Experience the thrill of Memorial Day Weekend in Chicago, where the summer season kicks off with a bang on May 1st, officially marking the start of the city’s boating scene. Embrace the warm-weather festivities from the best seat in the house—your own private boat or yacht at The PlayPen. Whether you’re savoring the sun on deck, taking in breathtaking skyline views, or hosting a celebratory gathering with friends, renting a vessel lets you immerse yourself in Chicago’s vibrant atmosphere while enjoying the comfort and luxury of a personal retreat. Start your summer in style and make unforgettable memories by setting sail with The PlayPen this Memorial Day Weekend.
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Sunday, May 25, 2025 at 10:00 PM
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The Chicago Playpen is a unique spot situated off the coast of Chicago, nestled between the historic Navy Pier and the tranquil Oak Street Beach. But what makes the Playpen stand out is the striking contrast it presents. On one side, you have the serenity of the vast expanse of Lake Michigan, teeming with a variety of boats and yachts, while on the other, you have the dynamic cityscape of Chicago. The magnificent city skyline serves as a dramatic backdrop to the myriad of vessels at the Playpen, making for some captivating visuals.