Anchor & Swim

Anchoring and swimming in Lake Michigan around Chicago is one of the Midwest’s best-kept summer luxuries—fresh water, skyline views, and calm, clear anchorages that rival coastal boating destinations.

The Playpen (Chicago)

Anchoring at The Playpen is the iconic Chicago boating experience. Located just off Navy Pier, this protected anchorage fills with yachts, cruisers, and charters all summer long. Boats raft together, music drifts across the water, and swimmers jump in with the Chicago skyline as their backdrop. The water here is surprisingly clear on calm days, making it perfect for floating, social swimming, and soaking up the energy of the city. It’s lively, social, and unmistakably Chicago.

Monroe Harbor

Just south of the Playpen, Monroe Harbor offers a more relaxed anchoring and swimming experience. With views of Grant Park, Buckingham Fountain, and downtown high-rises, Monroe is ideal for guests who want to swim without the party atmosphere. The harbor provides calmer water, making it great for first-time Lake Michigan swimmers or families looking for a peaceful, scenic stop.

Wilmette Harbor & North Shore Anchorages

Heading north, Wilmette Harbor and nearby North Shore anchor spots feel quieter and more refined. Here, the lake often takes on a deeper blue tone, and the shoreline greenery replaces skyscrapers. Anchoring in this area is perfect for long swims, paddleboarding, and enjoying Lake Michigan’s natural beauty without the downtown crowds. It’s a favorite for boaters seeking a serene, upscale vibe.

St. Joseph, Michigan

Across the lake, St. Joseph, Michigan is a popular destination for longer charters and overnight trips. Known for its sandy beaches, dunes, and charming harbor town, anchoring near St. Joseph offers some of the clearest swimming water on Lake Michigan. The freshwater feels crisp and refreshing, especially on hot summer days, and the sunsets over the Michigan shoreline are unforgettable.

Bonus Destination: Hammond & Indiana Dunes

Just south of Chicago, the Indiana Dunes area provides a surprisingly scenic anchoring option. With rolling sand dunes and wide open beaches, this destination feels remote and peaceful while still being close to the city. It’s a great spot for swimming, floating, and enjoying Lake Michigan in a more natural setting.

Why Lake Michigan Swimming Is So Special

Unlike saltwater destinations, Lake Michigan is fresh, clean, and gentle on the skin, with no tides or marine life concerns. On calm days, visibility can be excellent, and the cool water offers the perfect refresh during Chicago’s warm summer months. Whether you’re anchored in the heart of downtown or off a quiet shoreline, swimming in Lake Michigan feels both invigorating and indulgent.

From high-energy afternoons at The Playpen to peaceful swims near Wilmette or scenic getaways to Michigan, anchoring and swimming in Lake Michigan around Chicago delivers a luxury boating experience that’s uniquely Midwest—and completely unforgettable.