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Rent a Boat or Yacht in Chicago, Illinois

Page 2 of 10239 listings

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
$220/hour
Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois
Events in Chicago · 13 guests

Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois

5.0
$400/hour
**Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**
Events in Chicago · 12 guests

**Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**

5.0
$300/hour
Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL
Events in Chicago · 13 guests

Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL

4.9
$275/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
Best of 2025
$200/hour
Li'l Red, Crownline CR250 Cabin Cruiser
Powerboats in Chicago · 10 guests

Li'l Red, Crownline CR250 Cabin Cruiser

5.0
Best of 2025
$325/hour
Instant Book
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
$225/hour
Sea Ray Express 390 Luxury Charter in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0
$250/hour
14 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 14 guests

14 Passenger Captained Party & Event Boat in Chicago, Illinois!

5.0
Superowner
$600/hour
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
$300/hour
Instant Book
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
Events in Chicago · 12 guests

Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!

5.0
$250/hour
Instant Book
Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
Events in Chicago · 10 guests

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

4.9
Best of 2025
$275+/hour
Instant Book
27' Chris Craft with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

4.9
Superowner
$240/hour
Instant Book
36ft Carver Mariner Motor Yacht in Chicago
Events in Chicago · 12 guests

36ft Carver Mariner Motor Yacht in Chicago

4.8
$300/hour
Maxum Yacht 44' in Chicago
Powerboats in Chicago · 13 guests

Maxum Yacht 44' in Chicago

4.9
Superowner
Best of 2025
$268/hour
Stylish elegance and spacious comfort ... your best time ever!
Events in Chicago · 12 guests

Stylish elegance and spacious comfort ... your best time ever!

4.9
$250/hour
Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
Powerboats in Chicago · 12 guests

Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht

4.9
Superowner
Best of 2025
$300/hour
*** $200 to $225 hr***Weekend Charter Rental - 33' Maxum!
Events in Chicago · 8 guests

*** $200 to $225 hr***Weekend Charter Rental - 33' Maxum!

4.9
$175/hour
70' EXCLUSIVE Motor Yacht NEW to Chicago
Events in Chicago · 13 guests

70' EXCLUSIVE Motor Yacht NEW to Chicago

4.8
Superowner
$999/hour
Downtown Chicago, Party on the Lake!
Powerboats in Chicago · 10 guests

Downtown Chicago, Party on the Lake!

4.9
Best of 2025
$270/hour
25ft Rinker - Captained included in price- Chicago
Powerboats in Chicago · 7 guests

25ft Rinker - Captained included in price- Chicago

4.9
Superowner
$199/hour
Instant Book
46' Spacious Portofino Party Yacht in Chicago For Every Occasion
Events in Chicago · 12 guests

46' Spacious Portofino Party Yacht in Chicago For Every Occasion

4.5
$250/hour
Instant Book
38-ft Party Pontoon for Up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

38-ft Party Pontoon for Up to 20 Guests in Chicago

5.0
Superowner
Best of 2025
$680/hour
50' Multi-level Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

50' Multi-level Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2025
$350/hour

Chicago Reviews

  1. BM

    Bridget

    38-ft Party Pontoon for Up to 20 Guests in Chicago

    We had an incredible experience. We booked for a co-ed bachelorette party. The captain and other staff on board were SO friendly and accommodating. The cooler was plenty big, the bathroom was clean, and we had a nice space to set up our sandwiches. Great experience!

  2. Federica

    Federica

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I was so happy to do this experience but I didn’t know that I was going to like it so much ! I would recommend having this boat for a 2 date or double date ! The owners are really lovely but the best part is going to the pope and sitting there ! Make sure you bring wine, glassware and whatever you want to have ! 2 hours was a perfect time for us! Us we were lucky enough to have of the best sunsets of the season !

  3. vp

    vadim

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I want to thank Nijole for her work . Everything was perfectly organized, swimming and sailing. My daughter got seasick and we received full support from the captain. There was also a miracle dog on board ! Dog swam with us and gave us a good mood! Thank you very much! If you want to have a wonderful time sailing, then you are definitely to Nijole! With respect, Vadim Pliss!

  4. AL

    Adam

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    We loved our experience with Nijole. They took us all around the lake and we loved every minute of it. We even got to swim! They are also a very fun time to hang out with and enjoy the day. Definitely recommend and we will be booking with them multiple times this boating season.

  5. Rachel

    Rachel

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    Nijole was incredibly helpful, communicative, and kind. She was responsive and went above and beyond to help us reschedule when bad weather struck. We had a lovely trip and she and her husband were delightful to be around! I highly recommend their boat and I can’t wait to sail with them again sometime.

  6. SS

    Sam

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I can’t begin to express how kind and courteous our hosts were. They made our trip incredible from the time we stepped on the boat until the time we departed. My friends and I all felt that they went above and beyond to make our experience memorable. If you are looking for a good time on the water look no further and book right here!