Top Rated Private Boat Charters from $300

38 ft
Boat length
Up to 6
This boat is rented with a captain
Owner’s response rate

The boat

ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs.

While on board you can watch the sun set behind Chicago's skyline or watch a full moon rise out of Lake Michigan. You can also experience the Wednesday and Saturday Navy Pier Fireworks from the front row. Want to host your corporate outing? We can do it. Want to propose to your partner on a sailboat? Perfect! The annual Air and Water Show as well as Museum Campus, Northerly Island, and Soldier Field events are some other opportunities to experience the water. Or, maybe just sail with us because it's your Sunday Funday or you're on a staycation!

Whether it's your first time, only time, or just the next time; we want your sailing experience with us to be the best time you have this Summer.

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Captain Conway
Owned by
Captain Conway


Stereo Aux Input
Bluetooth audio
Cooler / Ice chest
Air conditioning
Swim ladder
Children's life jackets
Depth finder
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38 ft.
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/ (excl. fees)
Start time
You won't be charged yet

Ratings & reviews

Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
Captain Conway
Captain Conway
The owner and master is a professional mariner with over 15 years of experience as a licensed USCG Master Captain. Their career has taken them from the Gulf of Mexico to Boston Harbor to the Willamette River to the San Juan Islands and Lake Michigan ever since 2010. They have commanded vessels from 8' to 148' and everything in between.
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  • Response rate: 54%
  • Avg. response time: < 48 hours

Things to know

Allowed on boat

kids under 12
glass bottles

  • Free cancellations until 5 days before the booking start date.
  • 50% refund for cancellations between 2-5 days before the booking start date.
  • Cancellations within 2 days of the booking start date are non-refundable.
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This boat belongs to a Commercial Owner, an independent boat rental company. A Commercial Owner is an independent, Boatsetter-approved boat rental company who provides their own insurance to their guests.

A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.

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If requested, the owner can provide a list of available captains for bareboat charter or the renter can use their own qualified captain. If the boat is being time chartered, the owner will provide the Captain.