Come Sailing, Inc. - Chicago's Premier Private Sailing Charter

Introducing CITY CAT!
The Newest Member of the Come Sailing Family!

Step aboard the newest and most unique addition to the Chicago Lakefront. CITY CAT isn't just a new boat; it's a completely new way to experience the Windy City. As the only true sailing charter catamaran in Chicago, and the only sailing vessel in the city with a 49-passenger capacity, CITY CAT fills the perfect gap between small 12-passenger charters and massive tour boats.

Whether you are hosting a corporate outing, a milestone celebration, or a high-end wedding event, CITY CAT offers an intimate, upscale sailing experience with the scale and amenities of a much larger boat.

The CITY CAT Experience:

Unmatched Stability: Experience the "flat sailing" advantage. Unlike traditional sailboats that lean, CITY CAT's twin-hull design remains level and stable, providing the most comfortable and confident ride on Lake Michigan for all your guests.
The Best Seats in the City: For those seeking a thrill--or the ultimate spot to lounge--our forward bow trampolines allow you to relax just feet above the waves as the rush beneath you.
All-Weather Comfort: With plenty of covered seating areas, your event is protected from the midday sun or a passing lakefront shower, ensuring your guests stay comfortable no matter the weather.
Built for Entertaining: Featuring a dedicated onboard bar/buffet area, CITY CAT is purpose-built for seamless food and beverage service.

Experience the "Purr-fect" blend of performance, luxury, and Chicago pride. CITY CAT is ready to welcome your group of up to 49 for a sailing experience unlike anything else in Chicago.

CITY CAT
Chicago's Premier 49-Passenger Sailing Charter Cat

Type of Sail	Guest Count	Mon-Thur	Fri-Sun
Public Ticket	Individual	$75	$90
Private Charter	Up to 24 Guests	$1,800	$2,160
Large Private Events	25 - 49 Guests	$75/Guest	$90/Guest

* Rates are based on 2 hours of sailing on CITY CAT.

** Public ticket calendar for the 2026 season will open soon. Join our newsletter to be the first to know!

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