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Find Yacht Rentals and Charters Near You

4.9
(29,054 Reviews)

Page 9 of 10 • 240 listings

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Events in Chicago · 13 guests

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

5.0
$200/hour
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
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. SG

    Samantha

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

    This was the most fun I’ve had in Chicago so far, the weather was beautiful and we had a smooth ride. We rented the boat for a bachelorette and communicating with Kevin was so easy, he was able to answer all of our questions patiently, he was so kind and made the whole process so easy. Our captain was Riley, I would totally recommend him, he was puntual, funny and made our trip so fun and also made us feel so comfortable and safe. He was clear with instructions and was patient with us as well. I would totally recommend Kevin and his boat to everyone!

  4. JE

    John

    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

    My group had a fantastic time aboard Jason's boat with our captain, Jimmy. Jason was in regular communication with me leading up to the excursion so we felt prepared. The boat is just as described and comfortably fit our group for a day out on the water. Would definitely book again!

  5. AE

    Ahmad

    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

    This is our third time renting a boat from Jason, and once again, we were completely impressed. The entire experience, from the boat itself to the communication, is always top-notch. For this outing, we had Jimmy as our captain, and I cannot recommend him enough! He was fantastic and truly elevated the whole experience for our group. It is always a pleasure dealing with Jason, and we already can't wait to rent from him again!

  6. 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!