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
Is this tour child-friendly? Yes! This tour is suitable for families. Children under 4 years old can join free of charge. A reduced child price applies for children aged 4 to 11.
Will food options or portion sizes very? Food offerings and portion sizes may vary depending on the season and the stops visited on the day of the tour. However, the total amount of food included is always designed to equal a full meal.
Is this tour suitable for all ages and fitness levels? Yes! This tour is suitable for guests of all ages and fitness levels. Please note that it includes approximately 4.8 to 6.4 km (3-4 miles) of walking. at a relaxed pace with regular stops.
Can dietary requirements be accommodated? Vegetarian options are available. Unfortunately, we are unable to accommodate other food allergies or dietary preferences. Please let us know in advance if you require a vegetarian option so we can plan accordingly.
What happens if the weather isn’t great? Experiences run rain, shine, or snow, so please dress appropriately for the weather on the day of your tour.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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.
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
Options
Private Chicago in Day
Small Group Chicago in a Day
Reviews
1,153 reviews
Total reviews and rating from Viator & Tripadvisor
Saw and tasted Chicago
Getaway11810074528,,Feb 7, 2026
- Review from Tripadvisor
5.00Loved the tour. The guide, Rich, was great. Learned a lot about Chicago architecture and history. And were introduced to many of the great food spots that Chicago is known for. There are many ways to see the architecture of the city but with a walking tour you can also experience the inside of the buildings too. They were amazing!
A Taste of Chicago History, Architecture, and Food
B9145EVbarbaraw,,Jan 13, 2026
- Review from Tripadvisor
5.00We could not have asked for a better experience or tour guide to learn about Chicago’s history, buildings, and iconic food. Rich was very knowledgeable and made the tour extremely fun and interesting with his stories, anecdotes, and great food choices. We highly recommend this tour for an in depth and immersive view of Chicago in 4 1/2 hours!
Fun introduction to the heart of Chicago
P3121UDsusanb,,Jan 9, 2026
- Review from Tripadvisor
5.00We thoroughly enjoyed our tour with Dash. He was very congenial and a fount of knowledge about all things Chicago …past, present and future. We loved that he took us inside so many of the historic buildings to see the opulent interiors. Along the way we sampled the original Chicago brownie, the Chicago hot dog, the Italian Beef Sandwich and stuffed pizza. We strolled along the Riverwalk and even took a ride on the city’s iconic EL. It was a fun and interesting introduction to the heart of Chicago!
Informative; our guide...
Kerrie S,,Jan 8, 2026
- Review from Viator
5.00Informative; our guide Dave was passionate and knowledgeable. It was great to try Chicago’s iconic foods too!
Amazing first visit to Chicago!
Safari14531711311,,Jan 5, 2026
- Review from Tripadvisor
5.00Our first time seeing Chicago. Rich was our guide and he did an awesome job of showing us all the best things about Chicago! We saw beautiful buildings, we learned about Chicago history and we ate delicious food! We have been on tours in other places and this was by far my favorite!
Good experience and would recommend.
Michael T,,Jan 4, 2026
- Review from Viator
4.00Dave was extremely knowledgeable about Chicago. He gave excellent histories about various places and foods. I appreciated his candor and enthusiasm. The places he took us for food were solid and enjoyable. His ability to help us appreciate our surroundings was a pleasure. At times, his stories were sometimes complicated and difficult to follow - alas that is history sometimes. I think shortening the tour by 30-45 minutes would have made it better.
Great Chicago Introduction
michaelbJ7305XJ,,Dec 30, 2025
- Review from Tripadvisor
5.00A fantastic tour of Chicago history, architecture, and food. Out guide, Dash, was knowledgeable and entertaining as he pointed out some hidden gems throughout the city.
A Wonderful Introduction to Chicago
50margueritec,,Dec 27, 2025
- Review from Tripadvisor
5.00I booked this walking tour for my family for the first day of a week-long vacation in Chicago. Our young adult daughters enjoyed the tour, led by Dash, as much as my husband and I did. We saw much of the downtown, stopping in beautiful buildings and a couple restaurants for tasty local dishes. A surprise highlight was taking the train around the Loop. Highly recommend Dash—so informative and entertaining—and this tour!
Highly recommended! I was...
Minjeong S,,Dec 16, 2025
- Review from Viator
5.00Highly recommended! I was able to experience Chicago’s architecture and food culture overall. Rich was very friendly and provided lots of interesting information.
Happy I Went On This Tour
Matt G,,Dec 13, 2025
- Review from Viator
5.00Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.
From US$100.95
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Operated by Intrepid Urban Adventures - USA