What would you do for a shot at $4,000? Crash a volleyball game at Oak Street Beach? Convince a stranger to let you tour their apartment? Would you even get a Chicago flag tattoo? Now’s your chance to prove your mettle.
On October 4, Boppn, a social event brand specializing in immersive scavenger hunts, is bringing their whimsical flagship competition to Chicago after successful runs in New York City and San Francisco, California. Over the course of five hours, each team will choose their own adventure by picking from hundreds of Chicago-specific tasks on the Boppn app, with destinations ranging from iconic landmarks to underground gems. Each completed task—assigned a point value—is submitted via the app with a picture or video and reviewed in real time. The team that’s tallied the most points by the five-hour mark is crowned the winner.
While the overall intent of Boppn’s events is to foster connection and community, there’s a particularly strong incentive for participants: a $4,000 grand prize. Along with the abundant bounty, participants will compete for prizes from Alice & Wonder, Third Coast Hospitality, Lettuce Entertain You, Four Corners Hospitality, FleetFeet Chicago and more favorite local spots. All participants are welcome to celebrate their gamesmanship during a private afterparty at Joe’s on Weed St.

Inspired by the scavenger hunts of his ‘90s childhood, Boppn CEO and cofounder Jerry Goosenberg wants to recreate those unforgettable stories for the world at large. “This generation is way more adventurous than people give it credit for,” Goosenberg says. “The rise of the in-person, sometimes unconventional, events proves it. Our scavenger hunts are designed to bring together friends—and friends of friends of friends—while getting the opportunity to show off and uplift iconic local spots.”
Tickets are limited and cost $33–$40. Boppn will allow teams of fewer than six people to sign up until Wednesday, September 24, and full teams of six to eight people can sign up until capacity (1,200 people) is reached—which is expected. Buy tickets and learn more here.