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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,898 Reviews)

    Page 9 of 12 • 286 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Limited Availability
    39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
    Events in Chicago · 12 guests

    39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

    5.0
    Superowner
    Best of 2026
    $350+/hour
    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
    Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style
    Events in Chicago · 13 guests

    Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style

    5.0
    $950/hour
    Limited Availability
    Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago
    Powerboats in Chicago · 8 guests

    Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago

    New
    $248/hour
    High Demand
    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
    36’ Monterey for 12 Guests in Chicago | Playpen Party, BYOB & Captain included
    Events in Chicago · 12 guests

    36’ Monterey for 12 Guests in Chicago | Playpen Party, BYOB & Captain included

    New
    $500/hour
    Limited Availability
    Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!
    Events in Chicago · 12 guests

    Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!

    4.9
    $250/hour
    Limited Availability
    Regal 26 FasDeck for Chicago Charters, Play Pen, River Tours and Cruising
    Powerboats in Chicago · 6 guests

    Regal 26 FasDeck for Chicago Charters, Play Pen, River Tours and Cruising

    5.0
    $300/hour
    High Demand
    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!
    Events in Chicago · 13 guests

    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

    5.0
    Superowner
    $350/hour
    Limited Availability
    42' Sea Ray Sundancer Luxury Motor Yacht - Great For Outings! Diversey Harbor
    Events in Chicago · 12 guests

    42' Sea Ray Sundancer Luxury Motor Yacht - Great For Outings! Diversey Harbor

    4.0
    $150/hour
    High Demand
    New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago
    Events in Chicago · 12 guests

    New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago

    5.0
    Superowner
    $400/hour
    High Demand
    Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!
    Events in Chicago · 12 guests

    Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!

    5.0
    Superowner
    $300+/hour
    Limited Availability
    Cruise Lake Michigan Aboard 40ft Sea Ray Luxury Yacht
    Events in Chicago · 12 guests

    Cruise Lake Michigan Aboard 40ft Sea Ray Luxury Yacht

    New
    $300/hour
    High Demand
    2001 46' Sea Ray Sundancer Chartered Yacht in Chicago - 13 person capacity
    Events in Chicago · 13 guests

    2001 46' Sea Ray Sundancer Chartered Yacht in Chicago - 13 person capacity

    New
    $850/hour
    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
    Sailing in Chicago · 6 guests

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    New
    $230+/hour
    Limited Availability
    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
    Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht
    Events in Chicago · 12 guests

    Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht

    5.0
    Superowner
    Best of 2026
    $350+/hour
    Instant Book
    High Demand
    49 Passengers - Chris-Craft Private Yacht - Free Champagne Toast!
    Events in Chicago · 49 guests

    49 Passengers - Chris-Craft Private Yacht - Free Champagne Toast!

    5.0
    $1,350+/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

    5.0
    Superowner
    Best of 2026
    $950/hour
    Instant Book
    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
    Polynesian Party Boat for up to 6 people, Captain and Beverage Credit included
    Powerboats in Chicago · 6 guests

    Polynesian Party Boat for up to 6 people, Captain and Beverage Credit included

    New
    $250/hour
    Limited Availability
    Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago
    Events in Chicago · 13 guests

    Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago

    4.8
    Superowner
    $275/hour
    Limited Availability
    44’ Regal Yacht | Diversey Harbor | Free Fuel, Champagne & Two Floating Islands
    Events in Chicago · 13 guests

    44’ Regal Yacht | Diversey Harbor | Free Fuel, Champagne & Two Floating Islands

    5.0
    $300/hour
    Beautiful 37’ Sea Ray Sundancer Motor Yacht Out of Navy Pier Marina
    Events in Chicago · 6 guests

    Beautiful 37’ Sea Ray Sundancer Motor Yacht Out of Navy Pier Marina

    New
    $350+/hour

    Top Destinations Nearby

    Chicago Reviews

    1. NM

      Nancy

      Luxury 45’ Catamaran in Chicago | Up to 40 Guests

      We had such a great time on this boat. We were all surprised with how amazing it was. There was so much space we were shocked. We brought so much food and so many coolers on top of 17 people and there was still room. We all were able to sit and talk to one another. Already planning on booking this rental again. The crew was amazing and so helpful.

    2. AC

      Alexandria

      Regal 26 FasDeck for Chicago Charters, Play Pen, River Tours and Cruising

      10/10 experience. Captain was communicative the whole trip, the boat was clean and beautiful. He kept up safe and allowed us to have our fun. The respect was mutual. Thanks Captain!

    3. Olivia

      Olivia

      Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style

      Great coordination ahead of time, super convenient to board from the river, beautifully kept vintage boat!

    4. Khalia

      Khalia

      Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!

      Loved the boat had a great experience very fast response and accommodated all our needs

    5. MS

      Milap

      Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago

      Exactly as described, great operation, great captains, smooth as butter!

    6. SA

      Sonika

      'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

      Had an amazing time! Danyelle’s crew was great!

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