Charter a Chicago boat

A USCG-licensed captain comes with every booking. Every charter contributes to Sail Shop Chicago, our 501(c)(3) youth-sailing nonprofit.

Captains USCG-verified by usCaptain included on every charter

Charters are done for the 2026 season

You can send a request for a trip next season, and we'll be in touch. Questions? Call (773) 910-2088 or email info@chicagocaptain.org.

Just for Fun

Just for Fun

Diversey40′Up to 11
$325/hourView →
PEONY
Captain included

PEONY

Burnham Harbor33′Up to 6
$162.5/hourView →
SeaQuest II

SeaQuest II

Hammond Marina, IN47′Up to 22
Contact for pricingView →
Vera

Vera

Belmont Harbor37′Up to 12
Contact for pricingView →
Vista

Vista

Belmont Harbor37′Up to 12
Contact for pricingView →