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

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

Overview

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

City: Chicago

Wed 05 Nov

Other dates

You can choose the date already on the booking website

Starting at $90.85

Make a reservation

Wed 05 Nov

Starting at $90.85

Make a reservation

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What's Included

Learn about Chicago’s rich history from a local expert guide

Taste iconic Chicago foods: hot dogs, deep-dish pizza, and Italian beef.

Walk through the historic Chicago Theater, a city icon

See the famous Cloud Gate sculpture in Millennium Park

Use local transportation to travel between the two halves

Enjoy some classic Chicago-style popcorn

Get tips on more sights, activities, and dining during your stay.

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.

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.

City of Chicago - City Hall

We’ll pass the City Hall-County Building, home to the City of Chicago and Cook County governments.

Chicago River

Feel like a local as you walk past iconic buildings, enjoy stunning skyline views, and share in the daily commute along Chicago’s main artery.

Wrigley Building

Next, we’ll pass the Wrigley Building on the Magnificent Mile, built between 1920 and 1924 to house the Wrigley Company's headquarters.

Tribune Tower

Then, we’ll pass the Tribune Tower, a 463-foot, 36-story neo-Gothic skyscraper at 435 North Michigan Avenue.

Millennium Park

Next, we’ll visit picturesque Millennium Park, home to the iconic Bean sculpture. Your guide will then offer recommendations for more sights, lunch spots, or drinks.

Cloud Gate

We'll pass the Cloud Gate sculpture, also known as 'The Bean,' the centerpiece of Millennium Park.

River North

On the food part of the tour, we’ll start with the iconic Chicago-style hot dog, followed by the world-famous deep-dish pizza. After indulging, we’ll taste one more local favorite before wrapping up with a classic Italian beef sandwich at a true Chicago institution.

Historic Water Tower

After, we’ll pass the beautiful Water Tower, built in 1869 to house a water pump drawing from Lake Michigan. It’s the second-oldest water tower in the U.S.

The Loop

At the end, stroll through the main streets near the Loop, where museums, restaurants, bars, historic landmarks, and modern architecture blend together.

Show 8 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (945)

mariasarandeva

Mar 2025

Great tour of Chicago by Kevin! I only had a couple of hours in the city and the tour provided a nice mixture of architecture, history and food - more than I could hope for in the time I had in Chicago. Thanks a lot, would highly recommend!

Isabelle_R

Mar 2025

Great half day activity! Our guide, Kevin Meskan, was enthusiastic, knowledgeable, interesting, and set a dood pace. Awesome food stops!

lesliepZ5396VA

Mar 2025

Kevin did an outstanding job! Very knowledgeable, kind and eager to answer questions! This tour gave us a great overview of Chicago. Food was terrific and found the history behind each dish very interesting!