Chicago Walking Tours

Experience why the "Second City" is second to none.

Our Most Popular Tours

As a large American city, Chicago is rather unique.

Known for its architecture, public art, iconic elevated transit system and 77 ethnically diverse and vibrant neighborhoods, the city is truly one of a kind.

Whether you’re interested in Loop architecture, prohibition-era speakeasys or underground passageways, our most popular tours will take you there.

Interested in a deeper dive into one of Chicago’s fascinating neighborhoods? Consider a Group or Private Tour

L Stop Tours — Let us share our amazing city with you.


See the Best of Chicago

River North: Historic Pubs

Duration: 3.5 hours Price: Adult $60

Two neighborhoods, four taverns and the perfect blend of culture, food and stories on our popular Chicago historic pub tour See available dates here.

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Underground Chicago: Pedway Tour

Duration: 2.5 hours Price: Adult $60

Experience Chicago's system of underground walkways. See available dates here.

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Loop: Home of the Modern Skyscraper

Duration: 3.5 hours Price: Adult $60

See Chicago's most historic buildings and train station. Stroll around downtown, see inside of famous buildings and ride the train around the Loop. See available dates here.

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Downtown Chicago Attractions for Instagram

What to Expect on a Tour

Smaller Groups

Tours run with a maximum of 10 participants — so you can count on personal attention. Do you have a bigger group? Check out our Groups & Private Tours page.

Ride the L

Each L Stop tour includes a short ride on the L. Transportation fees are included in the tour price.

Explore Downtown Chicago

Be an insider. Our Loop walking tours take you inside buildings and other famous sites that can't be seen by boat or bus.


From great stories and personal experiences to unique insights about the city, our local Chicago tour guides ensure a memorable experience.

Food & Beverage

Opportunities for guests to purchase refreshments are included on every tour. Check tour pages for details.

Walking & Stairs

Participants should be able to use stairs and comfortably walk during each tour experience.