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 just off of Navy Pier. Our Boats: We offer two beautiful powerboats to choose from. We have a Searay Sundancer 51′ and a Searay Sundancer 35′ cruiser. Between both boats, we can take out a total of 25 guests and do a “Tie-Up in the Playpen” just off Lakeshore