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Find Yacht Rentals and Charters Near You

4.8
(29,015 Reviews)

Page 9 of 10 • 240 listings

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests
Events in Chicago · 12 guests

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

3.9
$250/hour
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
52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!
Events in Chicago · 13 guests

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

5.0
$225+/hour
New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain
Powerboats in Chicago · 13 guests

New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain

4.6
Superowner
$275/hour
50ft Searay 400 Motor Yacht - Lake Michigan Chicago - Up to 13 Guests
Events in Chicago · 13 guests

50ft Searay 400 Motor Yacht - Lake Michigan Chicago - Up to 13 Guests

5.0
$300/hour
Scenic Lake Michigan Cruises on a 35’ Formula Sun Sport Yacht - 12 Guests
Events in Chicago · 12 guests

Scenic Lake Michigan Cruises on a 35’ Formula Sun Sport Yacht - 12 Guests

5.0
$350/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

1.5
$300/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
$350/hour
Class up the Playpen and Chicago River | Vintage Sea Ray 300 Sundancer Yacht
Powerboats in Chicago · 10 guests

Class up the Playpen and Chicago River | Vintage Sea Ray 300 Sundancer Yacht

New
$140/hour
Luxury 42' Sea Ray Motor Yatch | Chicago River and Lake Experience
Events in Chicago · 12 guests

Luxury 42' Sea Ray Motor Yatch | Chicago River and Lake Experience

New
$450/hour
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
See Chicago like no one else can! Rent Sea Ray 350 Sundancer Motor Yacht!
Events in Chicago · 12 guests

See Chicago like no one else can! Rent Sea Ray 350 Sundancer Motor Yacht!

New
$300+/hour
Diversey Harbor: Gorgeous 46' Sea Ray Luxury Yacht for 13 Guests
Events in Chicago · 13 guests

Diversey Harbor: Gorgeous 46' Sea Ray Luxury Yacht for 13 Guests

5.0
Superowner
Best of 2026
$225/hour
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
Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
Events in Chicago · 12 guests

Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

4.9
Superowner
Best of 2026
$160+/hour
Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!
Events in Chicago · 12 guests

Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!

4.9
Superowner
Best of 2026
$400/hour
Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties
Events in Chicago · 12 guests

Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties

5.0
Superowner
Best of 2026
$400/hour
37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen
Events in Chicago · 12 guests

37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen

5.0
Superowner
Best of 2026
$220/hour
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

5.0
Superowner
Best of 2026
$160+/hour
Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!
Events in Chicago · 12 guests

Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!

5.0
Superowner
Best of 2026
$220/hour
Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations
Powerboats in Chicago · 12 guests

Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

5.0
Superowner
Best of 2026
$190/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
Stunning 51' Sea Ray Sundancer with USCG Captain in Chicago
Events in Chicago · 12 guests

Stunning 51' Sea Ray Sundancer with USCG Captain in Chicago

New
Superowner
Best of 2026
$450/hour
Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht
Events in Chicago · 12 guests

Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht

5.0
Superowner
Best of 2026
$325/hour

Local Motor Yacht Reviews

  1. MD

    Michelle

    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

    10/10 experience! Nasco’s team went above and beyond to accommodate us when the weather was looking iffy. We had an amazing time and the boat was even better than the pictures. Highly recommend!

  2. MF

    Matthew

    Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

    Nasco was very prompt and clear in his communication and graciously answered my many questions. The boat was great and Captain Mike G. was awesome. Our group of 12 had a great time and we would definitely book again!

  3. Devon

    Devon

    Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

    Arthur and his crew were great at accommodating us for an event at the playpen on one of the busiest days of the summer. Arthur was very responsive leading up to the day and even helped find another captain after ours cancelled. Communication the day of wasn’t the best as I believe there was another charter before us but we were able to finally link up and take off for the full allotted time. We had a blast!

  4. Ashwin

    Ashwin

    52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

    We had an incredible experience with Jason, and his captain! We were chartering for a proposal and they were kind enough to upgrade us. The boat was beautiful, spacious, and made the day feel so special. Our captain was beyond amazing, fun, and knew exactly where to go for the perfect skyline backdrop. Everything was organized seamlessly from start to finish, with clear directions and details that made the whole process stress-free. I would absolutely use them again and highly recommend them to anyone looking for a first-class experience on the lake!

  5. Beatris

    Beatris

    52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

    My experience booking with Jason was a 10/10 through and through from beginning to end. The entire process was seamless, from booking the boat rental to the actual boat day. Jason provided great communication and answered all of my questions promptly. The boat itself was even better than I imagined, very beautiful with a lot of space, very clean and well kept. The captain that was recommended was a great time and really took care of us. I thoroughly enjoyed my entire experience and will be booking with him again!

  6. Jahkayah

    Jahkayah

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

    What a fantastic experience! I rented Alex's boat yesterday and had an absolute blast with my group of 12 friends. From the moment we arrived, Alex was super friendly and welcoming. He showed us around the boat and made sure we felt comfortable and at ease. The boat itself was immaculate - clean, well-maintained, and organized to perfection. Alex had thought of everything to ensure our day on the water was stress-free and enjoyable. His assistant was also super helpful in getting us settled and answering any questions we had. Alex himself was an absolute pleasure to be around. He was knowledgeable about the area and gave us great recommendations for things to do and see. His enthusiasm was infectious, and he really made us feel like we were part of his own little crew. We had an amazing time cruising around the water, taking in the sights, and enjoying each other's company. The boat handled beautifully, and we were able to fit all 12 of us comfortably. Overall, I would highly recommend renting from Alex. His attention to detail, warm hospitality, and love for boating make for a truly unforgettable experience. We can't wait to come back and do it again!