Went here for a sunset sail with my boyfriend. Really Enjoyed being able to go on a sail boat. They let volunteers from the crowd pull open the sails. Staff is friendly and funny. read more

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Windy City Sailing always exceeds expectations. My family and I look forward to our annual sailing trip w/ Captain Joe and his crew. Even just unplugging on a three hour tour beats some week long vacations we've taken in terms of the chill factor. Our family and friends pretty much compete every year to be the lucky ones who get invited to join us. Our favorite one is the Air & Water Show. Can't wait for this year's trip. read more

Just booked a 3 hour cruise on their 39' foot boat, and had a blast. Booking was professional and easy and the captain and deckhand were friendly, entertaining and professional. The boat was immaculately kept, and neat - both on deck and below. Plenty of space for 8 big guys. Cancellation policy / reservations were a huge plus - they will REFUND your money in the event of a major storm. We were lucky enough to get out after some rain, and it was perfect! read more

I chartered with Windy City Sailing for a noon-time cruise for my wife and me to help celebrate our 30th anniversary. We sailed on a 40 foot motor cruiser, the Jolly Mon, captained by Gentre. We were lucky that the day was calm and cruising was smooth. In addition to the comfort of the cruiser, Captain Gentre was great! His knowledge of the Chicago coastline, and all things Lake Michigan made for an enjoyable and informative experience. We were treated to both great skyline views as well as close ups such as the Buckingham Fountain going off, the museum campus and Navy Pier. We also viewed racing catamarans that were practicing turns around a buoy, as part of a program to build interest in bringing the America's Cup to Lake Michigan. Again, we could not have asked for a better experience, nor a more knowledgeable, competent and friendly captain than Gentre! read more

Yare vessels and as salty a crew as you'll find in fresh water. A real Chicago experience.

Thank you so much for a great sail! Edwina was amazing to work with on logistics in advance of our sail and Captain Marty and crew were so accommodating the day of! We appreciate your efforts to make my 30th birthday a special one! read more

We had an amazing time on the Nebula! The weather was perfect and Captain Mike and Lori were terrific we didn't have to lift a finger! We sailed to Northly Island for a concert and is was great listening to the Barenaked Ladies as we swam in the lake. We definitely will sail again! Thank you Windy City Sailing! read more

We used WCS late last summer for a Saturday evening cruise. From booking the event to docking at the harbor Joe and crew were awesome. Very easy going and polite. You don't even know they are there but they'll tell you anything you need to know about sailing and the lake. They really create a very relaxing atmosphere. You feel like it's your boat. They can offer overnight stays if you wish and have catering recommendations. We packed a couple coolers and brought our own stuff. It's a great experience and you are in very good hands. We look forward to doing again this summer. read more

We took 4 people out for the Air and Water Show on 8/15/15. It was fantastic! Our group of 4 has decided to make it an annual tradition. Jessica was an incredibly kind and helpful captain. She made us feel like the boat was ours for the day. I would book with Windy City Sailing again in a heartbeat. Overall they are a very professional company company with wonderful employees. read more

Had a great time sailing last weekend....boat was beautiful...clean and looks brand new. The captain was informative and gave us great insights into the city skyline. My whole group had such fun...we will return soon. Thank you Windy City Sailing....I felt like I was on vacation!! read more

I found it very easy to book a sail and had only pleasant communications with the staff. My friends and I enjoyed a perfect afternoon on Lake Michigan, complete with beautiful views of Chicago. read more

We took 6 people out for a sunset cruise on Lake Michigan and had a wonderful time. The entire experience from planning with Edwina to sailing with Capt. Marty was super easy and friendly. We brought our own food and drinks with us, and were able to prepare them in the kitchen in the cabin. I was very pleasantly surprised that the boat had 2 functioning toilets! As we sailed out from Belmont Harbor, with the small motor running we got comfortable on the boat. Once out of the Harbor Capt. Marty cut the motor and put up the mainsail and we were sailing! We topped 6 knots (very comfortable) and had a really great time. As the sun was setting we came back to the Harbor. I highly recommend Windy City Sailing for any type of chartered sailing adventure. read more