Great sailboat rentals near Chicago, Illinois.

Sailing Reviews in Chicago

1. CM

   Caley

   Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

   Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

2. MJ

   Meneka

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

   Sailing with Nijole and her husband was an incredible experience! From the start, they were very responsive in communication and flexible with our requested times, even allowing us to extend once on the water. Their knowledge, warmth, and passion for sailing made the trip both safe and fun, with stunning views that we’ll never forget. Highly recommend!

3. ZD

   Zinnia

   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!

4. KM

   Kasey

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

   I booked this experience because Nijole had amazing reviews — and now I truly know why. She is talented, no-nonsense host who knows exactly how to make you feel comfortable when you're aboard. We could not have been more grateful or had a better time. Thank you, Nijole! A superstar.

5. 

   Federica

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

   I was so happy to do this experience but I didn’t know that I was going to like it so much ! I would recommend having this boat for a 2 date or double date ! The owners are really lovely but the best part is going to the pope and sitting there ! Make sure you bring wine, glassware and whatever you want to have ! 2 hours was a perfect time for us! Us we were lucky enough to have of the best sunsets of the season !

6. SN

   Sergey

   Private Cruise onboard Hunter Legend Sailboat in Chicago

   We (myself and 5 of my friends) had a private boat tour with Captain Mitch, and it was a greta experience. We did plenty of swimming in the open lake (outside the harbor) and did a quick tour along the shoreline. Mitch is very knowledgeable about the lake and the city, and many other things - it was both entertaining and educational to chat with him. Highly recommend!