Take the controls in a 30-minute helicopter intro flight
Cruise Chicago’s river in a vintage 1950s Milo Craft
Ride Chicago’s 1920s–30s gangster trail with actor guides
Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings
Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river
Private skyline cruise with a local perspective
Cruise a 47-foot Carver with space to relax, dine, and play your music
Taste Dublin’s doughnuts while uncovering city stories on foot
Create a one-of-a-kind poured-paint figurine
Tour and tasting for two with a tasting room reservation and wine
Speed across Lake Michigan with your own music and skyline views
Ride a foodie bus to restaurants seen in The Bear, with tastings along the way
See Chicago's northwest suburbs and the Fox River from the air
Paddle the Chicago River after dark with city lights and stories from your guide
Private 40' Sea Ray yacht rental in Chicago for up to 13
Taste Chicago classics and discover the stories behind the city’s signature dishes
Hire a US Coast Guard licensed captain for your Chicago boat day
Start first, save more, and skip room waits
Make your Chicago celebration a private day or night on the water
Walk Edinburgh’s Old Town and sample doughnuts and pastries in 2 hours
Discover the journey from fresh grapes to wine during Chicago's harvest season
Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner
Eat your way through Chicago’s Chinatown with 5 seated tastings