Best 316 things to do in Deerfield, IL

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

Cruise Chicago’s lakefront for skyline and Navy Pier views

Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours

Choose your paddlecraft for a self-guided outing on the water

Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

Learn paddleboard skills for calm-water adventures

Sail Chicago's lakefront from Museum Row to Navy Pier at sunset

Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

Sail Chicago’s lakefront on a private charter with time to swim and relax

Sail Lake Michigan with Chicago skyline views

Sail Lake Michigan at sunset for Chicago skyline views from the water

Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan

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

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

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

Speed across Lake Michigan with your own music and skyline views

Cruise the Chicago River for skyline views and Riverwalk sights

Sail Lake Michigan on a private day charter with skyline views

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

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

Discover Lincoln Park’s nature and history with a local guide

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Paddle past the Wild Mile and Chicago's skyline in a single or double kayak

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