| Tall Ship Red Witch | | Fireworks Sail on Tall Ship | | Passengers relax on Chicago’s only wooden tall ship while viewing fireworks; Readers’ Choice award winner | | | | | | |
| Skybox on Sheffield | | Cubs Rooftop Experience | | Enjoy iconic Wrigleyville experience from a three-tiered rooftop with food, beer, and wine | | | | | | |
| SeaBreeze Charter LLC | | Sailing Charters | | American Sailing Association–certified captain entertains passengers during two-hour charters on Lake Michigan; BYOB and food | | | | | | |
| Chicago Cruise Events | | Fireworks and Sunset Cruises | | Enjoy cocktails from a cash bar as you cruise on Lake Michigan and watch fireworks light up the Chicago skyline | | | | | | |
| Go Bananas | | Indoor Amusement Center | | Bumper cars, a bounce castle, a mini roller coaster, and abundant arcade games enthrall youngsters | | | | | | |
| Chicago Beer Experience | | Beer-Tasting and Bar Tour | | Each neighborhood walking tour visits locally owned, off-the-beaten-path establishments like microbreweries, bars, and beer and wine stores | | | | | | |
| 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 | | | | | | |
| Enchanted Castle | | Enchanted Castle | | Guests enjoy an afternoon of fun with attractions such as bumper cars, go karts, and laser tag, plus tokens for the game room | | | | | | |
| Aerial Adventures Lake Geneva | | Adventure Package with Ziplining | | Adventurers fly on 3 zip lines, climb ropes into the treetops, and play a soccer-type game on a field with teams and a ball | | | | | | |
| Vantage Boat Share | | Boat Rental | | Passengers cruise the Chicago River on a luxury pontoon or electric boat | | | | | | |
| Dells Army Duck Tour | | Amphibious Tour | | Amphibious, WWII-era vehicles take groups on one-hour trips through the natural landscapes and waterways of the Wisconsin Dells | | | | | | |
| Fox Valley Park District | | Water Park | | Publicly maintained waterpark with attractions such as a zero-depth leisure pool, water slides, kid-play areas and sand volleyball courts | | | | | | |
| 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 | | | | | | |
| Raging Waves Waterpark | | Raging Waves Waterpark | | Full-day visit to park with rides, slides, and children’s play area | | | | | | |
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