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Winnetka, Illinois Boat Rentals

Page 1 of 124 listings

Premium 28' Larson Cabrio with Ultra Loud Speakers and the Ultimate Inflatable
Events in Chicago · 8 guests

Premium 28' Larson Cabrio with Ultra Loud Speakers and the Ultimate Inflatable

New
$275/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
LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)
Events in Chicago · 13 guests

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

5.0
Superowner
Best of 2025
$250/hour
Flawless 2024 68' Sunseeker Manhattan
Events in Chicago · 12 guests

Flawless 2024 68' Sunseeker Manhattan

New
Snoozed - Active 02 Jan 2026
40ft Formula 40 Performance Cruiser in Chicago
Tours in Chicago · 13 guests

40ft Formula 40 Performance Cruiser in Chicago

5.0
$349/hour
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Events in Chicago · 13 guests

44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available

5.0
Superowner
$575+/hour
46' Luxury Yacht! Price all inclusive!
Events in Chicago · 6 guests

46' Luxury Yacht! Price all inclusive!

5.0
Snoozed - Active 17 Apr 2026
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
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
$250/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
$250/hour
31ft Cabin Cruiser Belmont Harbor location
Events in Chicago · 6 guests

31ft Cabin Cruiser Belmont Harbor location

New
$300/hour
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
$1,500/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

4.8
$245/hour
Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
Events in Chicago · 13 guests

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

4.9
Superowner
Best of 2025
$250/hour
32ft SeaRay Sundancer for Charter in Chicago
Events in Chicago · 6 guests

32ft SeaRay Sundancer for Charter in Chicago

5.0
$300/hour
Beautiful 31ft Sports Craft Boat With All The Amenities Down Below
Fishing in Chicago · 6 guests

Beautiful 31ft Sports Craft Boat With All The Amenities Down Below

New
Superowner
$200/hour
Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.
Powerboats in Chicago · 6 guests

Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.

5.0
$225+/hour
Capt. Included - 10 Passengers - 27' Bayliner Ciera Charter Boat
Powerboats in Chicago · 10 guests

Capt. Included - 10 Passengers - 27' Bayliner Ciera Charter Boat

New
$248/hour
27 ft Sea Ray, Captain Included
Events in Chicago · 5 guests

27 ft Sea Ray, Captain Included

5.0
Snoozed - Active 02 Jan 2026
27 Sea Ray Sundancer September specials! $130 hr
Events in Chicago · 8 guests

27 Sea Ray Sundancer September specials! $130 hr

5.0
$155+/hour
New 40 ft Regal luxury Yacht Sept promotion $250 hr
Events in Chicago · 12 guests

New 40 ft Regal luxury Yacht Sept promotion $250 hr

New
$260+/hour
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
$200/hour
25ft Rinker - Captained included in price- Chicago
Powerboats in Chicago · 8 guests

25ft Rinker - Captained included in price- Chicago

4.9
Superowner
$199/hour
42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR
Events in Chicago · 12 guests

42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR

4.0
$150/hour
Instant Book

Winnetka Reviews

  1. LH

    Liz

    25ft Rinker - Captained included in price- Chicago

    We had a great day on the water with Joe! Fast and friendly responses, affordable and straightforward pricing, and a free great comfortable boat with everything we needed. Highly recommend!

  2. NV

    Natalie

    25ft Rinker - Captained included in price- Chicago

    Highly recommend Joe and his boat! He made my birthday so special. The boat is equipped with everything you may need - ice and a cooler. And of course, all the toys for the water. The views were spectacular and he recommended doing a cruise before anchoring and getting in the water which we loved. The speaker is also so nice to listen to your favorite tunes!!

  3. Matthew

    Matthew

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

    The boat was great, fit our party of 12 well! Shay was communicative and flexible with the itinerary, and Captain Scott and Dave made our day on the boat a blast.

  4. MS

    Mollie

    25ft Rinker - Captained included in price- Chicago

    Joe and the boat is great. He was fast in responding and was very flexible in a last minute change in date due to weather conditions. A super special trip out for my mums 60th birthday! Thank you Joe!

  5. EL

    Emily

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

    The boat we originally booked (with a different company) cancelled our 10:00am departure at 8:30am. Elegija happened to have an opening and went out of her way to ensure we were able to book Island and Captain Joe for a 10:00am departure. We had the best time. Joe was great and the boat was comfortable. We will definitely book again.

  6. 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.