Explore Chicago in a Fun Way!

Take a Chicago walking tour that plays out like a game on your phone, all on your own schedule. See how it works!


For large groups (>12 people), check out our scavenger hunt events in Chicago for 
corporate team buildingschool field trips, and other large groups!

Magnificent Mile $5 Intro to Stray Boots Chicago
$5 per person

Designed to rival New York's 5th Avenue and Paris's Champs Elysees, the Mile is big on history and haute couture.

The Loop Visual Arts and Business Smarts
$12 per person

Navigate Chicago's deepest urban canyons, as you discover the city's most iconic, interesting, and influential spots.

Lincoln Park Local Grub in the Historical Hub
$12 per person

Dust off your top hat and frock coat and make your way to Lincoln Park to discover the cultural and historical center of Chicago.

The Perfect Chicago Date Romance in the City
$12 per person

Let the Windy City sweep you off your feet, as you embark on a fun, romantic adventure through the city's sexiest streets.

Navy Pier Temporarily Unavailable
$12 per person

Due to major construction, this tour will be unavailable until mid-2015. If you've recently purchased the tour, please contact us at (877) 787-2929 or support@strayboots.com for more information.

Art Institute Chicago That's Chagall, Folks! TEMPORARILY UNAVAILABLE
$12 per person

TEMPORARILY UNAVAILABLE THROUGH SUMMER Welcome to the Art Institute of Chicago, home of over one million square feet of amazing works of art from all over the world!