About Chicago Captain

Chicago Captain connects customers with USCG-licensed captains for boat charters on Lake Michigan and the Chicago River. We offer scenic cruises, dive charters, corporate events, fishing trips, sailing instruction, fireworks cruises, and Playpen social cruises.

Our Mission

We are a social enterprise. Revenue from every charter funds Sail Shop Chicago NFP, a 501(c)(3) nonprofit providing maritime scholarships and community sailing programs to underserved youth in the Chicago area.

Why Chicago Captain?

• Every captain is USCG-licensed and independently vetted
• AI-powered matching finds the right captain for your trip
• Your booking directly funds maritime education scholarships
• Seven charter types covering everything from corporate events to deep-water diving