Ben's about to hop back across the pond to Ireland, so he's taking this weekend to do some...
k Sailing Classes
Learn to sail quickly, properly, and confidently. Chicago Sailing offers a wide range of instructional programs for beginners to experienced sailors.
S Boat Rentals
Sailors are welcome to rent a sailboat from our 26-boat fleet. There are no membership requirements and rentals are booked by the hour from dawn to dusk.
A special event or trip to Chicago isn't complete without a sailing excursion along Lake Michigan. Our vessels can accommodate groups from 2 - 80, with a captain to guide your journey.
Latest from our Blog
Apologies all, I was busy this morning doing a corporate team building event, and I eventually got...
aka A Cautionary Tale If you have ever rented or taken lessons at Chicago Sailing, you have...
Great staff and sailing classes. Jim my teacher is da man! 2 weekend class and you can rent a sail boat from them without joining some snooty club like process. Chill crew overall and hesitant to give them 5 stars only because I like the fact that are Chicago's best kept secret :) don't want too many people taking my slot for renting on the weekend! :)
This was really cool. Great for working together and having fun. It easily facilitated participants getting to know each other and they learned something about sailing in the process.
I learned so much and had a great time. Thanks for everything! Enjoy the rest of your summer and good luck with sailing in the coming year.