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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,774 Reviews)

    Page 12 of 12 • 287 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    31ft Cabin Cruiser Yacht Charter with USCG Master Captain On Lake Michigan
    Events in Chicago · 6 guests

    31ft Cabin Cruiser Yacht Charter with USCG Master Captain On Lake Michigan

    New
    $300/hour
    Chicago’s Casual Lakefront Escape On 39' Sea Ray Sundancer Yacht - 12 Guests
    Events in Chicago · 12 guests

    Chicago’s Casual Lakefront Escape On 39' Sea Ray Sundancer Yacht - 12 Guests

    New
    $425/hour
    Oceanis 393 Beneteau Sailing Yacht Rental in Chicago
    Sailing in Chicago · 10 guests

    Oceanis 393 Beneteau Sailing Yacht Rental in Chicago

    New
    $275/hour
    Classic 43' Hatteras with Captain included in Chicago
    Events in Chicago · 6 guests

    Classic 43' Hatteras with Captain included in Chicago

    New
    $300+/hour
    Flawless 2024 68ft Sunseeker Manhattan Motor Yacht in Chicago!
    Events in Chicago · 12 guests

    Flawless 2024 68ft Sunseeker Manhattan Motor Yacht in Chicago!

    New
    $1,000+/hour
    Cruise Chicagoland from a Beautiful 44ft Maxum Yacht Ready for Sun And Fun!
    Events in Hammond · 10 guests

    Cruise Chicagoland from a Beautiful 44ft Maxum Yacht Ready for Sun And Fun!

    New
    $400/hour
    Crewed Charter: 47’ Neuville - 20-Passenger Boat! (No Downtown Traffic)
    Powerboats in Hammond · 20 guests

    Crewed Charter: 47’ Neuville - 20-Passenger Boat! (No Downtown Traffic)

    New
    $630/hour
    High Performance Luxury Fountain 43 Center Console for 12 In Chicago
    Powerboats in Chicago · 12 guests

    High Performance Luxury Fountain 43 Center Console for 12 In Chicago

    New
    $775+/hour
    Spacious 37' Rinker Express - Perfect for Lake Michigan Adventures
    Events in Chicago · 8 guests

    Spacious 37' Rinker Express - Perfect for Lake Michigan Adventures

    New
    $250/hour
    Chicago Lake Adventure on 24ft Former Military Willard Marine SeaForce Boat!
    Powerboats in Chicago · 6 guests

    Chicago Lake Adventure on 24ft Former Military Willard Marine SeaForce Boat!

    New
    $270/hour
    Explore the Waves with Ease! Rent Sea Ray Sundancer 320 Yacht today!
    Events in Chicago · 11 guests

    Explore the Waves with Ease! Rent Sea Ray Sundancer 320 Yacht today!

    New
    $225/hour
    Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style
    Events in Chicago · 13 guests

    Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style

    5.0
    $950/hour
    Azimut 62s Motor Yacht In Chicago, Illinois
    Events in Chicago · 12 guests

    Azimut 62s Motor Yacht In Chicago, Illinois

    New
    $1,200/hour
    Sea Ray 460 Sundancer Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    Sea Ray 460 Sundancer Motor Yacht Rental in Chicago, Illinois

    New
    $800/hour
    27' Rinker Fiesta Vee for rent in Chicago - Captained included
    Powerboats in Chicago · 6 guests

    27' Rinker Fiesta Vee for rent in Chicago - Captained included

    4.9
    Superowner
    Snoozed - Active 14 Jul 2026
    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
    Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests
    Events in Chicago · 12 guests

    Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

    3.8
    Snoozed - Active 18 Jul 2026
    Luxury 24' Monterey Private Yacht - Chicago River, Skyline & Playpen Fun
    Powerboats in Chicago · 6 guests

    Luxury 24' Monterey Private Yacht - Chicago River, Skyline & Playpen Fun

    5.0
    Snoozed - Active 15 Jul 2026
    Unique Experience with our Sea Ray 330 Sundancer Yacht for 7 Guests in Chicago
    Powerboats in Chicago · 7 guests

    Unique Experience with our Sea Ray 330 Sundancer Yacht for 7 Guests in Chicago

    5.0
    Snoozed - Active 03 Jul 2026
    Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago
    Events in Chicago · 12 guests

    Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago

    4.9
    Snoozed - Active 25 Jul 2026
    Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht
    Events in Chicago · 10 guests

    Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht

    5.0
    Snoozed - Active 29 Jun 2026
    51ft Sea Ray Sundancer Yacht at Diversey Harbor!
    Events in Chicago · 12 guests

    51ft Sea Ray Sundancer Yacht at Diversey Harbor!

    5.0
    Snoozed - Active 02 Jan 2027
    Sea Ray Express Cruiser 340 Luxury Motor Yacht in Chicagoland
    Events in Hammond · 8 guests

    Sea Ray Express Cruiser 340 Luxury Motor Yacht in Chicagoland

    5.0
    Snoozed - Active 24 Jun 2026

    Top Destinations Nearby

    Chicago Reviews

    1. AD

      Afshan

      Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht

      Amazing experience! Very hospitable service and more than we could imagine! My group and I had an amazing time. Very professional service, very knowledgeable and friendly. Loved it and cannot wait for our next experience with Captain G and team!

    2. KF

      Kyranni

      Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht

      Me an my bridal party had a great time on Captain G’s boat! Captain TJ was an amazing captain and so was the deck hand + deck hand in training. I will definitely be rebooking in the future and I recommend you book too!

    3. CP

      Chandni

      Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht

      Captain G was easy to work with and was a great help during the booking process. His boat was clean and we had a great time during our sunset cruise!

    4. DJ

      Deja

      27' Rinker Fiesta Vee for rent in Chicago - Captained included

      Joe was so nice to talk to and was sohelpful throughout this whole experience. Had everything we needed to make my birthday celebration the best. Got the best photos also!

    5. ML

      Melissa

      27' Rinker Fiesta Vee for rent in Chicago - Captained included

      Joe was great-he kept us on target so we were able to depart in time to head out and was fun to chat with and got us back to dock on schedule. 4 hours flew by. Would book again.

    6. Olivia

      Olivia

      Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style

      Great coordination ahead of time, super convenient to board from the river, beautifully kept vintage boat!

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