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    Lake Michigan, US Boat Rentals & Yacht Charters

    4.9
    (6,278 Reviews)

    Page 9 of 16 • 361 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev
    Events in Chicago · 13 guests

    Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

    5.0
    Superowner
    Best of 2026
    $500/hour
    Skipperliner Tiki Party Yacht for 50–90 Guests All Inclusive in Chicago
    Events in Chicago · 90 guests

    Skipperliner Tiki Party Yacht for 50–90 Guests All Inclusive in Chicago

    5.0
    $1,500/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
    Luxury 45’ Catamaran in Chicago | Up to 40 Guests
    Events in Chicago · 40 guests

    Luxury 45’ Catamaran in Chicago | Up to 40 Guests

    New
    Superowner
    Best of 2026
    $900/hour
    Instant Book
    24' Pontoon Rental deliver to your dock /servicing Lakes South West Michigan
    Powerboats in Holland · 13 guests

    24' Pontoon Rental deliver to your dock /servicing Lakes South West Michigan

    5.0
    $268+/day
    40ft Chris Craft for Fishing or Cruising on Lake Michigan
    Fishing in Racine · 6 guests

    40ft Chris Craft for Fishing or Cruising on Lake Michigan

    5.0
    $145/hour
    2020 Sea Ray SLX 400 Motor Yacht in Chicago, Illinois for 12 Guests
    Events in Chicago · 12 guests

    2020 Sea Ray SLX 400 Motor Yacht in Chicago, Illinois for 12 Guests

    5.0
    $1,000/hour
    Limited Availability
    Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties
    Events in Chicago · 12 guests

    Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

    5.0
    Superowner
    Best of 2026
    $400/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
    Gorgeous 26ft Chaparral 257SSX Bowrider in Chicago
    Powerboats in Chicago · 9 guests

    Gorgeous 26ft Chaparral 257SSX Bowrider in Chicago

    5.0
    $150/hour
    High Demand
    68' Luxurious Chris Craft Roamer Yacht Private Yacht Charters in Chicago
    Events in Chicago · 45 guests

    68' Luxurious Chris Craft Roamer Yacht Private Yacht Charters in Chicago

    5.0
    $1,750/hour
    Limited Availability
    New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain
    Powerboats in Chicago · 13 guests

    New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain

    5.0
    Superowner
    $275/hour
    Limited Availability
    16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!
    Powerboats in Chicago · 16 guests

    16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!

    New
    Superowner
    Best of 2026
    $650/hour
    Limited Availability
    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!
    Events in Chicago · 12 guests

    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

    5.0
    Superowner
    Best of 2026
    $220/hour
    Instant Book
    Limited Availability
    Stunning 51' Sea Ray Sundancer with USCG Captain in Chicago
    Events in Chicago · 12 guests

    Stunning 51' Sea Ray Sundancer with USCG Captain in Chicago

    New
    Superowner
    Best of 2026
    $450/hour
    Limited Availability
    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
    Events in Chicago · 13 guests

    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

    5.0
    $225/hour
    Limited Availability
    37ft Cruiser Express Motor Yacht Charter Chicago Plus Jet Ski Included
    Events in Chicago · 12 guests

    37ft Cruiser Express Motor Yacht Charter Chicago Plus Jet Ski Included

    5.0
    $350/hour
    Limited Availability
    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
    40' Carver Motor Yacht with space all around available in Chicago
    Events in Chicago · 12 guests

    40' Carver Motor Yacht with space all around available in Chicago

    5.0
    $375/hour
    40' Regal Commandore Luxury Cruiser in Chicago
    Events in Chicago · 12 guests

    40' Regal Commandore Luxury Cruiser in Chicago

    5.0
    $300/hour
    Limited Availability
    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
    Limited Availability
    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

    Top Destinations Nearby

    Lake Michigan 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. JN

      Jessica

      Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

      Such a lovely trip. Up to the trip Kevin and his team were extremely responsive. This was amazing and we will be doing this again! Thanks!

    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. VF

      Victoria

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

      Super great! He was so responsive and had a blast at the Playpen!

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