Explore Chicago in a totally new way – through six fun and fascinating interactive walking tours with your phone as your guide.

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.

Give Stray Boots as a Gift Give the gift of exploration!
$12 per person

Think that a Stray Boots tour would make a perfect gift for family or friends? We do too! Just purchase a gift certificate here. We'll send you an email with special instructions you can forward on as a gift.

Navy Pier AHOY Lotta Fun!
$12 per person

Ahoy, mate! Whether you're a swashbuckler or sailor, you'll have an amazing time navigating your way through throngs of tourists, searching for hidden treasures.

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.

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

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

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.