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    4.9
    (21,954 Reviews)

    Page 3 of 10 • 240 listings

    Your Private 50ft Sea Ray Luxury Yacht Escape in Chicago
    Events in Chicago · 12 guests

    Your Private 50ft Sea Ray Luxury Yacht Escape in Chicago

    New
    $450+/hour
    Limited Availability
    Luxury 40ft Maxum 3700 SCR Motor Yacht Available To Cruise To The Playpen!
    Events in Chicago · 12 guests

    Luxury 40ft Maxum 3700 SCR Motor Yacht Available To Cruise To The Playpen!

    4.8
    $275/hour
    Limited Availability
    44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain
    Events in Chicago · 13 guests

    44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain

    4.8
    $349/hour
    Limited Availability
    42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!
    Events in Chicago · 12 guests

    42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!

    5.0
    $350/hour
    High Demand
    Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain
    Powerboats in Chicago · 8 guests

    Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain

    4.4
    $250/hour
    High Demand
    Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!
    Powerboats in Chicago · 10 guests

    Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!

    5.0
    $250/hour
    High Demand
    39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
    Events in Chicago · 12 guests

    39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

    5.0
    Superowner
    Best of 2026
    $350+/hour
    Limited Availability
    55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand
    Events in Chicago · 12 guests

    55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

    5.0
    $375+/hour
    50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo
    Events in Chicago · 13 guests

    50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo

    5.0
    $375/hour
    Limited Availability
    Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht
    Events in Chicago · 12 guests

    Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht

    5.0
    Superowner
    Best of 2026
    $450/hour
    Instant Book
    Limited Availability
    Enjoy the Sun on Lake Michigan with Family or Friends on a 58' Sea Ray Yacht
    Events in Chicago · 12 guests

    Enjoy the Sun on Lake Michigan with Family or Friends on a 58' Sea Ray Yacht

    5.0
    $375/hour
    Limited Availability
    Set Sail on a Spacious 42' Silverton Express Cruiser Yacht
    Powerboats in Chicago · 12 guests

    Set Sail on a Spacious 42' Silverton Express Cruiser Yacht

    5.0
    $275/hour
    High Demand
    Stunning 105ft Denison Party Yacht in Chicago
    Events in Chicago · 30 guests

    Stunning 105ft Denison Party Yacht in Chicago

    4.7
    $1,450+/hour
    Limited Availability
    Maxum 44ft Motor Yacht "My Kinda Party"
    Powerboats in Chicago · 13 guests

    Maxum 44ft Motor Yacht "My Kinda Party"

    4.9
    Superowner
    Best of 2026
    $260+/hour
    Limited Availability
    Rent this 42ft Regal Commodore Express Cruiser In Chicago
    Powerboats in Chicago · 13 guests

    Rent this 42ft Regal Commodore Express Cruiser In Chicago

    5.0
    Superowner
    Best of 2026
    $225+/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
    High Demand
    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
    High Demand
    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
    $325/hour
    High Demand
    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
    High Demand
    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

    Top Destinations Nearby

    Local Tours Reviews

    1. LP

      Lijana

      55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

      We rented this boat for our 30th anniversary and it was better than we hoped! How lucky we were to find Robert B. His boat is beautiful, very clean, perfect for the party of 12 people. And he was so nice to give us the parking pass to be dropped right next to the boat. Thank you so much! We highly recommend this vessel to anybody who wants to have a great time! Lijana and Peter Paulettti ❤️❤️❤️

    2. AL

      Ashley

      Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht

      We had an amazing time. Captain Eric was great. The family really enjoyed the sights and the boat is beautiful! It is nice that there are multiple different spaces onboard to enjoy indoor and outdoor.

    3. BH

      Benjamin

      55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

      Robert was friendly and communicative. He put me in touch with a captain (Jamie) who added to the experience. Great boat. No complaints.

    4. Cindy

      Cindy

      Maxum 44ft Motor Yacht "My Kinda Party"

      Had an amazing birthday weekend with my friends for my birthday, Captin Drake was great and I would definitely book again! Thank you for an amazing experience.

    5. LM

      Lindsey

      Rent this 42ft Regal Commodore Express Cruiser In Chicago

      Amazing boat and trip. No notes really.

    6. BF

      Brittany

      55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

      Wonderful ride today!

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