Chicago Sailboat and Yacht Charters provide our guests with exclusive, private breathtaking charters that offer complete luxury, flexibility and customization. Take your family on a cruise and experience Chicago like you never thought was possible, a priceless adventure. Charters can range from adventurous blue water sailing past the Chicago Lighthouse, the cribs of Chicago and into the deep blue waters of Lake Michigan or cruising along the lakefront, Navy Pier, the “Playpen”, a trip through the “Locks” and down the Chicago River and taking in some of the best views of Chicago. On Wednesday & Saturday nights we offer Fireworks cruises that take place just off of Navy Pier.

Experience first hand the relaxing beauty of a peaceful sail on our 3+ hour and all day Private boat Charter. We also offer a 3-hour Sunset Cruises, a perfect way to end the day with friends. Our sailing cruises are perfectly equipped to help you celebrate your special occasion; engagement, birthday or anniversary.

We have 2 boats for you to choose from:
Sea Ray 460 – Powerboat
One of the largest domestic express yachts available when she was introduced the Sea Ray 460 Sundancer is an impressive blend of American sport boat styling, luxury-class accommodations, and state-of-the-art construction.

Jeanneau Sun Odyssey 42 DS – Sailboat
The Sun Odyssey 42DS boasts a modern, fluid design, a rare, timeless elegance, and the comfortable interior layout expected of a sailboat built for cruising, all while delivering a superior performance.

Great for:
– Bachelorette or Bachelor Parties
– Birthday Parties
– Corporate events & outings
– Cruises down the river
– Playpen fun day and Tie-ups
– Hanging out at City Winery or other restaurants on the river
– Chicago Air & Water Show

*Additional hours can be purchased.

We can also sail North along the lakefront past Edgewater and all the way up to Bahia Temple in Wilmette on a full day excursion. Lunch, dinner and drink options are available. Our Charters range from 3 hours to a full day. By law we can only take out 6 passengers at a time. Point us where you want to go. We will take you where you want when you want and for as long as you want. Kindly be at the boat at least 15 to 30 minutes prior to your scheduled charter time.Sit back and enjoy a day on the lake. Our boats are in Belmont Harbor please see our directions page for directions to our slip.