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    4.9
    (21,955 Reviews)

    Page 8 of 10 • 240 listings

    Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain
    Sailing in Chicago · 6 guests

    Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

    5.0
    $450/hour
    38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!
    Sailing in Chicago · 13 guests

    38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!

    5.0
    $550/hour
    Limited Availability
    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina
    Events in Chicago · 36 guests

    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

    5.0
    $793/hour
    Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
    Sailing in Chicago · 10 guests

    Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

    5.0
    Superowner
    $250/hour
    Instant Book
    Limited Availability
    Polynesian Party Boat for up to 6 people, Captain and Beverage Credit included
    Powerboats in Chicago · 6 guests

    Polynesian Party Boat for up to 6 people, Captain and Beverage Credit included

    New
    $250/hour
    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests
    Sailing in Chicago · 6 guests

    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

    5.0
    $225/hour
    Limited Availability
    Spectacular 55ft Sea Ray 520 Fly Motor Yacht In Chicago
    Events in Chicago · 13 guests

    Spectacular 55ft Sea Ray 520 Fly Motor Yacht In Chicago

    New
    $700/hour
    Limited Availability
    2023 Rio Sport Coupe Motor Yacht Charter Chicago Luxury Cruise
    Events in Chicago · 12 guests

    2023 Rio Sport Coupe Motor Yacht Charter Chicago Luxury Cruise

    New
    $400/hour
    Beautiful 37’ Sea Ray Sundancer Motor Yacht Out of Navy Pier Marina
    Events in Chicago · 6 guests

    Beautiful 37’ Sea Ray Sundancer Motor Yacht Out of Navy Pier Marina

    New
    $400/hour
    High Demand
    62ft Azimut Italian Yacht Charter Chicago for Up to 6 Guests
    Events in Chicago · 6 guests

    62ft Azimut Italian Yacht Charter Chicago for Up to 6 Guests

    5.0
    Superowner
    Best of 2026
    $500/hour
    Instant Book
    65' Sunseeker Manhattan Flybridge Charter on Lake Michigan, Chicago
    Events in Chicago · 13 guests

    65' Sunseeker Manhattan Flybridge Charter on Lake Michigan, Chicago

    New
    $400/hour
    Limited Availability
    Luxury 45’ Catamaran in Chicago | Up to 40 Guests
    Events in Chicago · 40 guests

    Luxury 45’ Catamaran in Chicago | Up to 40 Guests

    New
    Superowner
    Best of 2026
    $900/hour
    Instant Book
    49 Passengers - Chris-Craft Private Yacht - Free Champagne Toast!
    Events in Chicago · 49 guests

    49 Passengers - Chris-Craft Private Yacht - Free Champagne Toast!

    New
    $1,350+/hour
    Limited Availability
    50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina
    Events in Chicago · 24 guests

    50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina

    New
    $1,136/hour
    Instant Book
    Limited Availability
    50ft Azimut Flybridge Yacht at Navy Pier Marina for 13 Guests
    Events in Chicago · 13 guests

    50ft Azimut Flybridge Yacht at Navy Pier Marina for 13 Guests

    5.0
    $350/hour
    31ft Sea Ray Motor Yacht Chicago Romantic Family Getaway!
    Events in Chicago · 6 guests

    31ft Sea Ray Motor Yacht Chicago Romantic Family Getaway!

    5.0
    $350/hour
    Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
    Sailing in Chicago · 6 guests

    Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

    5.0
    $225/hour
    Limited Availability
    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
    Sailing in Chicago · 3 guests

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    4.8
    Snoozed - Active 15 Jul 2026
    Limited Availability
    Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour
    Powerboats in Chicago · 14 guests

    Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour

    5.0
    Superowner
    Best of 2026
    $600/hour
    Premium Sea-Doo Jet Ski Rental – Explore Chicago from the Water
    Water Sports in Chicago · 2 guests

    Premium Sea-Doo Jet Ski Rental – Explore Chicago from the Water

    New
    $150/hour
    Limited Availability
    Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises
    Events in Chicago · 13 guests

    Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises

    5.0
    $750/hour
    High Demand
    Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible SoundSystem!
    Events in Chicago · 12 guests

    Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible SoundSystem!

    5.0
    $350/hour
    Limited Availability
    Luxury Chaparral 277 SSX Wakeboat for 10 Guests In Chicago
    Powerboats in Chicago · 10 guests

    Luxury Chaparral 277 SSX Wakeboat for 10 Guests In Chicago

    5.0
    $175/hour
    Limited Availability
    Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev
    Events in Chicago · 13 guests

    Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

    5.0
    Superowner
    Best of 2026
    $500/hour

    Top Destinations Nearby

    Local Tours Reviews

    1. EJ

      Em

      50ft Azimut Flybridge Yacht at Navy Pier Marina for 13 Guests

      Everything went well, very understanding on the bit of tardiness. The boat itself was excellent along with the area chosen by the boat crew to stay. Very calm waters and just good vibes.

    2. tr

      tzveta

      50ft Azimut Flybridge Yacht at Navy Pier Marina for 13 Guests

      Captain Doug was amazing at making things happen. The crew service and everything was professional and just beyond excellent. My special event was more than memorable. The charters are all so beautiful and clean and offered everything you need for the most comfortable and fun ride. Looking forward to booking again with captain Douglas Charters. I would highly recommend him and his crew to anyone who wants to experience an unforgettable time on the water for any occasion.

    3. JN

      Jessica

      Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

      Such a lovely trip. Up to the trip Kevin and his team were extremely responsive. This was amazing and we will be doing this again! Thanks!

    4. NG

      Nick

      Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour

      My bachelor party had a great time on Troy's boat! The captain was accommodating and the amenities were top notch.

    5. EW

      Evan

      No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

      Incredible time!! Large boat for a large group of people and so fun!!

    6. AW

      Ashley

      Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

      Very responsive and helpful. Great experience!

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