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We’ve designed coverage to handle damages, so you can focus on the adventure.The cost to rent a boat in Chicago starts at $100 per hour, depending on the amount of time that you would like to use the boat.
With a Chicago boat rental, top destinations include the Chicago River for stunning views of the city's iconic architecture and skyline. Lake Michigan offers a chance to anchor near Navy Pier or the lively Playpen area for sunbathing and socializing. North Avenue Beach and Montrose Beach are popular spots for swimming and relaxing just offshore. For a quieter cruise, head to Belmont or Burnham Harbor near Museum Campus. Each destination offers a unique way to experience Chicago from the water.
Black Yacht Weekend is a floating boat party on Lake Michigan against the stuning Chicago skyline. In 2025, Black Yacht Weekend is happening from Thu, June 19 to Sun, June 22.
Chicago Scene Boat Party is an annual boat event on Lake Michigan. In 2025, Chicago Scene Boat Party is happening Fri, Jul 25 to Sun, Jul, 27 at The Playpen.
Belmont Harbor → North-side beaches and parks; lakefront neighborhoods; beaches like Montrose Beach (northward) or moving south along the lakefront into downtown as you cruise. Approximately 15-20 minutes cruise to playpen area depending on conditions and route
Burnham Harbor → South-lakefront destinations, Museum Campus area, near Soldier Field / McCormick Place; good for a longer cruise along the lakefront down south or up toward downtown. Approximately 10-15 minutes cruise to playpen area depending on conditions and route
Montrose Harbor → Montrose Beach, Montrose Point / Bird Sanctuary / North-side lakefront — ideal for a more relaxed, “local beach + harbor” experience; Approximately 20-30 minutes cruise to playpen area depending on conditions and route
Navy Pier Marina → Downtown lakefront, skyline cruises, quick access to beaches and the central “Playpen” area, easy city-side walkable access to hotels/restaurants/entertainment. Approximately 5-10 minutes cruise to playpen area depending on conditions and route
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Boating around Chicago is all about contrast—open lake cruising paired with up-close city views. Start with a ride along Lake Michigan for wide-open water and skyline views, or head into the Chicago River for a more immersive look at the city. On warm days, locals anchor at the Chicago Playpen to swim and relax just offshore. With Boatsetter, you can find the right boat for your plans or go out with a licensed captain—making it easy to settle in, take in the views, and enjoy Chicago from a whole new perspective.
Cruise along Lake Michigan for sweeping views of the skyline and landmarks like Navy Pier. It’s one of the most iconic ways to experience Chicago from the water.
One of the most popular boating spots in Chicago is the Chicago Playpen, where boaters gather to anchor, swim, and enjoy a lively summer scene just off the city’s shoreline.
Head into the Chicago River for a slower-paced cruise through the heart of downtown, passing under bridges and alongside some of the city’s most famous architecture.
