| Water-Park Outing | Turtle Splash Water Park | $20 $10 | | | | Boat Rental | Vantage Boat Share | River North Marina on the Riverwalk | $200 $99 | | | |
| Sunset Segway Tour | Bike and Roll Chicago | Millennium Park | $75 $39 | | | | Jet Ski Rental | Windy City Watersports | Uptown | $85 $39 | | | |
| Mini Golf and Beers | Highland Park Golf Learning Center | $38 $19.99 | | | | Fireworks and Sunset Cruises | Chicago Cruise Events | DuSable Harbor - Anita Dee II Yacht | $31 $12 | | | |
| Adventure Package with Ziplining | Aerial Adventures Lake Geneva | Lake Geneva | $100 $49 | | | | Minor-League Baseball Game & Cap | Kane County Cougars | Fifth Third Bank Ballpark | $26.50 $9 | | | |
| 5K Obstacle Race | Rugged Maniac 5K | CPX Sports | $100 $40 | | | | Chicago Explorer Pass | Go City Card | $40.50 | | | |
| Round of Golf and Beers | Highland Park Country Club | Sunset Terrace | $93 $39 | | | | Perch-Fishing Trip | Captain Hook's Charter Fishing | | | | |
| Horseback Riding | Sarah's Stables, INC | Little Palestine | $40 $23 | | | | 5K to Benefit HAE Research | HAE in Motion 5K | Danada Forest Preserve | $25 $14 | | | |
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