On A Boat Sailing - Chicago, IL

Offer

Golden Sail Money-Back Guarantee

100% refund up to two weeks from departure. 50% refund up to 48 hours from departure. Full refund for weather-related cancellations. Swap dates with no fees, subject to availability.

Offer

Proposals & Engagements Cruise

This 2-hour private sailboat cruise offers a romantic sail along the Lakefront and a private experience of seeing the city from the water. It is suitable for proposals and engagement photos. Expect clear views of Chicago's iconic skyline and a waterfront experience in style and comfort. A professional photographer upgrade, custom decorating and event planning are available. Starting at $799, up to 10 guests.

Offer

Skyline Sunset Cruise

This 2.5-hour private sailing cruise offers views of the nightly summer sunset aboard Dragonfly. Enjoy the sights and sounds of Lake Michigan at sundown, including views of Chicago's historic skyline and lighting for summer photos. Bookings include unlimited snacks and soft drinks, BYOB plus beer, wine and seltzers for purchase, and complimentary ice. Starting at $949, up to 10 guests.

Offer

Chicago Lakefront Cruise

This 3-hour private sailboat cruise takes guests along Chicago's lakeshore aboard the 37' luxury sailboat Dragonfly. Expect clear views of Chicago's iconic architecture and a waterfront experience in style and comfort. Bookings include unlimited snacks and soft drinks, BYOB plus beer, wine and seltzers for purchase, and complimentary ice. Starting at $999, up to 10 guests.

Offer

Navy Pier Fireworks Cruise

This 3-hour, all-inclusive sailing cruise begins with sunset sailing along Chicago's famous skyline, includes optional night swimming, and concludes with a VIP viewing of the Navy Pier fireworks show. Bookings include private boarding at Navy Pier Marina, unlimited snacks and soft drinks, BYOB plus beer, wine and seltzers for purchase, and complimentary ice. Starting at $999, up to 10 guests.

Offer

Sail & Swim Charter

This 4-hour, all-inclusive group sailing adventure includes world-class sailing paired with a private swim and float party aboard a 37' luxury sailboat at the Playpen or a more secluded private anchorage on the Lake. Bookings include unlimited snacks and soft drinks, BYOB plus beer, wine and seltzers for purchase, complimentary ice, access to all floaties and rafts, and fresh towel service. Starting at $1199, up to 12 guests.

Event

Navy Pier Fireworks Cruise

Fri, 21 Aug

A 3-hour, all-inclusive sailing cruise beginning with sunset sailing along Chicago's skyline, with optional night swimming and a VIP viewing of the Navy Pier fireworks show. Bookings include private boarding at Navy Pier Marina, unlimited snacks and soft drinks, BYOB, beer, wine and seltzers for purchase, and complimentary ice. Up to 10 guests. Starting at $999.