Lake Michigan,
with a captain you trust.
Every captain USCG-verified. Every charter funds youth sailing in Chicago.
Featured boats this week
Charter aboard a hand-vetted Chicago boat. A USCG-licensed captain comes with every booking.
Book a charter. Strengthen Chicago's boating community.
Chicago Captain isn't a marketplace built somewhere else and pointed at us. It's built here, by Chicago captains, for the people who love this lake.
Captains we've verified ourselves
Every captain holds a current USCG Merchant Mariner Credential — and we've checked it. No anonymous listings. No mystery captains. You know who's at the helm before you book.
Your charter funds youth sailing
Bookings on Chicago Captain support Sail Shop Chicago, a 501(c)(3) introducing kids who'd otherwise never set foot on a boat to sailing, safety, and maritime careers. You're not just renting a boat — you're contributing.
Built by Chicago captains
We're USCG captains who run charters on this lake every week. The platform is built around how Chicago boating actually works — short season, real harbors, real weather — not a generic global template.
How Chicago Captain Works
Tell us about your trip. We match you with the right captain and boat, confirm availability, and connect you directly.
Find a captain or boat
Browse our directory of verified captains and boats — filter by harbor, trip type, and passenger count to find your fit.
Check availability
Real-time captain calendars show what's open for your date — no back-and-forth.
Connect directly
Talk to your captain before you go. They'll confirm details, share what to bring, and make sure your day on the water is the one you wanted.
Ready to charter a Chicago boat?
Whether it's a sunset cruise, a fishing run, or a Mackinac trip — you'll go with a captain you trust, on a boat we know, supporting a community we love.