| 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 | | | | | | |
| Paint Nite | | Painting Event at Local Bar | | Painting parties are held at local bars and restaurants, where attendees enjoy cocktails, socialize, and paint | | | | | | |
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| Studio Movie Grill | | Ticket to Newest Movies | | A wide selection of new releases and cult classics is projected on towering screens as viewers watch from leather recliners and tables | | | | | | |
| 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 | | | | | | |
| Captain Hook's Charter Fishing | | Perch-Fishing Trip | | Perch jerkers join a 60-foot lake michigan boats to catch perch averaging 6–10 inches; makes a great Christmas or birthday gift for fishers | | | | | | |
| Go City Card | | Chicago Explorer Pass | | Card grants free admission to 3 or 5 Chicago museums, tours, and attractions, chosen from over 20 options | | | | | | |
| Kingston Mines | | Blues Concert for Two | | Legendary blues club stages performances by equally legendary blues musicians seven nights a week | | | | | | |
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| 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 | | | | | | |
| Seadog Cruises | | Boat Tour or Thrill Ride | | Speedboats zip past famed Chicago landmarks along the lakefront and river; informative narration on city’s history and architecture | | | | | | |
| The Comedy Bar | | Standup: The Comedy Bar | | National headliners and up-and-coming comedians take the stage at legendary club’s space inside Gino’s East River North | | | | | | |
| The Logan Theatre | | Movie Outing for Two | | Historic theater features current releases and classic films | | | | | | |
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