We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

Rent a Boat or Yacht in Chicago, Illinois

Page 2 of 11262 listings

42ft Searay Sundancer | Big Boat Small Price END OF SUMMER SALE!
Events in Chicago · 10 guests

42ft Searay Sundancer | Big Boat Small Price END OF SUMMER SALE!

5.0
$200/hour
39' Sea Ray for Rent in Chicago, Illinois!
Events in Chicago · 12 guests

39' Sea Ray for Rent in Chicago, Illinois!

5.0
$350+/hour
Captain Memo's 28 ft. Sea Ray in Chicago
Events in Chicago · 6 guests

Captain Memo's 28 ft. Sea Ray in Chicago

5.0
Superowner
$290/hour
36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Events in Chicago · 6 guests

36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

4.9
Best of 2023
$280/hour
NEW!!! 35' Luxury Motor Yacht with 4’ swim platform. Get 10% off for Weekend
Events in Chicago · 12 guests

NEW!!! 35' Luxury Motor Yacht with 4’ swim platform. Get 10% off for Weekend

4.7
$180+/hour
LABOR DAY WEEKEND DEAL $250/HOUR & UP ON 40' CRUISER OR 33' BAYLINER
Events in Chicago · 12 guests

LABOR DAY WEEKEND DEAL $250/HOUR & UP ON 40' CRUISER OR 33' BAYLINER

4.8
$250+/hour
Last Minute Playpen Clean Beautiful Boat LOA 40' Sundancer
Events in Chicago · 13 guests

Last Minute Playpen Clean Beautiful Boat LOA 40' Sundancer

5.0
$250/hour
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
Best of 2023
$220/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
Best of 2023
$250/hour
Chicago Summer Vibes - Soak up the Sun in Style!
Powerboats in Chicago · 6 guests

Chicago Summer Vibes - Soak up the Sun in Style!

5.0
$300/hour
Experience Lake Michigan like never before on Beautiful 35ft Maxum
Events in Chicago · 10 guests

Experience Lake Michigan like never before on Beautiful 35ft Maxum

5.0
$225/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
42FT Regal Commodore Express Cruiser
Events in Chicago · 13 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2023
$245/hour
44' Sea Ray Express Luxury Motor Yacht Rental in Chicago
Events in Chicago · 12 guests

44' Sea Ray Express Luxury Motor Yacht Rental in Chicago

4.9
Superowner
$299/hour
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$200/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
Charter a 39' Luxury SeaRay Sundancer 390 for 11 guests w/ Captain in Chicago
Events in Chicago · 11 guests

Charter a 39' Luxury SeaRay Sundancer 390 for 11 guests w/ Captain in Chicago

5.0
$350/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
44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!
Events in Chicago · 12 guests

44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!

5.0
$275+/hour
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
Searay  Sundancer Cruiser 36' LOA $250 an hour
Events in Chicago · 13 guests

Searay Sundancer Cruiser 36' LOA $250 an hour

5.0
$250/hour
Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois
Powerboats in Chicago · 8 guests

Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois

5.0
$225/hour
52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!
Events in Chicago · 12 guests

52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!

5.0
$300/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
Best of 2023
$400/hour

Chicago Reviews

  1. RG

    Ravi

    Captain Memo's 28 ft. Sea Ray in Chicago

    An awesome experience - right from booking the trip, the trip itself, and the warmth and responsiveness of Capt Memo. The boat was awesome - clean and with space up front and in the back of the boat. Capt Memo asked us upfront how we wanted to spend our time and ensured we got exactly what we wanted. He also took some great pictures which he shared promptly. And he engaged with us when we welcomed it but also gave us space when we wanted it. All in all, we loved the experience and will certainly be back

  2. FN

    Francis

    70' EXCLUSIVE Motor Yacht NEW to Chicago

    Damian and Monica (and Jimmy) were a pleasure as captain, staff, and assisting with our trip. Everything was on time and their initial instructions were easy to understand and friendly. Our trip included both the the river and lake and was a beautiful day. Our originally scheduled Saturday had bad weather forecasted and we were lucky enough to reschedule for the day after. This was a surprise for my Mom and when the boat arrived it was huge, clean and ready to go. We brought our own food, drinks, and also had the ability to play our own music. The boat was the biggest on the water and we loved the multiple locations on the boat to hang out to eat and drink. It was an unforgettable day and I would not hesitate to use them again. I highly recommend it!

  3. mm

    maira

    Captain Memo's 28 ft. Sea Ray in Chicago

    An overall wonderful experience! Communication was great with the captain from the start as he guided us through the phone to find the boat, the boat itself was clean with excellent service from the Bluetooth speaker to the cooler with ice; It was a Saturday night so witnessing the fireworks on the water is definitely a 10/10, my toddler very much enjoyed it as well! Thank you captain Memo 😊

  4. TH

    Tory

    Captain Memo's 28 ft. Sea Ray in Chicago

    Memo was a great captain! We appreciated his communication immediately upon booking all the way through our reservation. Throughout our trip, he made sure the experience was exactly what we wanted. Would definitely recommend him to anyone looking for the ideal Chicago boating experience.

  5. KC

    Kaylee

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

    We had the absolute BEST time with Captain Kevin, Captain Steve, and Skipper Manny for my bachelorette party! Even despite the choppy water, they made sure to keep us safe AND have a great time. I wish I could give them 6 stars. 10/10 recommend!!

  6. IW

    Ian

    Captain Memo's 28 ft. Sea Ray in Chicago

    One of the best captains I’ve had. I’ve used Get My Boat in Miami numerous times but Memo really blew it out of the water. So nice, took plenty of pictures for us and had some great recommendations