Best 122 things to do in Chicago, IL

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

Walk Pilsen for tacos, cocktails, and mural-filled streets

Charter a 48 ft Sea Ray Flybridge for up to 13 guests on Lake Michigan

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

Private 37' Sea Ray Sundancer cruise for up to 13 guests

Cruise on a 46 ft Sea Ray Express with up to 13 guests

Cruise Chicago by private boat on a 50 ft Sea Ray Sundancer, up to 13 guests

Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

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

Sail Lake Michigan for Navy Pier fireworks views on a private charter

Cruise about two miles offshore for wide-open Chicago sunset views

Speed across Lake Michigan with your own music and skyline views

Cruise offshore from Navy Pier for fireworks and skyline views

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

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

Charter a private 38' yacht on Lake Michigan for up to 13 guests

Eat a donut, then head up to the Willis Tower Skydeck

Walk the Chicago Loop to see hidden interiors and Millennium Park

Cruise the Chicago River on a private boat with local architecture stories

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft

Fly over Chicago landmarks with a private helicopter for up to 3

Take the controls in a 30-minute helicopter intro flight

Walk through Boston for donut tastings and local history

Taste your way through downtown Boston on a private donut walk