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Best of Chicago: Discover Art, Food, and Architecture

Best of Chicago: Discover Art, Food, and Architecture

Overview

Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city's best spots and try a local sweet treat along the way as you explore on foot.

City: Chicago

Thu 05 Jun

Other dates

You can choose the date already on the booking website

Starting at $49.96

Make a reservation

Thu 05 Jun

Starting at $49.96

Make a reservation

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What's Included

Get tips on more sights, activities, and places to eat during your stay.

Enjoy Chicago-style popcorn

Discover architectural gems like Jewelers Building and London House

Join a friendly, local English-speaking guide on a walking tour.

Stroll the Chicago Riverwalk with stunning skyline views

See the Chicago Theater, Wrigley Building, and Tribune Tower.

Conclude at Millennium Park and the iconic Bean sculpture

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 tour. Children under 6 join for free. Children ages 6-11 can join at the adult rate. Please inform us of any children in your party at the time of booking, using the special requirements box on the checkout page.
Experiences happen rain, shine, or snow. Please dress accordingly.
Suitable for all ages and fitness levels, but please note that this tour covers about 4.8 km (3 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.

What To Expect

The Chicago Theatre

We begin at the iconic Chicago Theater marquee, then explore the city.

Chicago Pedway

Weather permitting, we’ll explore the Chicago Pedway, a network of underground tunnels used by locals and commuters.

City of Chicago - City Hall

We'll pass the City Hall-County Building, home to Chicago’s government and Cook County offices.

The Picasso

Next, we’ll stop at the Chicago Picasso in Daley Plaza, a 1967 installation that transformed public art and urban planning.

Chicago River

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

Chicago Riverwalk

Weather permitting, we’ll stroll the award-winning Chicago Riverwalk, enjoying views of iconic buildings like Marina Towers, the Wrigley Building, and the Tribune Tower.

Wrigley Building

We’ll pass the iconic Wrigley Building at 400 N Michigan Ave, a historic landmark in the heart of Chicago.

Tribune Tower

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

The Magnificent Mile

Next, we’ll pass the Magnificent Mile on North Michigan Avenue, a vibrant district of shops, restaurants, and attractions, created as part of the 1909 Burnham Plan.

Chicago Cultural Center

Step inside a Chicago Landmark, the Cultural Center, where the Mayor has welcomed presidents, royalty, and dignitaries

Cloud Gate

We’ll end the tour at the Cloud Gate sculpture, also known as 'The Bean,' the centerpiece of Millennium Park.

Show 8 more stops

Cancellation Policy

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

Traveler Photos

Reviews (80)

Jenna J

Mar 2025

I had a fantastic experience on this tour and learned so much! Rich was so nice and knowledgeable. He even made suggestions for sports bars and restaurants.

David_C

Feb 2025

Provided lots interesting details throughout the walk on rainy Friday. Knew his information and communication was very clear.

andreajacobsen2

Dec 2024

It was amazing. I grew up in Rockford, IL and grew up going to Chicago a few times a year. But I never knew about its rich full history and of course its beautiful architecture. I know the boat tours are popular, but I recommend doing this one instead!! Going inside the buildings and learning about its history and viewing the ceilings and interior was amazing.