the famous food . We had so much fun . You need to book this tour with Rich
Great Chicago tour
maureen m,
Oct 21, 2025
- Review from Viator
5.00It’s a great tour, really felt that I learned something , while having a great time. Rich was one of the most knowledgeable guides I’ve ever had on a tour. He made me want to come back.
Highly recommend this tour for a great overall view of Chicago
KimbaWP,
Oct 20, 2025
- Review from Tripadvisor
5.00This tour was a great 1/2-day experience of Chicago - it covered the main sights and food. Our tour guide Rich was excellent - he told us what to expect, knew lots of history, was interesting, and took care of our needs. He also was great about recommending nearby restaurants and shows.
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Operated by Intrepid Urban Adventures - USA