things to do in Chicago, IL

Follow Chicago’s movie trail with a local actor guide

Sail Lake Michigan for sweeping views of Chicago’s skyline

Sail Lake Michigan with live blues from Michael Charles and his band

See Chicago’s skyline from Lake Michigan on an evening sail

Watch Navy Pier fireworks from the water with Chicago skyline views

90-minute group sail for Navy Pier fireworks and Chicago skyline views

Discover the sweeter side of wine this Halloween

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

Self-drive pontoon on the Chicago River with Navy Pier fireworks

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

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

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

Taste four Chicago pizza styles on a guided West Loop walk

Visit four Chicago pizzerias and compare four pizza styles by bus

Cruise and swim aboard a spacious Sea Ray with room to lounge

Help open the barn with hands-on farm animal care

Discover armadillo behavior and environmental importance

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

Cruise Lake Michigan with a full kitchen, two bathrooms, and skyline views

Make your celebration hands-on with cookies and personalized party touches

Swirl frosting, add colorful toppings, and make the celebration your own

Design your own mini cake, then take it home or dig in

Take home six cupcakes decorated by you

Island tunes, skyline views, and a full bar on the Chicago River