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Browse Illinois Boat Rentals.

Page 2 of 7167 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
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
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
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$200/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
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
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
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200/hour
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
Best of 2023
$225/hour
37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen
Events in Chicago · 12 guests

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

New
Best of 2023
$250/hour
31' Sea Ray Romantic or Family or Fun Getaway  Waiting for you !!!
Events in Chicago · 6 guests

31' Sea Ray Romantic or Family or Fun Getaway Waiting for you !!!

5.0
$300/hour
Downtown Chicago, Party on the Lake!
Powerboats in Chicago · 10 guests

Downtown Chicago, Party on the Lake!

4.9
$270/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
$300/hour
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 2023
$180/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
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
Best of 2023
$250/hour
25ft Rinker - Captained included in price- Chicago
Powerboats in Chicago · 6 guests

25ft Rinker - Captained included in price- Chicago

4.9
Superowner
$160/hour
27 Sea Ray Sundancer DM for October specials
Events in Chicago · 8 guests

27 Sea Ray Sundancer DM for October specials

5.0
$180/hour

Illinois Reviews

  1. Stephaughn

    Stephaughn

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

    I recently had the pleasure of spending a day aboard this beautiful yacht, and it truly exceeded my expectations. From the moment we arrived, we were welcomed with warm hospitality by a professional and attentive crew. They made sure every detail was taken care of, ensuring our comfort throughout the day. The yacht itself is stunning—luxuriously designed, well-maintained, and spacious enough to accommodate our group comfortably. The interiors are elegant and equipped with every amenity we could possibly need. The outdoor areas are perfect for lounging, dining, and taking in the breathtaking views. Our time on the yacht was both relaxing and memorable, thanks to the crew’s excellent service and the captain’s expertise in navigating the local waters. They took us to the most beautiful and serene spots, making the experience even more special. Overall, our day on the yacht was truly wonderful. I highly recommend this yacht for anyone looking for an unforgettable experience on the water. We’re already looking forward to our next adventure on board.

  2. 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!!

  3. SK

    Sai

    27' Chris Craft with Water Toys plus Jet Ski Available

    Our experience with Captain Tim Jr was incredible! He is a fantastic captain, the boat was awesome, and he battled a storm to get us to the fountain, I proposed to my girlfriend, and he battled the storm right back to the dock. An experience we will never forget, best captain you could ask for!

  4. MR

    Milena

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

    My bachelorette crew and I had a phenomenal time out on the water. Weather was great, vessel was great, and we made some lifelong memories! Will definitely be back on the waters of Lake Michigan soon. An activity worth doing if you’re making a trip to Chicago.

  5. MG

    Michelle

    Chicago Summer Vibes - Soak up the Sun in Style!

    Dan is the best!! Extremely nice and communicative. The boat is even nicer in person and was extremely clean and cool looking. Big cooler to fit drinks and food and snacks. Great music sound system. Would highly recommend Dan and his boat to anyone.

  6. Andrew

    Andrew

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

    Our group had a great time! I would recommend using Nicole for your sailing trip!