| Bike and Roll Chicago | | Sunset Segway Tour | | Easily maneuverable segway vehicles traverse the lakefront for views of the Chicago skyline, parks, and lakeside museums | | | | | | |
| Sky Zone Schererville | | Indoor Trampoline | | During one hour of open jump time, jumpers can bounce between a SkySlam basketball court, wall-to-wall trampolines, and a foam pit | | | | | | |
| Down the Line Rooftop | | Rooftop View of a Cubs Game | | All-inclusive food and drinks create a party-like atmosphere on a Wrigleyville rooftop as the Cubs take on foes inside Wrigley Field | | | | | | |
| Lakeview Baseball Club | | Rooftop View of Cubs Game | | Indulge in food and drinks while taking in a ballgame from a facility that mixes old-school charm with lush modern amenities | | | | | | |
| The Laugh Factory | | Standup Comedy | | Large lineups of top local standup talent, comedic storytelling, and themed shows | | | | | | |
| Corporate Tailgate Boat Rentals-Chicago | | Pontoon-Boat Rental | | Pontoon boats cruise leisurely up and down the Chicago River on a waterfront tour; see Navy Pier fireworks; bring your own food and drinks | | | | | | |
| Chicago Crime Tours | | Chicago Crime Tour by Bus | | Learn about more than 100 years of Chicago's crime history in a 90-minute tour of famous crime scenes and landmarks | | | | | | |
| Offshore Adventures | | BYOB Sailing Cruises | | Daytime or sunset Lake Michigan cruises delight with views of the Chicago skyline; passengers can bring their own drinks and playlists | | | | | | |
| 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 | | | | | | |
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| Go City Card | | Chicago Explorer Pass | | Card grants free admission to 3 or 5 Chicago museums, tours, and attractions, chosen from over 20 options | | | | | | |
| Best Tours (Chicago) | | Gangster Tour of Chicago | | Tour-goers take a 90-minute jaunt past iconic landmarks and mob movie filming locations while learning about Chicago’s gangster past | | | | | | |
| Skydive Midwest | | Tandem Skydive Jump | | Experienced instructors hold 30-minute training sessions before strapped-together pairs jump from planes and drift slowly back toward land | | | | | | |
| GameWorks | | GameWorks Arcade-Game Pass | | Full day of unlimited access to hundreds of interactive games with a $10 game card | | | | | | |
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