8 Best Walking Tours in Chicago (from a Local)

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If you’re looking for the best walking tours in Chicago, this local girl has you covered!

Chicago is a beautiful city with so much to see and do. From historic architecture to world-famous museums, we’re here to help you create a memorable itinerary. And what better way to take it all in than by exploring on foot?

Read on for our top picks for the best walking tours in Chicago.

Why Take Walking Tours in Chicago

Walking tours are the perfect way to slow down and experience a city.

You’ll learn so much about Chicago that you never would have known otherwise, and you’ll get to see some of the Windy City’s most iconic landmarks up close and personal. 

Best of all, walking tours are relatively inexpensive—much cheaper than taking a bus or driving around on your own.  

The Best Walking Tours in Chicago

Are you ready to explore the vibrant city of Chicago on foot? Look no further than the best walking tours in the Windy City. With its iconic skyline, rich history, and diverse neighborhoods.

There are several great walking tours to choose from in Chicago. Below are just a few of my favorites.

The Chicago Architecture Tour

This tour covers some of Chicago’s most famous buildings while sampling the best foods in the city.

You’ll learn all about the city’s rich architectural history while getting some great views along the way. If you want to explore more options to see the architecture of Chicago, check out this article on the best Chicago architecture tours.

woman standing next to mural

The Gangster Tour

Chicago has a long history of organized crime, and this tour covers some of the most famous gangsters who called the city home, including Al Capone, Bugs Moran, and Hymie Weiss.

You’ll hear all about their crimes (and even visit some of the sites where they occurred), as well as how they impacted Chicago’s development over the years.

Chicago Favorites Ultimate Food & Walking Tour

This tour takes you to some of Chicago’s best stops for legendary eats. You’ll get a taste of classic Chicago dishes like pizza, Italian beef sandwiches, and more.

Make sure you arrive hungry because Chicago is a foodie town and serves some of the best bites in the US!

Underground Donut Tour

This has to be the sweetest of all walking tours in Chicago. Nothing can satisfy it like a donut. This tour will take you into the temples of tasty confectionaries. There are some terrific places in Chicago for a donut and they offer vegan, gluten-free, and nut-free varieties.

Chinatown Food and Walking Tour

If you are short on time and want to visit one of Chicago’s neighborhoods, this tour is for you. Alternatively, you can take your time and visit Chinatown for several family-friendly activities.

On this tour, you’ll feast on foods like dumplings and duck. The area has many shops that you can visit for souvenirs too.

Chicago Architecture Tour of the Underground Pedway

Chicago may be one of the few cities in American with underground streets. They were built in response to the city’s harsh weather. Believe me, winters in Chicago can be brutal with the lake effect! It’s now a hub for retail shops, restaurants, and services and you’ll explore the pedway that connects various buildings and spaces in downtown Chicago.

Downtown Pizza Tour

If you are a fan of pizza, then you are really in for a treat. Chicago loves deep dish, but we’ll eat thin crust too. With names like Giordano’s, Lou Malnati’s, Pizano’s, your taste buds will be in pizza heaven on this tour. It’s a good thing you will be walking, because the city is not shy when it comes to serving up delicious slices.

👣Book the Downtown Pizza Tour

Architecture Walking Tour: Dazzling Interiors™ of the Loop


If you love architecture, gilded trimmings and fancy chandeliers, this is the tour for you. Chicago has incredibly beautiful facades and interiors there were built after the Great Fire. You’ll be amazed at the beauty that still looks stunning after so many years.

Final Thoughts on the Best Walking Tours in Chicago

Whether you’re a resident of Chicago or just visiting for a short time, taking a walking tour is a great way to see the city in a whole new light.

So put on your comfortable shoes, grab a map (or better yet, book a tour!), and enjoy exploring everything that Windy City has to offer! And if you’re not up for the walking, there’s always the Chicago Big Bus Tour.


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