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Chicago Sailboat and Yacht Charters offers exclusive, private breathtaking charters that provide complete luxury, flexibility, and customization. Our charters take you on a journey through the deep blue waters of Lake Michigan, past the Chicago Lighthouse, and along the lakefront, Navy Pier, and the "Playpen". With our two beautiful powerboats, we can accommodate up to 25 guests and offer a "Tie-Up in the Playpen" just off Lakeshore Chicago. Whether you're looking for an adventurous blue water sailing experience or a relaxing cruise, we've got you covered.