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    4.9
    (21,785 Reviews)

    Page 6 of 10 • 240 listings

    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
    Instant Book
    Limited Availability
    Private Boat Charter - Sea Ray 390 Sundancer In Chicago
    Events in Chicago · 12 guests

    Private Boat Charter - Sea Ray 390 Sundancer In Chicago

    New
    $500/hour
    High Demand
    Party Cruise on 40ft Sea Ray Express Yacht Chicago for You & 12 Friends
    Events in Chicago · 12 guests

    Party Cruise on 40ft Sea Ray Express Yacht Chicago for You & 12 Friends

    New
    $300+/hour
    Limited Availability
    2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

    4.7
    $400/hour
    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
    Limited Availability
    Cruisers Y3375 Express Yacht Downtown Chicago Experience
    Powerboats in Chicago · 10 guests

    Cruisers Y3375 Express Yacht Downtown Chicago Experience

    5.0
    Superowner
    $250/hour
    High Demand
    Take in Breathtaking Chicago Skyline Views from Spacious 32' Chaparral Yacht
    Events in Chicago · 12 guests

    Take in Breathtaking Chicago Skyline Views from Spacious 32' Chaparral Yacht

    New
    $450/hour
    Limited Availability
    40ft Carver Mariner Motor Yacht Charter in Chicago
    Events in Chicago · 13 guests

    40ft Carver Mariner Motor Yacht Charter in Chicago

    New
    $745/hour
    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
    Limited Availability
    Exquisite Mediterranean 40' with Flybridge Yacht in Chicago
    Events in Chicago · 12 guests

    Exquisite Mediterranean 40' with Flybridge Yacht in Chicago

    5.0
    $400/hour
    Limited Availability
    Private Luxury Charter In Chicago - Sea Ray 360 Sundancer Motor Yacht
    Events in Chicago · 13 guests

    Private Luxury Charter In Chicago - Sea Ray 360 Sundancer Motor Yacht

    5.0
    $300/hour
    High Demand
    39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included
    Events in Chicago · 12 guests

    39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included

    5.0
    $350+/hour
    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests
    Events in Chicago · 12 guests

    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests

    New
    $300/hour
    32' Maxum 3000 SCR Motor Yacht on Lake Michigan, Chicago
    Events in Chicago · 10 guests

    32' Maxum 3000 SCR Motor Yacht on Lake Michigan, Chicago

    5.0
    $300/hour
    Limited Availability
    Captained Charter on 36' Sea Ray Cruiser in Chicago
    Events in Chicago · 12 guests

    Captained Charter on 36' Sea Ray Cruiser in Chicago

    4.8
    $350/hour
    Limited Availability
    Beautiful 39ft Double Decker Carver Mariner Luxury Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    Beautiful 39ft Double Decker Carver Mariner Luxury Yacht in Chicago, Illinois

    New
    $350/hour
    Sea Ray 370 Sundancer Motor Yacht Rental in Chicago - USCG Captain Required
    Events in Chicago · 12 guests

    Sea Ray 370 Sundancer Motor Yacht Rental in Chicago - USCG Captain Required

    5.0
    $325/hour
    Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht
    Events in Chicago · 10 guests

    Chicago Lakefront Cruise on 33ft Ciera Bayliner Yacht

    5.0
    $150/hour
    Lakeside Paradise Escape with Premier 310 Escalante Double Decker Tritoon
    Powerboats in Dandridge · 12 guests

    Lakeside Paradise Escape with Premier 310 Escalante Double Decker Tritoon

    New
    $425/hour
    46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 13 guests

    46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois

    5.0
    $400/hour
    Limited Availability
    35’ Sea Ray Yacht, Playpen, River Cruises up to 13 people Captain included!
    Events in Chicago · 11 guests

    35’ Sea Ray Yacht, Playpen, River Cruises up to 13 people Captain included!

    5.0
    $300/hour
    Limited Availability
    Burnham Harbor Experience Chicago like never before on 35ft Maxum Motor Yacht
    Events in Chicago · 10 guests

    Burnham Harbor Experience Chicago like never before on 35ft Maxum Motor Yacht

    4.9
    $200/hour
    Limited Availability
    42ft Sea Ray Motor Yacht in Chicago, Burnham Harbor (Up to 12 guests)
    Events in Chicago · 12 guests

    42ft Sea Ray Motor Yacht in Chicago, Burnham Harbor (Up to 12 guests)

    New
    $300/hour
    Sea Ray 460 Sundancer Yacht - Enjoy the summer Chicago scene!
    Events in Chicago · 12 guests

    Sea Ray 460 Sundancer Yacht - Enjoy the summer Chicago scene!

    New
    $400/hour

    Top Destinations Nearby

    Local Tours 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. MV

      Matina

      39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included

      George was the best! Paris’ Dream was a dream day for our bride to be. Captain Dennis was also the best, a great Dj and overall good energy to be around.

    4. 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!

    5. Reanna

      Reanna

      Cruisers Y3375 Express Yacht Downtown Chicago Experience

      The boat day was our favorite part of our bachelorette trip. We had the best time and we loved Captain Sam! 10/10 recommend this company!

    6. KD

      Kareem

      2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

      Nilufar made the booking process so easy and we had no issues from start to finish!

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