things to do in Bolingbrook, IL

Take the controls in a 30-minute helicopter intro flight

Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river

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

Private skyline cruise with a local perspective

Taste Dublin’s doughnuts while uncovering city stories on foot

Create a one-of-a-kind poured-paint figurine

Cruise a 47-foot Carver with space to relax, dine, and play your music

Speed across Lake Michigan with your own music and skyline views

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

Explore historic prison spaces at your own pace

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Taste Chicago classics and discover the stories behind the city’s signature dishes

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

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

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

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

Walk Edinburgh’s Old Town and sample doughnuts and pastries in 2 hours

Paint a doormat that matches your style

Make your Chicago celebration a private day or night on the water

Mark a romantic occasion with a private flight above the landscape