things to do in Oak Park, IL

Cruise Chicago’s river in a vintage 1950s Milo Craft

Take the controls in a 30-minute helicopter intro flight

Bike Miami Beach and sample local food with a guide

Explore historic prison spaces at your own pace

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

Ride Chicago’s 1920s–30s gangster trail with actor guides

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

Paddle the Chicago River after dark with city lights and stories from your guide

See Chicago's northwest suburbs and the Fox River from the air

Explore Chicago through social adventures with fellow solo travelers

Explore Old Joliet Prison after dark at your own pace

Hire a US Coast Guard licensed captain for your Chicago boat day

Tour and tasting for two with a tasting room reservation and wine

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

Paint a doormat that matches your style

Private 40' Sea Ray yacht rental in Chicago for up to 13

Start first, save more, and skip room waits

Eat your way through Chicago’s Chinatown with 5 seated tastings