"BIG BOAT" - up to 36 people
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.
Daytime-Sailing
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.
Navy Pier Fireworks Sailing
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.
Night Sailing
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.
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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

Charter a boat in Chicago with us. When you rent a boat from Chicago Sailboat Charters, we provide the best variety, service, and value for any charter or rental boat experience you desire. With several sailboats and power boats, as well as our 36 passenger Big Boat, 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, a sailboat for up to 11 people, power boat rental for up to 12 people, or a party boat rental for up to 36, we are open every day of the week and we are on the water from early in the morning until late at night. If you are looking for a Chicago boat rental with captain, we are the charter boat company or you.