Now at Navy Pier Marina—Chicago's ONLY 49-Passenger Sailing Catamaran!

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:
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• 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

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

INQUIRE FOR 2026

BERNARD
Private Charters for Groups of 6 or Less

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Type of Sail	Guest Count	Mon-Thur	Fri-Sun
Private Charter	Up to 6 Guests	$444	$498

YOUR SAILING ADVENTURE BEGINS HERE!

​​Come Sailing is Chicago’s home for authentic sailing adventures. From social public cruises on our stable catamaran, CITY CAT, to intimate private voyages on the classic sailboat BERNARD, we offer a personalized alternative to the large-scale commercial tours. Join us at our new home in Navy Pier Marina to experience the skyline as it was meant to be seen—from the deck of a sailboat. Take a break, Come Sailing, and let the lake breeze gently whisk away the stress of everyday life.