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    Illinois, US Boat Rentals & Yacht Charters

    4.9
    (5,749 Reviews)

    Page 10 of 13 • 296 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    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
    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
    62' Azimut Italian Luxury Yacht for Rent in Chicago, Illinois for 13 Guests
    Events in Chicago · 13 guests

    62' Azimut Italian Luxury Yacht for Rent in Chicago, Illinois for 13 Guests

    3.0
    $1,000/hour
    25' Tritoon w/ Captain for Rent St. Charles, MO
    Powerboats in St. Louis · 11 guests

    25' Tritoon w/ Captain for Rent St. Charles, MO

    New
    $110/hour
    High Demand
    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
    Events in Chicago · 12 guests

    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

    5.0
    $225/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
    Italian Luxury Azimut 63ft Yacht Charter for 12 Guests in Chicago
    Events in Chicago · 12 guests

    Italian Luxury Azimut 63ft Yacht Charter for 12 Guests in Chicago

    New
    $800/hour
    38ft Lagoon Catamaran Sailing Lessons in Chicago
    Tours in Chicago · 6 guests

    38ft Lagoon Catamaran Sailing Lessons in Chicago

    New
    $350+/hour
    Cest la vie!! Sea Ray 46' boat for the summertime
    Events in Chicago · 12 guests

    Cest la vie!! Sea Ray 46' boat for the summertime

    New
    $400/hour
    41' Luxury Four Winns Vista Yacht Charter in Chicago | Playpen & Skyline Cruises
    Events in Chicago · 12 guests

    41' Luxury Four Winns Vista Yacht Charter in Chicago | Playpen & Skyline Cruises

    New
    $300/hour
    27' Four Winns 225 Sundowner - Lake Michigan Charter Boat Rental with Captain
    Powerboats in Chicago · 12 guests

    27' Four Winns 225 Sundowner - Lake Michigan Charter Boat Rental with Captain

    New
    $250/hour
    eFoil Sessions in Chicagoland!
    Adventures in Gary · 6 guests

    eFoil Sessions in Chicagoland!

    New
    $250/hour
    Premium 55' Sea Ray Yacht Charter - Seakeeper Stability, Chicago Lake Michigan
    Events in Chicago · 12 guests

    Premium 55' Sea Ray Yacht Charter - Seakeeper Stability, Chicago Lake Michigan

    New
    $1,404/hour
    36ft Luxury Silverton Motor Yacht in Chicago - 12 Guests Can Relax and Have Fun
    Events in Chicago · 12 guests

    36ft Luxury Silverton Motor Yacht in Chicago - 12 Guests Can Relax and Have Fun

    New
    $275/hour
    Limited Availability
    46ft Luxury Sea Ray 410 Express Cruiser Yacht Chicago for 13 Guests
    Events in Chicago · 13 guests

    46ft Luxury Sea Ray 410 Express Cruiser Yacht Chicago for 13 Guests

    New
    $250/hour
    Instant Book
    Limited Availability
    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests
    Events in Chicago · 12 guests

    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests

    New
    Superowner
    Best of 2026
    $160+/hour
    Instant Book
    See the Gorgeous Chicago Skyline & Experience Lake Michigan on 33' Sea Ray Yacht
    Events in Chicago · 12 guests

    See the Gorgeous Chicago Skyline & Experience Lake Michigan on 33' Sea Ray Yacht

    New
    $275/hour
    Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests
    Events in Chicago · 10 guests

    Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests

    New
    $200/hour
    Chicago Luxury 32ft Chris-Craft Yacht | 12 Guests | Playpen and River Cruises
    Events in Chicago · 12 guests

    Chicago Luxury 32ft Chris-Craft Yacht | 12 Guests | Playpen and River Cruises

    New
    $250/hour
    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
    40ft Sea Ray Sundancer 370 Yacht Chicago Lights Music Fun!
    Events in Chicago · 12 guests

    40ft Sea Ray Sundancer 370 Yacht Chicago Lights Music Fun!

    New
    Superowner
    $250/hour
    High Demand
    Beautiful Sea Ray 390 Express Cruiser Yacht for 12 Guests in Chicago
    Events in Chicago · 12 guests

    Beautiful Sea Ray 390 Express Cruiser Yacht for 12 Guests in Chicago

    New
    $250/hour

    Top Destinations Nearby

    Illinois 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. AS

      Alexander

      Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

      Jason was awesome communicative and delivered amazing hospitality. Boat is huge and Luxurious. Can’t wait to do it again

    5. SD

      Shreerupa

      44ft Regal Commodore Motor Yacht Charter In Chicago

      Robert was fantastic. He was very prompt with his communication. The boat was very clean and had plenty of seats and space to accommodate our group of 13. Our primary goal was watching the Air & Water show which was running late. Robert was kind enough to give us extra time for free so that we had the best experience and did not miss the main attraction of the show.

    6. FM

      Fernando

      44ft Regal Commodore Motor Yacht Charter In Chicago

      Captain Robert gave us an unforgettable day on the water! From the moment we boarded, he made everyone feel welcome and comfortable. His professionalism, local knowledge, and easygoing personality created the perfect balance of safety and fun. The boat was spotless, the ride was smooth, and every detail was taken care of so we could just relax and enjoy. We can’t wait to book with him again — highly recommend!

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