Chicago in a Day: Food, History & Architecture Walking Tour

Overview

Available languages

English

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 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.

10 minutes • Admission Not Applicable

Chicago Pedway

Weather permitting, we'll explore the Chicago Pedway, a network of underground tunnels used daily by locals and commuters, especially in winter.

20 minutes • Admission Not Applicable

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

Small Group Chicago in a Day

Private Chicago in Day

Reviews

4.92

1,152 reviews

Total reviews and rating from Viator & Tripadvisor

1091

A Taste of Chicago History, Architecture, and Food
B9145EVbarbaraw,,Jan 13, 2026
- Review from Tripadvisor
5.00
We 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
5.00
We 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
5.00
Informative; 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
5.00
Our 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
4.00
Dave 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
5.00
A 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
5.00
I 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
5.00
Highly 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
5.00
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.
Highly recommend
joycesA2212HD,,Dec 8, 2025
- Review from Tripadvisor
5.00
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!