things to do in Dyer, IN

Taste your way through Chicago’s West Loop with a local guide

Celebrate on the Gypsy Spirit along Chicago’s waterfront

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

Step inside Chicago Loop landmarks and trace the evolution of its skyline

Taste Chicago donuts while uncovering Fulton Market’s industrial past

Explore historic prison spaces at your own pace

Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio

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

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

Bike Miami Beach and sample local food with a guide

Hire a Polish-speaking captain for your rented Lake Michigan boat

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

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

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

Private skyline cruise with a local perspective

Taste Santa Monica’s donut culture on an outdoor walking tour

Explore Old Joliet Prison after dark at your own pace

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

Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner

Discover the journey from fresh grapes to wine during Chicago's harvest season

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

Enjoy unlimited rides and more than 50 attractions at a fall farm festival