Rent a Boat or Yacht in Chicago, Illinois

Chicago Reviews

1. MC

   Madeline

   450 Sea Ray Sundancer Pure Comfort! We will discount you the GMB Service Fee!

   I highly recommend booking Captain Anthony for your boat day! He is a great host and made sure that our group didn’t have to worry about anything and could just have fun. Our friends are still raving about how much they enjoyed it. Thank you Captain Anthony!

2. SE

   Sabrine

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

   So stunning, and a TON of fun! You get a little tour of Chi and a ton of pic opportunities and then a good amount of time to swim or paddle board. So amazing and definitely will book again!

3. sb

   suzanne

   53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois

   Peter was terrific to work with, and his boat is beautiful - lots of room for everyone to eat and enjoy the water and view. Captain Dean was great, too. Will def book again.

4. JS

   Joelle

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

   This was my first time chartering a boat for the playpen and it was one for the books. Everyone had a blast and the boat was perfect. Thank you Captain Jim for an amazing and safe experience! You were the best!!!!

5. cf

   carolynn

   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 :)

6. RJ

   Rachel

   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!