Book Now  Specials
"BIG BOAT" - up to 36 people         Work for CSC
REWARDS         Pricing / Availability

Sailing in Chicago

The Chicago skyline is a spectacular sight from a sailboat. Whether you are sailing towards Navy Pier, or straight out away from the Chicago shoreline, the views cannot be matched.

Fireworks Sailing

Sailing to Navy Pier to see the Fireworks will offer a fantastic front row view of the show. The Chicago skyline acts as a backdrop and it seems as if the fireworks are directly overhead.

Night Sailing

Sailing as the sun sets behind the Chicago skyline and watching the glow come up from behind the buildings after sunset is followed by seeing the skyline light up once the sky gets completely dark.

Swimming/Sunning Sails

Enjoying a swim party or just a quick dip anchored down at the “playpen” or further off shore is a great way to spend part of your sail on a hot summer day.

Chicago Sailboat Charters

Chicago Sailboat Charters provides the best variety, service, and value for any sailing experience you desire. With many sailboats to choose from, we can arrange the perfect sail to meet your wishes and fit your budget. Whether you are looking for a romantic sailing trip for two, or a sailboat for up to ten people, we are open every day of the week and will be sailing any time you wish from early in the morning until late at night.