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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,793 Reviews)

    Page 8 of 12 • 288 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    51' Sea Ray Sundancer for exciting cruises on Lake Michigan
    Events in Chicago · 12 guests

    51' Sea Ray Sundancer for exciting cruises on Lake Michigan

    New
    $788/hour
    38' Chaparral Signature Motor Yacht In Chicago - 13 Guests Capacity
    Events in Chicago · 13 guests

    38' Chaparral Signature Motor Yacht In Chicago - 13 Guests Capacity

    New
    $642/hour
    Chicago Luxury Cruise on 64ft Sunseeker Motor Yacht for 12 Guests
    Events in Chicago · 12 guests

    Chicago Luxury Cruise on 64ft Sunseeker Motor Yacht for 12 Guests

    5.0
    $1,700/hour
    Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago
    Events in Chicago · 10 guests

    Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago

    5.0
    $400/hour
    Limited Availability
    Luxury Multi-Level Carver 38' Yacht with Premium Sound & Spacious Layout
    Events in Chicago · 12 guests

    Luxury Multi-Level Carver 38' Yacht with Premium Sound & Spacious Layout

    5.0
    $225/hour
    Limited Availability
    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests
    Events in Chicago · 12 guests

    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests

    4.9
    $300/hour
    High Demand
    44ft Regal Commodore Yacht Chicago Free Fuel Champagne & Island
    Events in Chicago · 13 guests

    44ft Regal Commodore Yacht Chicago Free Fuel Champagne & Island

    5.0
    $250/hour
    Limited Availability
    Luxury 35ft Sea Ray Experience in Chicago for Unforgettable Fun
    Events in Chicago · 12 guests

    Luxury 35ft Sea Ray Experience in Chicago for Unforgettable Fun

    4.7
    $350/hour
    Limited Availability
    Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations
    Powerboats in Chicago · 12 guests

    Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

    5.0
    Superowner
    Best of 2026
    $190/hour
    Instant Book
    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
    Limited Availability
    50ft Searay 400 Motor Yacht - Lake Michigan Chicago - Up to 13 Guests
    Events in Chicago · 13 guests

    50ft Searay 400 Motor Yacht - Lake Michigan Chicago - Up to 13 Guests

    New
    $300/hour
    Limited Availability
    Luxury Chaparral 277 SSX Wakeboat for 10 Guests In Chicago
    Powerboats in Chicago · 10 guests

    Luxury Chaparral 277 SSX Wakeboat for 10 Guests In Chicago

    5.0
    $175/hour
    Limited Availability
    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina
    Events in Chicago · 36 guests

    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

    5.0
    $793/hour

    Top Destinations Nearby

    Chicago 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. AO

      Alexandria

      Luxury 35ft Sea Ray Experience in Chicago for Unforgettable Fun

      I loved the experience with KG’s boat! Our charter canceled on us last minute but KG accommodated us so well. If you’re looking for a charter, book him!!

    3. 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!

    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. 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

    6. EW

      Evan

      No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

      Incredible time!! Large boat for a large group of people and so fun!!

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