Top Chicago Walking & Biking Tours

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right...
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Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle...
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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...
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We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't...
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Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 45% off compared to buying individual attraction tickets. This multi-attraction pass, valid...
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There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3-hour guided walking and food tour through the Chicago Loop,...
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The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour...
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Join this 3-hour tour of Chicago's food scene, and see what sets this friendly mid-western metropolis apart. On this 12 person maximum walking tour of...
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Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, America’s longest running city bicycle tour...
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Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown...
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The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour...
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This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold...
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Taste all of Chicago’s classic eats on this 4-hr guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike...
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Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle...
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Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of...
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On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor...
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There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This...
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Book Directly With Windy City Ghosts and save $5/person.Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy...
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Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic...
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Wind & Souls uses the ghosts of Chicago’s past to recreate a city that was and is no longer. Theater fires and the Alley of...
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This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to...
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