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    4.9
    (28,373 Reviews)

    Page 3 of 10 • 240 listings

    Multi Level 48' Carver Mariner Yacht for 13 Guests in Chicago, IL
    Events in Chicago · 13 guests

    Multi Level 48' Carver Mariner Yacht for 13 Guests in Chicago, IL

    5.0
    $350/hour
    Limited Availability
    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago
    Events in Chicago · 12 guests

    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago

    5.0
    $275/hour
    Limited Availability
    "Captain is Free". If you have 6 passengers or less...this yacht is Just Right!!
    Events in Chicago · 6 guests

    "Captain is Free". If you have 6 passengers or less...this yacht is Just Right!!

    5.0
    $350+/hour
    Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago
    Events in Chicago · 13 guests

    Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago

    5.0
    Superowner
    Best of 2026
    $225+/hour
    Lake Michigan Adventure on 33ft Sea Ray Sundancer Motor Yacht
    Events in Chicago · 10 guests

    Lake Michigan Adventure on 33ft Sea Ray Sundancer Motor Yacht

    New
    $275/hour
    Limited Availability
    44ft Regal Commodore Motor Yacht Charter In Chicago
    Events in Chicago · 13 guests

    44ft Regal Commodore Motor Yacht Charter In Chicago

    5.0
    $275/hour
    Limited Availability
    38ft 'The Gwen' Carver Mariner Captained Charter With All Amenities In Chicago!
    Events in Chicago · 13 guests

    38ft 'The Gwen' Carver Mariner Captained Charter With All Amenities In Chicago!

    4.9
    Superowner
    $275/hour
    Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!
    Events in Chicago · 10 guests

    Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!

    New
    $300+/hour
    Limited Availability
    Spacious 50’ Cruiser Yacht with Swim platform
    Events in Chicago · 12 guests

    Spacious 50’ Cruiser Yacht with Swim platform

    5.0
    $400+/hour
    Limited Availability
    44' Luxury Sea Ray Express Yacht Rental/Party Boat with Captain in Chicago
    Events in Chicago · 13 guests

    44' Luxury Sea Ray Express Yacht Rental/Party Boat with Captain in Chicago

    4.9
    $349/hour
    Limited Availability
    60ft Azimut Evolution Double Decker Yacht Charter in Chicago
    Events in Chicago · 13 guests

    60ft Azimut Evolution Double Decker Yacht Charter in Chicago

    5.0
    Superowner
    Best of 2026
    $750+/hour
    50ft Double Deck Yacht "Liquid Asset 3" in Chicago!
    Events in Chicago · 13 guests

    50ft Double Deck Yacht "Liquid Asset 3" in Chicago!

    New
    Superowner
    Best of 2026
    $300/hour
    Limited Availability
    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion
    Events in Chicago · 12 guests

    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

    5.0
    $250/hour
    Summertime Chi Ready! Rent this Carver 38 Santego Motor Yacht for 12 Guests
    Events in Chicago · 12 guests

    Summertime Chi Ready! Rent this Carver 38 Santego Motor Yacht for 12 Guests

    5.0
    $325/hour
    High Demand
    New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago
    Events in Chicago · 12 guests

    New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago

    5.0
    Superowner
    $400/hour
    Limited Availability
    Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago
    Events in Chicago · 8 guests

    Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

    4.8
    $300/hour
    Limited Availability
    Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht
    Events in Chicago · 10 guests

    Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht

    5.0
    $275/hour
    High Demand
    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
    Limited Availability
    Luxury 54' Sea Ray Sundancer Yacht for Charter in Chicago
    Events in Chicago · 12 guests

    Luxury 54' Sea Ray Sundancer Yacht for Charter in Chicago

    5.0
    $500/hour
    Limited Availability
    Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!
    Events in Chicago · 12 guests

    Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!

    4.9
    $250/hour
    Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht
    Powerboats in Chicago · 12 guests

    Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht

    4.9
    Superowner
    $300/hour
    Limited Availability
    63ft Premier Sea Ray Sundancer Yacht Perfect for Chicago Playpen, River, Winery
    Events in Chicago · 12 guests

    63ft Premier Sea Ray Sundancer Yacht Perfect for Chicago Playpen, River, Winery

    5.0
    Superowner
    $700/hour
    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL
    Events in Chicago · 13 guests

    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL

    New
    $1,089/hour
    40' Cruisers Yachts "Bad Boys II" for rent in Chicago
    Events in Chicago · 13 guests

    40' Cruisers Yachts "Bad Boys II" for rent in Chicago

    New
    $818/hour

    Top Destinations Nearby

    Local Motor Yacht Reviews

    1. AF

      Adekunle

      60ft Azimut Evolution Double Decker Yacht Charter in Chicago

      Chris is very responsive and transparent. This listing is super spacious, modern, and clean. My group had an amazing time during our charter and I would recommend anyone considering a charter with Chris to go ahead.

    2. CS

      Cecil

      60ft Azimut Evolution Double Decker Yacht Charter in Chicago

      This is an amazing vote, all of the captains that partner with Chris are amazing, especially Kyle and Josh. So thankful for them for providing us a great experience! Will definitely book with them again!

    3. MF

      Madalyn

      42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

      I had a great experience and we had an absolutely beautiful time for my sister‘s bachelorette! The captain was great!

    4. AL

      Anneliese

      42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

      We had the best time on the boat! Just as advertised and our captain was great.

    5. Khalia

      Khalia

      Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!

      Loved the boat had a great experience very fast response and accommodated all our needs

    6. Ukachi

      Ukachi

      38ft 'The Gwen' Carver Mariner Captained Charter With All Amenities In Chicago!

      Great service and excellent ride. Thanks captain james for everything !

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