At Two Brothers Sailing Adventures Chicago we take great pride in providing a wide selection of sailing adventure options in the Chicago area. Every charter or sailing package we offer has been designed with safe and fun activities that are also environmentally friendly. If you don’t know about Chicago sailing, it is a great getaway in the spring, summer and fall months.

Our safety record is impeccable and our charter captains are fully trained and licensed. We guarantee you’ll have a sailing adventure of a lifetime! Our captains and crew are all accomplished sailors excited to share their love of sailing and the water. With a passion for entertaining new passengers and friends in Chicago, Two Brothers Sailing Adventures is here for you.

We love seeing our friends return year after year! And when you book a Chicago sailing charter adventure with us, you’ll soon see why people love to go ‘sails up’ with Two Brothers Sailing Adventures.

We’re Ready to Put Our Sails Up for You

Two Brothers Sailing Adventures is ready to put our sails up for you. It all starts by tailoring the length of your sail within two to three hours, or more. We provide many options and choices including the sites you’ll sail to and the fare you’ll be treated to during your trip with us. Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan.

Two Brothers Sailing Adventures is a Top 10 Chicago sailing destination. We pride ourselves on offering a wide selection of adventure, including small boat rentals, luxury yacht charters and sailing lessons.

Whether you’re traveling from the Midwest, or across Lake Michigan, Two Brothers Sailing Adventures is the perfect destination for an adventurous sailing getaway in Chicago.

We may be the captain, but when you sail with us, we let you take the helm. Whether you want to sail for two hours or five, sail to see specific sites on Lake Michigan and the Chicago shoreline, or just sit back and enjoy the beautiful views of Lake Michigan at sunrise or sunset, we’re committed to providing you with a unique Chicago sailing experience.


Let’s set sail together and make some great memories!