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    4.9
    (28,377 Reviews)

    Page 8 of 10 • 240 listings

    Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises
    Events in Chicago · 13 guests

    Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises

    5.0
    $750/hour
    High Demand
    Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible SoundSystem!
    Events in Chicago · 12 guests

    Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible SoundSystem!

    5.0
    $350/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
    2018 Luxury 52ft Azimut Fly 50 Motor Yacht Rental in Chicago, IL for 13 Guests
    Events in Chicago · 13 guests

    2018 Luxury 52ft Azimut Fly 50 Motor Yacht Rental in Chicago, IL for 13 Guests

    5.0
    $1,000/hour
    Limited Availability
    The Newest Boat in the Fleet: 40' Luxury Chris Craft for Charter in Chicago
    Events in Chicago · 12 guests

    The Newest Boat in the Fleet: 40' Luxury Chris Craft for Charter in Chicago

    New
    $300/hour
    Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran
    Sailing in Chicago · 13 guests

    Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

    5.0
    $440/hour
    Limited Availability
    Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
    Events in Chicago · 8 guests

    Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

    5.0
    $180/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
    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
    No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor
    Events in Chicago · 13 guests

    No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor

    New
    $250/hour
    Instant Book
    Limited Availability
    Captained Charter on 45’ Custom Built Double Decker Power Catamaran - 44 Guests
    Powerboats in Chicago · 44 guests

    Captained Charter on 45’ Custom Built Double Decker Power Catamaran - 44 Guests

    5.0
    $1,100/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
    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
    Events in Chicago · 8 guests

    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

    5.0
    $500/hour
    Limited Availability
    Catch a summer vibe on the water aboard 39' Sea Ray motor yacht
    Events in Chicago · 12 guests

    Catch a summer vibe on the water aboard 39' Sea Ray motor yacht

    New
    $225/hour
    Limited Availability
    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
    High Demand
    Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!
    Events in Chicago · 120 guests

    Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!

    5.0
    $1,500/hour
    Limited Availability
    Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois
    Powerboats in Chicago · 8 guests

    Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

    4.6
    $275/hour
    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina
    Events in Chicago · 13 guests

    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

    5.0
    $300/hour
    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
    High Demand
    Chicago Boat Cruise on Captained Sea Ray Sundancer 260 Motor Yacht
    Events in Chicago · 8 guests

    Chicago Boat Cruise on Captained Sea Ray Sundancer 260 Motor Yacht

    5.0
    $275/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
    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
    Chicago's 43' Tiara Luxury Getaway on Lake Michigan for Groups & Family
    Events in Chicago · 12 guests

    Chicago's 43' Tiara Luxury Getaway on Lake Michigan for Groups & Family

    New
    $605/hour
    Limited Availability
    49 Passengers 57' Power Catamaran - Perfect For Events in Chicago
    Events in Chicago · 49 guests

    49 Passengers 57' Power Catamaran - Perfect For Events in Chicago

    5.0
    Superowner
    $1,000/hour

    Top Destinations Nearby

    Local Motor Yacht Reviews

    1. YL

      Yiming

      Captained Charter on 45’ Custom Built Double Decker Power Catamaran - 44 Guests

      The captain and crew were professional, attentive, and incredibly welcoming. They took the time to make all 35 of our guests feel comfortable and safe. The boat was well-maintained, spacious, and perfect for a large group. The night was flawless. I highly recommend booking a private boat tour if you want a memorable, stress-free group outing. We couldn't have asked for a better day on the water!

    2. IS

      Isabella

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

      I booked Kevin's boat for my bachelorette and had an amazing experience. The boat was beautiful, clean, and had plenty of room for 9 girls to spread out and tan! The staff was great and I would definitely recommend it!

    3. EE

      Emily

      Captained Charter on 45’ Custom Built Double Decker Power Catamaran - 44 Guests

      Chris and his team (Phaedra and Mac) were absolutely amazing. They accommodated our 17 person bachelorette party and were SO fun and professional. We will be talking about this boat trip for years to come. 11/10 recommend knockout charters!

    4. Kristin

      Kristin

      Captained Charter on 45’ Custom Built Double Decker Power Catamaran - 44 Guests

      Incredible experience for my best friend’s bachelorette. The crew is so kind and served us drinks/food etc the entire time so we could focus on having fun! Great sound system as well! We felt very taken care of and highly recommend for an unforgettable experience!

    5. HB

      Holly

      Captained Charter on 45’ Custom Built Double Decker Power Catamaran - 44 Guests

      Such a fabulous crew! Everything went perfectly. One of the best graduation parties we have ever thrown. So happy we were able to book on this boat with this crew!

    6. 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!

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