Rent a boat in Chicago

We have sailboats, power boats, and BIG BOAT available. Charter a sailboat in Chicago for up to 11 people, Rent a power boat in Chicago for up to 12 people, charter BIG BOAT for up to 36 people.

Click here to check pricing and availability on any given day and time. You can not only see availability and all the standard options, but also book online if you are ready to make a reservation. Feel free to call us at 773-236-7245 with any questions that you need answered, or if you prefer the personal service instead of booking online.

Captains (when you rent a boat in Chicago)

All our rental boats will have licensed local Chicago captains on board for the charter. Sometimes we are allowed to assign them, other times you have to choose one from a pre-vetted list (USCG regulations) depending on the type of charter. Either way, we make the process simple.

Types of Boats and Charters in Chicago

Come out for in the daytime for a cruise, and even a swim in the playpen or south Monroe harbor. Rent a boat in Chicago at night for an even more beautiful view of the historic Chicago skyline.

Power Boat Rentals for up to 12 people — Power Boats – up to 12 people. These are perfect for a trip to swim and a skyline cruise. On less busy days, a trip on the river can is amazing.

Rent our party boat, Big Boat, a 36 passenger party boat — BIG BOAT – up to 36 passengers for the ultimate party boat. Tons of space both under the sun and under cover. Drink packages are available as well on BIG BOAT. Charter this boat and your large group will have the perfect venue for any get together.

Luxury Yacht rental in chicago — Sailboats – up to 11 people offer the view of the skyline on a peaceful sail. If you plan for it on a longer sail, you can also have you r captain anchor down and swim in the breakwater protected area of the playpen.