Windy City Sailing is totally worth the money spent. Edwina and Joe run a tip top operation and adding the Saturday night fireworks into the B&B was OUTSTANDING! A+ Griff D.

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We had wanted to go on an out of town getaway to celebrate our 3rd anniversary, but with our schedules, we couldn't make it work, and then I found Windy City Sailing!!! I wasn't sure what to expect (never chartered a boat before), but the boat was... read more

The people at Windy City Sailing are wonderful not to mention their fantastic yacht. Windy City Sailing is a family run business and they are very proud of the service they offer. they yacht is spotless and very comfortable and the serivce we... read more

Thanks to Windy City Sailing and Josef, I had the most amazing evening of my life. I chose Nebula to be the site of my engagement and between the beautiful boat and the tremendous preparation and hospitality of Josef - including his willingness to... read more

We had an amazing stay on this beautiful sailiboat - a very cool way to experience Chicago. The captain was great- we had the boat to ourselves until the morning sail. So looking forward to our next trip to Chicago...will definitely stay again!

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Joe and Edwina were amazing hosts. Its a family operated business with amazing sailboats. Very romantic, clean and we had all the "alone" time we wanted on the boats. We were a little concerned about how much the owners/captain would be... read more