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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,744 Reviews)

    Page 7 of 12 • 287 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Luxury 35ft Larson Cabrio Yacht | Chicago Lakefront Experience
    Events in Chicago · 10 guests

    Luxury 35ft Larson Cabrio Yacht | Chicago Lakefront Experience

    New
    $300/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
    Charter on Lake Michigan and the Chicago River | Sea Ray 300 Sundancer Yacht
    Powerboats in Chicago · 12 guests

    Charter on Lake Michigan and the Chicago River | Sea Ray 300 Sundancer Yacht

    New
    $220+/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
    Explore Chicago's Skyline and Waters on 34' Sea Ray 'Succession' Private Yacht
    Events in Chicago · 12 guests

    Explore Chicago's Skyline and Waters on 34' Sea Ray 'Succession' Private Yacht

    5.0
    $315/hour
    Limited Availability
    50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package
    Powerboats in Chicago · 36 guests

    50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package

    4.5
    $1,350/hour
    Limited Availability
    Sleek 51' Luxury Motor Yacht | Parties and Events in Chicago - Fuel Included
    Events in Chicago · 12 guests

    Sleek 51' Luxury Motor Yacht | Parties and Events in Chicago - Fuel Included

    New
    Superowner
    Best of 2026
    $240/hour
    See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht
    Events in Chicago · 13 guests

    See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht

    5.0
    Superowner
    Best of 2026
    $300/hour
    Limited Availability
    Gorgeous 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing in Chicago
    Events in Chicago · 12 guests

    Gorgeous 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing in Chicago

    5.0
    $600/hour
    Limited Availability
    "Excelling in Excellence" 46' Azimut Yacht Charter in Chicago, IL
    Events in Chicago · 13 guests

    "Excelling in Excellence" 46' Azimut Yacht Charter in Chicago, IL

    New
    $772/hour
    20' Lund Bass Boat for 3 in Chicago, Illinois
    Fishing in Chicago · 3 guests

    20' Lund Bass Boat for 3 in Chicago, Illinois

    5.0
    $67/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
    Limited Availability
    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago
    Events in Chicago · 13 guests

    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago

    4.9
    $400/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
    50' Multi-level Sea Ray Luxury Yacht with Party up to 12 in Chicago
    Events in Chicago · 12 guests

    50' Multi-level Sea Ray Luxury Yacht with Party up to 12 in Chicago

    5.0
    Superowner
    Best of 2026
    $350/hour
    Limited Availability
    40' Regal Commandore Luxury Cruiser in Chicago
    Events in Chicago · 12 guests

    40' Regal Commandore Luxury Cruiser in Chicago

    5.0
    $300/hour
    Spectacular 55ft Sea Ray 520 Fly Motor Yacht In Chicago
    Events in Chicago · 13 guests

    Spectacular 55ft Sea Ray 520 Fly Motor Yacht In Chicago

    New
    $700/hour
    Limited Availability
    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
    Sailing in Chicago · 12 guests

    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

    4.8
    $245/hour
    Instant Book
    Limited Availability
    Sailing Lessons with Chicago's #1 Rated Sailing School
    Tours in Chicago · 6 guests

    Sailing Lessons with Chicago's #1 Rated Sailing School

    5.0
    $175+/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
    Limited Availability
    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
    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
    Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
    Events in Chicago · 13 guests

    Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

    4.9
    Superowner
    Best of 2026
    $235/hour

    Top Destinations Nearby

    Chicago Reviews

    1. Eric

      Eric

      Sailing Lessons with Chicago's #1 Rated Sailing School

      I had a four hour private lesson with Doug and small crew. All were very helpful and knowledgeable, it was a great learning experience. I look forward to joining them again.

    2. RK

      Rish

      Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

      I proposed to my girlfriend on the Sea Ray boat, and it was an unforgettable experience. Kevin was fantastic to work with—he coordinated everything seamlessly and responded very quickly to all my questions. Captain Evan was also great. They both went above and beyond to make the proposal and our evening truly special and memorable.

    3. SJ

      Sam

      See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht

      Kevin was professional, friendly, and - most importantly - fun. He and captain William were pro navigators and never did anything risky. They're solid guys with a great boat and I wouldn't hesitate to rent from these guys again.

    4. OH

      Olivia

      See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht

      Captain Ben and Manny were great! I would 100% book again.

    5. MS

      Mason

      Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

      Great experience all around. Our captain Alex was awesome, too.

    6. AO

      Andrea

      Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago

      Excellent. Booking again as we speak!

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