The Best Boat Rentals in Illinois

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

We had a great experience with Captain Z! He and the owner were very accommodating and communication was easy. The boat fit our party of 8. There was a good storage area in the cabin downstairs with a restroom on board. Coolers were provided for our food and beverages. We appreciated that fuel was included in the total cost. We enjoyed cruising around and spending time at the playpen with the beautiful Chicago skyline in the background!

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!

'Genius' 40' Sea Ray Sundancer Captained Charter with all amenities in Chicago!

We had an incredible July 4th charter with Danyelle! Her crew was extremely professional and made sure our group of 12—celebrating a pre-wedding event—was well taken care of. The trip included a beautiful skyline tour followed by relaxing time at the Playpen, with stunning views all around. The photos came out amazing too. Highly recommend and would absolutely book again!

14 Passenger Captained Party & Event Boat in Chicago, Illinois!

Everything about this charter was great! The captain/crew were super friendly and the trip went off without a hitch. It rained for the first hour but the captain and crew kept everything as dry as possible and we still had an awesome trip.

Sail & Swim from a Luxury Sailing Yacht

This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)