The Best Boat Rentals in Lake Michigan

2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025

I rented Nilufar's boat along with 11 friends for a six-hour cruise. The boat was a great size with plenty of room for that many people, though it is showing some signs of wear and tear compared to the photos and would have benefited from a pre-cruise interior cleaning. Communication with Nilufar and Captain John from start to finish was fantastic. Captain John and his mate were very professional and always aware of everyone's safety. Overall, a great experience.

Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois

We had the most amazing girls' weekend, and we can't rave enough about our experience! Armand, Captain Matt, and Deckhand Joe were absolutely wonderful to work with. They went above and beyond to make sure everything was perfect for us—from the moment we stepped on the boat until the very end. The boat itself was beautiful, clean, and so comfortable—perfect for relaxing, soaking in the sun, and having a great time on the water. But what truly made the weekend unforgettable was the incredible crew. Captain Matt was professional, friendly, and made us feel safe and at ease the entire time. Deckhand Joe was equally fantastic—helpful, fun, and always making sure we had everything we needed. We’re so grateful for everything they did to make our weekend special. Highly recommend this experience if you're looking for the perfect mix of relaxation, fun, and top-notch service on the water!

Downtown Chicago, Party on the Lake!

It was a wonderful experience from beginning to end! Since before booking and asking for details and accommodations to the day of where I was able to add an additional hour given the schedule and thanks to the seamless communication and outstanding host Ramsey! I would definitely book again with him for future outings. My birthday was perfect thanks to him and a shoutout to Captain Goose!

25ft Rinker - Captained included in price- Chicago

Joe was fantastic to work with and he made sure we had a great time riding around Lake Michigan. We dealt with some spotty weather on the day of our ride, and Joe kept in consistent communication with us and was able to get us going once the weather cleared. Joe took us around to see different spots around the lakeshore, and we were able to park up and enjoy swimming in the lake for a bit along with a few water noodles and floating raft that Joe had. The vibes were great all around and Joe was very easy-going and accommodating for us. If I ever wish to do another boat ride on Lake Michigan, I will be reaching out to Joe.

26 ft. Chaparral SSX257 Luxury Vessel

Mark provided all details and answered all questions super-fast the listing was as described he made the whole process easy and smooth, and Eduard was a great Captain as well. Had an amazing time and will be booking again HIGHLY RECOMMENDED for bookings.

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

Definitely recommend booking with Jason. The booking process and communication leading up to our reservation was top notch. My group had an amazing time and the boat was beautiful! Captain Jimmy was also great and made sure we were taken care of. Looking forward to booking with Jason again in the future.