Learning to sail is fast, easy, and fun at Chicago Sailing. You will become an accomplished, confident skipper in just a few sessions of on-the-water training. Our classes are comprehensive and certified to the highest standard in the industry, those of US Sailing. We also have the largest fleet of training vessels in the greater Midwest, meaning that we offer the most opportunities for on-the-water training. Soon you will be joining the thousands of sailors who have launched their sailing adventure at Chicago Sailing.