Great sailboat rentals near Chicago, Illinois.

Sailing Reviews in Chicago

1. 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!

2. 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!

3. SB

   Sean

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

   Excellent experience all around. Our excursion was a great mix of swimming and peaceful cruising under sail. Nijole was a great captain and created a wonderful experience for a family afternoon on the water.

4. SG

   Stephanie

   Special End of Season Sunday pricing for 8 to 13 passengers

   My friends and I rented Captain Russell’s boat for a wedding weekend celebration and had the best time! The boat was beautiful, and Captain Brian made the whole experience super enjoyable. Highly recommend!

5. JM

   Julie

   No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

   Great vessel. Everything we needed! Amazing deck hand and Captain (Georgia and Matt). They made our air and water show experience incredible!

6. 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!