Chicago, Illinois Boat Rentals & Yacht Charters

Chicago Reviews

1. HK

   Hawwa

   Beautiful Four Winns 225 Sundowner Boat w/Big Sound System

   Had an amazing experience with him. He was honestly the best person I’ve rented a boat from and from now on will only be renting from him. He was so easy to work with and so accommodating and caring. 10/10 experience. And I loved the boat as well!!

2. M

   Mark

   Up to 7 person Private Sailing Catamaran Charter with Captain included

   Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

3. S

   Sandra

   Up to 7 person Private Sailing Catamaran Charter with Captain included

   Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

4. J

   Jeff

   Up to 7 person Private Sailing Catamaran Charter with Captain included

   What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

5. 

   David

   39' SeaRay Sundancer for 11 Guests – 3 Boats! Weekday Discount!

   Capt John and his boats/deckhands/captains are all great! Very easy to communicate with and get all the insights you want. We had 2 families with 5 kids overall and it was a great trip. We booked on Chicago Scene day and we were able to see some of the fun, but we also stayed further away from the main playpen. Capt had to dock up once to let off some family members early on the trip and it was seamless. The Sundancer is in great condition and a lot of fun to be on. Highly recommend.

6. SD

   Shreerupa

   44FT Regal Commodore

   Robert was fantastic. He was very prompt with his communication. The boat was very clean and had plenty of seats and space to accommodate our group of 13. Our primary goal was watching the Air & Water show which was running late. Robert was kind enough to give us extra time for free so that we had the best experience and did not miss the main attraction of the show.