Great sailboat rentals near Chicago, Illinois.

Sailing Reviews in Chicago

1. WK

   William

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

   Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!

2. AA

   ADOLFO

   Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

   This was an amazing boat! It’s HUGE!! Captain Lester was a true professional who catered to all are requests. This was the best day of our summer. I would highly recommend this boat! Truly great!

3. 

   Aisat

   38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!

   Captain Russell & his team were so nice and helpful and accommodating and the vessel was perfect for a group of 10-12. We had the right vibes and experience and would highly recommend!

4. 

   Eric

   Sailing Lessons with Chicago's #1 Rated Sailing School

   I had a four hour private lesson with Doug and small crew. All were very helpful and knowledgeable, it was a great learning experience. I look forward to joining them again.

5. 

   Erica

   Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

   Ben is wonderful he is so passionate and knowledgeable about sailing and he made it a great time.

6. JD

   Jorge

   No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

   Captain Dennis and Kate were great hosts. Everything was perfect