Chicago in a Day: Explore Food, History, and Iconic Architecture
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
Private Chicago in Day
Small Group Chicago in a Day
Reviews
1,073 reviews
Total reviews and rating from Viator & Tripadvisor
Dave was an incredible...
grieger2003,
Sep 2, 2025
- Viator
5.00Dave was an incredible tour guide- one of the best i have ever had! Not only was he knowledgeable about all the spots we visited, he was so thoughtful and caring about the people on the tour. He didn’t race from one spot to another- he walked backwards as he talked to us to ensure we were all together and we were safe. One of my friends was extremely reticent about a 4 hour walk due to a bad knee, and Dave often checked with her to make sure she was feeling ok! She loved Dave and his tour! I wish all tour guides were as knowledgeable and concerned about the needs of the people on their tours!
David was an awesome...
Abbigail W,
Aug 31, 2025
- Viator
5.00David was an awesome guide of the city. Chicago is an amazing town and we learned so much. The food and architecture is top-notch. We had a great time and our group was fun!
Dave was a fun and...
Shannon S,
Aug 24, 2025
- Viator
5.00Dave was a fun and enthusiastic guide. He added lots of personal details from his experience in Chicago. He planned ahead for stops to sit, use the restroom and find shade.
This was a great tour led...
Eugene K,
Aug 18, 2025
- Viator
5.00This was a great tour led by a Chicago Dave. His knowledge of Chicago’s architecture and history are top notch. The tour was very enjoyable and each city around the globe needs a tour like this.
Great Tour
Tammy G,
Aug 16, 2025
- Viator
5.00– Our tour guide was amazing. He had a thorough understanding of the city. Answered questions. Gave recommendations. Great enthusiasm and attitude.
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Operated by Intrepid Urban Adventures - USA