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    Illinois, US Boat Rentals & Yacht Charters

    4.9
    (5,828 Reviews)

    Page 7 of 13 • 298 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Limited Availability
    Chicago 40ft Formula Performance Cruiser for Up to 13 Guests
    Events in Chicago · 13 guests

    Chicago 40ft Formula Performance Cruiser for Up to 13 Guests

    5.0
    $349/hour
    High Demand
    72ft Chris Craft Motor Yacht Chicago for 49 Guest Events
    Events in Chicago · 49 guests

    72ft Chris Craft Motor Yacht Chicago for 49 Guest Events

    5.0
    Superowner
    $1,350/hour
    Premium Sea-Doo Jet Ski Rental – Explore Chicago from the Water
    Water Sports in Chicago · 2 guests

    Premium Sea-Doo Jet Ski Rental – Explore Chicago from the Water

    New
    $150/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
    Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat
    Powerboats in Chicago · 12 guests

    Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat

    New
    $325/hour
    Limited Availability
    Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer
    Powerboats in Chicago · 6 guests

    Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

    5.0
    $235+/hour
    Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago
    Events in Chicago · 12 guests

    Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago

    5.0
    $325/hour
    Tiki Themed 24' Key West Boat with Captain & Beverage Package | Chicago
    Powerboats in Chicago · 6 guests

    Tiki Themed 24' Key West Boat with Captain & Beverage Package | Chicago

    5.0
    $200/hour
    34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!
    Events in Chicago · 12 guests

    34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!

    New
    $300/hour
    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
    Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
    Events in Chicago · 12 guests

    Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience

    5.0
    $350/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
    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 Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht
    Powerboats in Chicago · 12 guests

    Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht

    4.9
    Superowner
    $300/hour
    Fun 27' Chaparral Sunesta Boat Rental in Chicago: Skyline Views on Lake Michigan
    Powerboats in Chicago · 8 guests

    Fun 27' Chaparral Sunesta Boat Rental in Chicago: Skyline Views on Lake Michigan

    5.0
    $284/hour
    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
    50ft Sea Ray 440 Express Bridge Double Deck Yacht in Chicago!
    Events in Chicago · 13 guests

    50ft Sea Ray 440 Express Bridge Double Deck Yacht in Chicago!

    New
    Superowner
    Best of 2026
    $300/hour
    Limited Availability
    Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper
    Events in Chicago · 12 guests

    Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper

    4.7
    $250+/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
    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
    1962 Chris Craft Yacht Charter on the Chicago River!
    Events in Chicago · 6 guests

    1962 Chris Craft Yacht Charter on the Chicago River!

    5.0
    $250+/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
    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

    Top Destinations Nearby

    Illinois Reviews

    1. BD

      Brittany

      Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

      We had a great time on our trip with Diego! He had a great route planned for us to see the river and stop by the playpen and see the city from the lake. He was a great communicator before the trip. He let us know all the details we needed ahead of time to have a smooth trip. We all had a wonderful time!! Highly recommend!!

    2. SG

      Sara

      72ft Chris Craft Motor Yacht Chicago for 49 Guest Events

      Amazing experience! We hosted clients for an appreciation event on the lake and it was amazing. Captain Rich and crew were so wonderful to work with and ensured we had a great time.

    3. JB

      Janell

      Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

      It was great time with Diego, showed us various sites and attractions throughout the Chicago area. Definitely would book with him again.

    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. TM

      Tamila

      Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

      Extremely professional. On time, easy and fast communication. Very accommodating. Overall an awesome experience.

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