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Winnetka, Illinois Boat Rentals

24 listings
Montrose Boat rental in Chicago- EL Garifuna
Powerboats in Chicago · 5 guests

Montrose Boat rental in Chicago- EL Garifuna

5.0
$119hour
2022 BRIS BSK370 Dinghy for rent in Chicago, Illinois
Powerboats in Chicago · 1 guest

2022 BRIS BSK370 Dinghy for rent in Chicago, Illinois

New
$40hour
LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)
Events in Chicago · 12 guests

LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

5.0
Superowner
Best of 2023
$199hour
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

5.0
Superowner
Best of 2023
$230hour
44' Italian Luxury Azimut Premier Party Yacht up to 12 plus Jet Ski Available
Events in Chicago · 12 guests

44' Italian Luxury Azimut Premier Party Yacht up to 12 plus Jet Ski Available

5.0
Superowner
Best of 2023
$600hour
40ft Formula 40 Performance Cruiser in Chicago
Tours in Chicago · 13 guests

40ft Formula 40 Performance Cruiser in Chicago

5.0
Superowner
Best of 2023
$369hour
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 10 guests

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

5.0
Superowner
Best of 2023
$350hour
35' Sea Ray SLX Motor Yacht Charter in Chicago
Events in Chicago · 13 guests

35' Sea Ray SLX Motor Yacht Charter in Chicago

5.0
Superowner
Best of 2023
$369hour
46' Luxury Yacht! Price all inclusive!
Events in Chicago · 6 guests

46' Luxury Yacht! Price all inclusive!

5.0
$350hour
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Events in Chicago · 20 guests

Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

4.8
Best of 2023
$1,500hour
32ft SeaRay Sundancer for Charter in Chicago
Events in Chicago · 6 guests

32ft SeaRay Sundancer for Charter in Chicago

5.0
$300hour
Sail in Style: Fuel & Fun Included on 37' Four Winns 348 Vista Yacht!
Events in Chicago · 12 guests

Sail in Style: Fuel & Fun Included on 37' Four Winns 348 Vista Yacht!

4.3
$300hour
Luxury Awaits: 37' Four Winns 348 Vista Yacht with Gas & Lily Pad!
Events in Chicago · 12 guests

Luxury Awaits: 37' Four Winns 348 Vista Yacht with Gas & Lily Pad!

5.0
$300hour
Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
Events in Chicago · 12 guests

Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

4.9
Superowner
Best of 2023
$199hour
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
$230hour
Sea Ray Motor Yacht w/Hydraulic Swim Platform ($750 For 3hrs Mon-Thu & Sun)
Events in Chicago · 12 guests

Sea Ray Motor Yacht w/Hydraulic Swim Platform ($750 For 3hrs Mon-Thu & Sun)

3.0
$250hour
27 Sea Ray Sundancer  Pre Season specials playpen party
Events in Chicago · 8 guests

27 Sea Ray Sundancer Pre Season specials playpen party

5.0
$180hour
SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois

5.0
$300hour
Amazing Bowrider Rental in Chicago, Illinois
Powerboats in Chicago · 8 guests

Amazing Bowrider Rental in Chicago, Illinois

5.0
$300hour
25ft Crownline Cruiser Cuddy Cabin Boat Rental in Chicago, Illinois
Powerboats in Chicago · 6 guests

25ft Crownline Cruiser Cuddy Cabin Boat Rental in Chicago, Illinois

New
$300hour
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
$275hour
51ft Sea Ray Sundancer Yacht at Diversey Harbor!
Events in Chicago · 12 guests

51ft Sea Ray Sundancer Yacht at Diversey Harbor!

New
$500hour
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Events in Chicago · 5 guests

Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

5.0
Superowner
$200day
Doral Alegria 50' Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Doral Alegria 50' Yacht in Chicago, Illinois

5.0
$400hour

Winnetka Reviews

  1. HR
    Heidi
    Montrose Boat rental in Chicago- EL Garifuna

    I honestly have to say hands down the best experience renting a boat! The owner is a really great fit, and went above and beyond to help us with all of our questions and concerns. We will be using him again! I honestly don't think you can find better then Angel! Thank you again for everything! We had an amazing time!

  2. Sean
    Sean
    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    We spent a gorgeous afternoon on Lake Michigan. Rode along the skyline, best way to see the city. The booking process was very easy. Very attentive and quick to respond to any of my questions I had. We loved it so much we already booked it again for June and July.

  3. NA
    Nikol
    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    This yacht is exactly what we needed for our Chicago trip I took my perents on an afternoon cruise and it was amazing! Very spacious, the yacht has multiple levels and a really good sound system, we hung out at the Chicago playpen for a little bit and then went to the Chicago river, it was absolutely gorgeous Captain Joe was great

  4. bb
    bridget
    27' Chris Craft with Water Toys plus Jet Ski Available

    We booked a four hour trip for our family of four and absolutely loved it. We needed to reschedule our originally booked day due weather and Tim was very accommodating and flexible. Our experience on the water was perfect and exceeded our expectations for a family day out. I can’t wait to book again soon.

  5. DJ
    Dana
    27' Chris Craft with Water Toys plus Jet Ski Available

    Great experience! We had a wonderful and relaxing trip down the shore, taking amazing pictures. We really enjoyed just relaxing on the floatable and taking in the scenery. Tim was great too, communicating quickly and accommodating us when we parked in the wrong parking lot, causing us to be late. We would definitely rent with him again. It was an unforgettable day.

  6. Sabrae
    Sabrae
    27' Chris Craft with Water Toys plus Jet Ski Available

    Our boat ride with Captain Tim and first mate Diana was the perfect way to celebrate my husband‘s birthday. The boat accommodated the six of us perfectly allowing us to enjoy the ride together. We enjoyed the experience of going from the dock through the lake to the Chicago river and back. Captain Tim was able to expertly navigate the waters in spite of other boater’s behaving badly. We enjoyed Captain Tim allowing us to eat, drink and be merry for the whole ride. It was a beautiful night and he knew all the perfect spots for pictures. The next time I’m looking to rent a boat, Captain Tim will be my first choice!