The Best Boat Rentals in Illinois

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!

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 :)

50' Multi-level Luxury Yacht with Party up to 12

Captain Jim and his team went above and beyond to make our charter an unforgettable experience. From the moment we departed to the smooth arrival back at the dock, everything was handled with professionalism, confidence, and a warm, friendly attitude. The boat was immaculate, the ride was smooth, and Captain Jim clearly knew the waters like the back of their hand. They made us feel safe, relaxed, and completely taken care of the entire time. Whether it was pointing out interesting sights, adjusting course for the best views, or making sure we had everything we needed on board, their attention to detail was exceptional. You can tell they truly love what they do—and it shows in the way they connect with guests and manage every aspect of the trip seamlessly. I highly recommend Captain Jim and his team, to anyone looking for a top-tier charter experience. Thank you again for an incredible day on the water!

25ft Rinker - Captained included in price- Chicago

Joe was incredible! I booked a 2 hour skyline cruise/swim time for my nephew's 8th birthday and Joe made us so comfortable. He answered all my questions about life jacket sizes and weather fluctations and adjusted our departure time to ensure we didn't get caught in a storm. Highly recommend!

Private Cruise onboard Hunter Legend Sailboat in Chicago

We had an amazing time sailing around Lake Michigan with Captain Mitch! The marina was super easy to locate/get to, the boat was the perfect size for our group of four, and we really enjoyed our time on the water. I would highly recommend booking a trip with 3rd Coast!