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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,781 Reviews)

    Page 8 of 12 • 287 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Limited Availability
    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
    Limited Availability
    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
    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
    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests
    Events in Chicago · 12 guests

    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests

    New
    $300/hour
    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

    5.0
    $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
    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
    High Demand
    39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included
    Events in Chicago · 12 guests

    39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included

    5.0
    $350+/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
    Limited Availability
    53' Cruiser Yacht with Flybridge and Sundeck for 11 Guests in Chicago
    Events in Chicago · 12 guests

    53' Cruiser Yacht with Flybridge and Sundeck for 11 Guests in Chicago

    4.9
    Superowner
    $375/hour
    High Demand
    Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain
    Powerboats in Chicago · 8 guests

    Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain

    4.4
    $250/hour
    Limited Availability
    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
    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
    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
    41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago
    Events in Chicago · 12 guests

    41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago

    5.0
    Superowner
    Best of 2026
    $375+/hour
    Limited Availability
    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
    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
    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
    $400/hour
    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
    40ft Regal Luxury Motor Yacht For 12 People in Chicago (discounted weekday)
    Events in Chicago · 12 guests

    40ft Regal Luxury Motor Yacht For 12 People in Chicago (discounted weekday)

    New
    $275/hour
    Limited Availability
    27ft Sea Ray Sundancer Cruiser on Lake Michigan near Chicago for Up to 8 Guests
    Events in Chicago · 8 guests

    27ft Sea Ray Sundancer Cruiser on Lake Michigan near Chicago for Up to 8 Guests

    5.0
    $160/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
    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

    Top Destinations Nearby

    Chicago Reviews

    1. MV

      Matina

      39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included

      George was the best! Paris’ Dream was a dream day for our bride to be. Captain Dennis was also the best, a great Dj and overall good energy to be around.

    2. 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!

    3. TM

      Taylor

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

      The boat was awesome!! Marty was easy to communicate with. We had a blast and would definitely rent again

    4. AS

      Ally

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

      Amazing experience, incredibly professional, clean & kind! 10/10 would recommend!

    5. AW

      Ashley

      Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

      Very responsive and helpful. Great experience!

    6. DC

      Derek

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

      Martin and his vessel were very well kept. The list of captains provided were very professional and polite. Martin was very prompt with communication and worked with each change needed through the process of scheduling the trip. I would very much so recommend him and his services. The trip was a success and enjoyable

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