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    Illinois, US Boat Rentals & Yacht Charters

    4.9
    (5,631 Reviews)

    Page 3 of 12 • 282 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!
    Events in Chicago · 12 guests

    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!

    4.9
    $250/hour
    Experience Chicago by the water - Rent this 38' Traident Party Pontoon
    Powerboats in Chicago · 20 guests

    Experience Chicago by the water - Rent this 38' Traident Party Pontoon

    5.0
    Superowner
    Best of 2026
    $680/hour
    Diversey Harbor Relax and Enjoy on this 51ft Yacht
    Powerboats in Chicago · 12 guests

    Diversey Harbor Relax and Enjoy on this 51ft Yacht

    5.0
    Superowner
    Best of 2026
    $255/hour
    53' Cruiser Yacht with Flybridge and Sundeck for 11 Guests in Chicago
    Events in Chicago · 12 guests

    53' Cruiser Yacht with Flybridge and Sundeck for 11 Guests in Chicago

    4.9
    Superowner
    $375/hour
    Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests
    Events in Chicago · 13 guests

    Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests

    5.0
    Superowner
    $300+/hour
    Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht
    Events in Chicago · 12 guests

    Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht

    5.0
    Superowner
    Best of 2026
    $350+/hour
    Burnham Harbor, CAPTAIN/FUEL INCLUDED
    Events in Chicago · 7 guests

    Burnham Harbor, CAPTAIN/FUEL INCLUDED

    5.0
    $275/hour
    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests
    Events in Chicago · 12 guests

    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests

    4.9
    $300/hour
    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
    Events in Chicago · 13 guests

    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

    4.9
    Superowner
    $250/hour
    Instant Book
    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina
    Events in Chicago · 13 guests

    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

    5.0
    $300/hour
    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
    Sailing in Chicago · 3 guests

    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    4.8
    $100+/hour
    35' Luxury Motor Yacht Charter in Chicago
    Events in Chicago · 12 guests

    35' Luxury Motor Yacht Charter in Chicago

    4.3
    $180+/hour
    Navy Pier Chicago: Private Sailboat Charter with Captain
    Sailing in Chicago · 10 guests

    Navy Pier Chicago: Private Sailboat Charter with Captain

    5.0
    Superowner
    $250/hour
    Instant Book
    Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!
    Events in Chicago · 12 guests

    Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!

    5.0
    Superowner
    $300+/hour
    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
    SeaRay Sundancer 340 Motor Yacht
    Events in Chicago · 12 guests

    SeaRay Sundancer 340 Motor Yacht

    3.8
    $250/hour
    Private Charter 38' Party Pontoon for up to 20 Guests in Chicago
    Powerboats in Chicago · 20 guests

    Private Charter 38' Party Pontoon for up to 20 Guests in Chicago

    5.0
    Superowner
    Best of 2026
    $700/hour
    Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago
    Events in Chicago · 13 guests

    Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago

    4.9
    Superowner
    $280/hour
    Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago
    Powerboats in Chicago · 6 guests

    Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

    5.0
    $225/hour
    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)
    Events in Chicago · 13 guests

    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    5.0
    Superowner
    $250/hour
    Instant Book
    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!
    Events in Chicago · 13 guests

    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

    5.0
    Superowner
    $350/hour
    Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago
    Events in Chicago · 13 guests

    Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago

    4.8
    $300/hour
    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago
    Events in Chicago · 13 guests

    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago

    4.9
    $400/hour
    37' Spacious Party Yacht For Every Occasion
    Events in Chicago · 12 guests

    37' Spacious Party Yacht For Every Occasion

    5.0
    $225/hour

    Top Destinations Nearby

    Illinois Reviews

    1. LW

      Leteshia

      Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

      WOW! My birthday boating experience couldn’t have been any greater! Starting with him showing up on time and already having everything ready to go for us and everything was soo nice and clean ! The speaker system was amazing, he was very Courteous and had real genuine good vibes! The scenery was EVERYTHING! I would highly recommend booking him ! He even captured some pictures and videos of us and everything turned out PERFECT! Thanks Samuel my birthday has been made 🙂 DEFINITELY BOOK HIM!

    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. CF

      Connie

      45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

      Look no further for your boat rental needs. Captain Douglas will help you choose the perfect boat and crew to make your experience beyond what you can imagine!!

    4. AS

      Ally

      Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht

      Amazing experience, incredibly professional, clean & kind! 10/10 would recommend!

    5. HK

      Hawwa

      Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

      Had an amazing experience with him. He was honestly the best person I’ve rented a boat from and from now on will only be renting from him. He was so easy to work with and so accommodating and caring. 10/10 experience. And I loved the boat as well!!

    6. BM

      Berkeley

      40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests

      Captain T.J was fantastic! We had a great time with her!

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