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Chicago Sailboat Rentals  

  • Starting at $300 Per Hour For Up To Six Guests 

  • Parties Up To Ten Guests Request a Custom Charter Quote Below

  • No Additional Booking Fees

  • Coast Guard Certified Captain Included

  • Depart from Monroe Harbor in Downtown Chicago

  • Complimentary Beverages and Snacks and BYO Alcohol - Catering Available Upon Request

  • Fully Stocked Kitchenware

  • Large Storage Fridge with Ice

  • Private Bathroom and Changing Rooms

  • Stereo Surround Sound Speakers Above and Below Deck with Bluetooth Connection

  • Swim Platform with Ladder, Life-Jackets, Floaties & Towels for Chicago Playpen Parties 

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BOOK A SKYLINE, FIREWORKS, OR PLAYPEN CHARTER BELOW 👇

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  • Chicago Skyline Cruise

    Sailing Cruise along the Chicago Lakefront for up to six guests.
    3 hr
    899 US dollars

  • Playpen Boat Rental

    Half day cruise to the Chicago Playpen for up to six guests.
    4 hr
    1,199 US dollars

  • Fireworks Cruise

    Evening cruise to watch the Navy Pier Fireworks for up to six guests.
    2 hr
    799 US dollars

  • Custom Charter

    Request a custom price quote | 2 hour minimum up to ten guests
    2 hr
    Per group size & hrs

WHAT OUR GUESTS HAVE TO SAY ABOUT US

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We Sail out of Monroe Harbor in Downtown Chicago

CONTACT US WITH YOUR QUESTIONS OR SPECIAL REQUESTS

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02:30 PM

Thank you, we will be in touch!

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