Interactive Walking Tours of Chicago from Stray Boots (50% Off). Four Options Available.

89% of 151 customers

from $12
Value Discount You Save
$24 50% $12
Limited time remaining!
Over 370 bought
Limited quantity available

In a Nutshell

Clues, trivia, and riddles lead explorers through vibrant neighborhoods via the Stray Boots iPhone or Android app

The Fine Print

Expires 360 days after purchase. Limit 1 per person, may buy 4 additional as gifts. Limit 1 per visit. Valid only for option purchased. Online registration required. iPhone or Android phone required for scavenger hunt clues, trivia, and riddles. Rain or shine. Must use promotional value in 1 visit. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Giving this as a gift? Send it instantly with one of our festive e-cards, or print a handy gift envelope and card.

Early adventurers braved unknown lands armed with little more than all-terrain horses, a coal-burning GPS system, and plasma TVs useful only to barter for lukewarm porridge. Revel in the convenience of more advanced exploring with this Groupon.

Choose from Four Options

  • $12 for two tickets to the zone of your choice (a $24 value)
  • $24 for four tickets to the zone of your choice (a $48 value)
  • $40 for two tickets to all regular zones (an $80 value)
  • $80 for four tickets to all regular zones (a $160 value)

Purchasers choose from the Magnificent Mile, The Loop, Navy Pier, or Lincoln Park zones, or they can explore all four.

Stray Boots

Stray Boots is an interactive tour that sets friends and family members loose on an exhilarating, knowledge-fueled undertaking guided by clues, trivia, and riddles. They operate in cities across the country, dividing them into special themed tours that contain the historical sites, local areas of interest, or eccentric child mayors unique to each city. During the explorations, clues point the way to cultural hot spots, which Stray Boots communicates via their official mobile app. At least one player on the team will need an iPhone or Android phone to receive clues, and none of the self-guided tours require previous knowledge of the city. Adventurers play at their own pace—most tours take two to three hours to finish—which allows them to spend more time learning about the city and photographing vibrant fire hydrants for aquacentric scrapbooks.


89% of 151 customers

  • “The tour was awesome, engaging and fun!”

  • “EXCELLENT adventure!! A real eye opener into a city that I lived in all my life!”

  • “Wonderful and so much fun. A great way to see the sights, learn the history and do it at your own pace.”

For those looking to get out of the house with the ladies
After-work activities, from bites and brews to bowling and bottle service
Choose your deal:
Two tickets to any game zone
$24 list price - 50% off - Save $12
Over 250 bought
Four tickets to any game zone
$48 list price - 50% off - Save $24
Over 70 bought
Two tickets to all regular game zones
$80 list price - 50% off - Save $40
Over 30 bought
Four tickets to all regular game zones
$160 list price - 50% off - Save $80
5 bought