things to do in Chicago, IL

Paddle Chicago's lakefront with skyline views and basic instruction

Watch Chicago fireworks on a 90-minute tiki bar cruise

Paddle Chicago River routes in a single or double kayak

Watch Navy Pier fireworks from a private yacht

Explore the history, neighborhood culture, and presidential ties of Chicago's South Side

Taste Lincoln Square’s European roots and Silk Road flavors on foot

See Chicago from the water aboard a former Navy tactical boat

Paddle Lake Michigan from Ohio Street Beach for two hours

Paddle Lake Michigan for Chicago skyline views

Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises

Live Electric Brew jams aboard a historic Chicago fireboat

Private Lake Michigan fishing with an expert crew

Paddle Goose Island and downtown as Chicago lights reflect on the river

Bring your group aboard for a captain-led Chicago outing

Live stand-up, touring comedians, and skyline views aboard a historic fireboat

See holiday lights, market traditions, and Chicago's tree on a downtown stroll

Enjoy a Chicago charter with a USCG-licensed captain and 15+ years of experience

Taste Chicago's holiday flavors and festive sights on foot

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

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

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks

Cruise Chicago’s waterfront with a certified EMT captain

Captain for hire on Lake Michigan, with payment options and holiday rates

Cruise Chicago with a flexible captain for your 3–4 hour charter