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Rent a Boat or Yacht in Chicago, Illinois

Page 11 of 12273 listings

49 Passenger 72' Chris Craft - Perfect for Events!
Events in Chicago · 49 guests

49 Passenger 72' Chris Craft - Perfect for Events!

New
Superowner
$1,350/hour
Sea Ray Sundancer 290 - Luxury Yacht Rental in Chicago for Events
Events in Chicago · 10 guests

Sea Ray Sundancer 290 - Luxury Yacht Rental in Chicago for Events

New
$325/hour
52' Azimut Fly 50 Motor Yacht Rental in Chicago IL
Events in Chicago · 13 guests

52' Azimut Fly 50 Motor Yacht Rental in Chicago IL

New
$1,000/hour
Explore the Waves with Ease! Rent Your Dream Boat Today!
Events in Chicago · 11 guests

Explore the Waves with Ease! Rent Your Dream Boat Today!

New
$275/hour
No tie ups - 40ft Premium Yacht - lots of room group of for 12 - DuSable Harbor
Events in Chicago · 12 guests

No tie ups - 40ft Premium Yacht - lots of room group of for 12 - DuSable Harbor

New
$250/hour
31ft Cabin Cruiser Belmont Harbor location
Events in Chicago · 6 guests

31ft Cabin Cruiser Belmont Harbor location

New
$300/hour
Luxury 33' Sea Ray Yacht Rental in Chicago
Events in Chicago · 10 guests

Luxury 33' Sea Ray Yacht Rental in Chicago

New
$250/hour
Hey Chicago, Climb Aboard Our 33' Cruiser Motor Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Hey Chicago, Climb Aboard Our 33' Cruiser Motor Yacht in Chicago, Illinois

New
$350/hour
Monterey 256 Cruiser!
Powerboats in Chicago · 6 guests

Monterey 256 Cruiser!

New
$250/hour
Scenic Lake Michigan Cruises on a 35’ Formula Sun Sport
Events in Chicago · 12 guests

Scenic Lake Michigan Cruises on a 35’ Formula Sun Sport

New
$300/hour
Charter Fishing or Pleasure Boat Lake Michigan, Captain Included
Fishing in Chicago · 6 guests

Charter Fishing or Pleasure Boat Lake Michigan, Captain Included

New
$275+/hour
Chicago Waterfront Adventures aboard Regal Commodore 38ft
Events in Chicago · 12 guests

Chicago Waterfront Adventures aboard Regal Commodore 38ft

New
$300/hour
Come Cruise the waters around Chicago with 33ft Motor Yacht
Powerboats in Chicago · 6 guests

Come Cruise the waters around Chicago with 33ft Motor Yacht

New
$325/hour
Classic 43ft Hatteras w/Captain Included in Hourly Rate (Chicago)
Events in Chicago · 6 guests

Classic 43ft Hatteras w/Captain Included in Hourly Rate (Chicago)

New
$300+/hour
Luxury Unleashed – 40ft Sea Ray Dream Cruiser
Events in Chicago · 12 guests

Luxury Unleashed – 40ft Sea Ray Dream Cruiser

New
$350/hour
Oceanis 393 Beneteau Sailing Yacht Rental in Chicago
Sailing in Chicago · 10 guests

Oceanis 393 Beneteau Sailing Yacht Rental in Chicago

New
$275/hour
High Performance Luxury Fountain 43 Center Console
Powerboats in Chicago · 12 guests

High Performance Luxury Fountain 43 Center Console

New
$775+/hour
Willard Marine SeaForce!! Former Military Adventure Boat!
Powerboats in Chicago · 6 guests

Willard Marine SeaForce!! Former Military Adventure Boat!

New
$270/hour
40ft Yacht - Formula Fast - Get to the Play Pen in 10 mins
Powerboats in Chicago · 12 guests

40ft Yacht - Formula Fast - Get to the Play Pen in 10 mins

New
$200/hour
63' Luxury Yacht - Classic Chris Craft with Exquisite Style
Events in Chicago · 13 guests

63' Luxury Yacht - Classic Chris Craft with Exquisite Style

New
$950/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
Snoozed - Active 02 Oct 2025
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
Superowner
Snoozed - Active 02 Nov 2025
27 ft Sea Ray, Captain Included
Events in Chicago · 8 guests

27 ft Sea Ray, Captain Included

5.0
Snoozed - Active 02 Jan 2026
Spacious Crusing Yacht 40' on the Chicago Lakefront $275.00 per Hour Weekdays
Events in Chicago · 12 guests

Spacious Crusing Yacht 40' on the Chicago Lakefront $275.00 per Hour Weekdays

5.0
Snoozed - Active 27 Sep 2025

Chicago Reviews

  1. EW

    Emily

    27 ft Sea Ray, Captain Included

    We had the best time on Bobby's boat! He was very responsive and responsible. Vibes were awesome and he took good care of us when the water conditions were a little challenging. We had a ton of fun, thank you!

  2. KA

    Kelly

    27 ft Sea Ray, Captain Included

    Bobby was the best captain! We left right on time and the water was beautiful. He had a cooler with ice prepared and ready for us upon arrival, and made the whole trip a time to remember! I could not recommend him enough!

  3. DJ

    Dana

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

    We had an absolutely unforgettable boating experience. Adnan's larger boat was amazing, very spacious and it provided plenty of room to relax. We have amazing pictures to cherish from our time on board. Our captain was fantastic as well. We enjoyed his company. Additionally, the owner was incredibly accommodating when we had a change in plans, making the experience even smoother. We can't wait to book another outing—highly recommended for anyone seeking a memorable day on the water!

  4. AS

    Azam

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

    I can’t recommend these guys enough. From the moment we pulled up to the boat to the time got off, we were taken care of with 5 star service. I am particularly impressed with how they cared for my 3 children as they ran around the boat and ignored all the rules lol I sincerely appreciate the patience! We cruised from the Chicago yacht club down the Chicago river. We stopped at pizzeria portofinos for dinner and ate on the boat. It was an awesome experience. I can’t wait to book with Adnan and his crew again!!!! Next time with friends and no kids!

  5. FM

    Francesca

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

    I recently had the pleasure of chartering this boat in Chicago to explore the stunning beauty of Lake Michigan, and let me tell you, it was an experience that exceeded all expectations. From start to finish, our time aboard this boat was fantastic. Nothing short of extraordinary, leaving me and my friends with lifelong memories and an insatiable desire to return. Allow me to share with you why this boat charter deserves the most resounding rave review. First and foremost, the boat itself was marvelous. Every detail was carefully considered, from the plush seating areas to the spacious deck that provided panoramic views of the mesmerizing lake and play pen. The boat's cleanliness and attention to detail spoke volumes about the dedication our captain had to ensure an unforgettable experience. Speaking of the captain, he was the true star of this adventure. From the moment we stepped on board, we were greeted with warmth and professionalism. His expertise and passion for boating were evident as he guided us through safety protocols. His genuine enthusiasm for his work elevated the entire experience, making us feel like cherished guests on a remarkable voyage. The highlight of the charter was undoubtedly the breathtaking views of Lake Michigan and the stunning Chicago skyline. As we cruised along the glistening waters, the boat provided the perfect vantage point to admire the majesty of the city and river. We are so grateful for countless photo opportunities and creating cherished memories. Whether we were seeking relaxation or excitement, the boat catered to our desires. We had the option to bask in the sun, feel the gentle breeze against our skin, and soak in the tranquility of the open waters. From the seamless booking process to the thoughtfully curated river tour and play pen jaunt, every element was carefully orchestrated to ensure our absolute satisfaction. Thank you for creating an unforgettable experience. In conclusion, our charter boat experience in Chicago on Lake Michigan was an absolute dream come true. The boat's exquisite design, the professionalism of the captain, the awe-inspiring views, the array of activities, combined to create an adventure that far exceeded my wildest expectations. If you're seeking a remarkable and unforgettable journey, I wholeheartedly recommend chartering this boat on Lake Michigan. Trust me, you won't be disappointed.

  6. JW

    Jacqueline

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

    We can highly recommend a boat trip with Adnan and his team. The boat is very modern and offers a lot of comfort. The captain was very skilled, supportive and a nice personality. We very much enjoyed the trip on the River, what an experience and memory to take home! The administrative process was very smooth and the owner replied immediately to all the questions. We would book this service again anytime. Good luck to the owner and the crew in the future!