| Tall Ship Windy | | 75-Minute Sailing Tour | | A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan for about 75 minutes | | | | | | |
| WickedBall | | Bubble Soccer | | Players don giant inflatable balls while ramming into other players and bouncing off the ground during bubble-soccer games | | | | | | |
| Players Sport & Social Group | | Chicago Field Day and Beers | | Inaugural event puts a beer-soaked spin on tug-o-war, scavenger hunts, and new games such as the Battle Ball Gauntlet | | | | | | |
| Vantage Boat Share | | Boat Rental | | Passengers cruise the Chicago River on a luxury pontoon or electric boat | | | | | | |
| City Segway Tours (Chicago) | | City Segway Tours | | Take a guided Segway tour past Chicago landmarks including Soldier Field and the Field Museum, and enjoy views of Navy Pier and the skyline | | | | | | |
| Hang Gliding Chicago-Milwaukee | | Tandem Hang Gliding | | Give the gift of flight as students learn basic hang glider controls, safety, and take their first flight strapped to a seasoned instructor | | | | | | |
| Sluggers World Class Sports Bar | | 15 Batting Cage Tokens | | Sports bar’s upstairs game room includes batting cages where guests can practice their swings and crush fastballs | | | | | | |
| Absolutely Chicago Segway Tours | | Absolutely Chicago Segway Tours | | Ride up to some of Chicago’s most iconic landmarks during Museum Campus, Gangster history tours, and fireworks displays | | | | | | |
| Best Tours | | Cupcake Tour of Chicago | | Tours make six stops along Michigan Avenue, visiting a century-old shop, one with 50 varieties of cupcake, and another with gelato | | | | | | |
| Sidewalk Food Tours of Chicago | | Walking Food Tours | | Enjoy a roving lunch of five different tastings while learning about the history and culture of either River North or Wicker Park | | | | | | |
| Wrigley View Rooftop | | All-Inclusive Cubs Game | | While enjoying all-inclusive refreshments, peer over Wrigley Field’s left-field wall and watch the Cubs take on MLB rivals | | | | | | |
| PAWS Chicago | | PAWS Chicago 5K Run or Walk | | PAWS Chicago's annual run or pet-friendly walk supports saving homeless cats and dogs; participants get an event bottle | | | | | | |
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| Bigfoot zipline | | Bigfoot Zipline Tours | | Soar from tower to tower on seven different ziplines while reaching heights of up to 100 feet at this Wisconsin Dells destination | | | | | | |
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