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Rent a Boat or Yacht in Chicago, Illinois

Page 2 of 12269 listings

UP to  20 passengers Party Boat - Chicago Playpen or River trips
Powerboats in Chicago · 20 guests

UP to 20 passengers Party Boat - Chicago Playpen or River trips

5.0
Superowner
Best of 2023
$120person
50' Multi-level Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

50' Multi-level Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2023
$350hour
Instant Book
Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED
Events in Chicago · 7 guests

Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

5.0
$300hour
Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago
Events in Chicago · 13 guests

Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago

5.0
Superowner
$275hour
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$150hour
37' Luxury Sailboat with Captain in Chicago, Illinois
Sailing in Chicago · 10 guests

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0
Superowner
$299hour
*** $199 hr***Weekend Charter Rental - 33' Maxum!
Events in Chicago · 10 guests

*** $199 hr***Weekend Charter Rental - 33' Maxum!

4.8
$175hour
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
$275-$300hour
Instant Book
14 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 14 guests

14 Passenger Captained Party & Event Boat in Chicago, Illinois!

5.0
Superowner
Best of 2023
$600hour
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
$300hour
25ft Rinker - Captained Party - Chicago
Powerboats in Chicago · 6 guests

25ft Rinker - Captained Party - Chicago

4.9
Superowner
$180hour
Sea Ray Express 390 Luxury Charter in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0
$300hour
40ft Yacht w/ Huge open seating area!
Powerboats in Chicago · 12 guests

40ft Yacht w/ Huge open seating area!

5.0
Superowner
Best of 2023
$210-$240hour
42FT Regal Commodore Express Cruiser
Events in Chicago · 12 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2023
$245-$275hour
Cruisers Yachts 35' - Chicago Playpen and River!
Powerboats in Chicago · 10 guests

Cruisers Yachts 35' - Chicago Playpen and River!

4.9
$280hour
Sea Ray 38 Sundancer - Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray 38 Sundancer - Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
Best of 2023
$400hour
Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior
Events in Chicago · 12 guests

Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior

5.0
Superowner
Best of 2023
$245-$275hour
42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago
Events in Chicago · 11 guests

42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

5.0
Superowner
$400hour
Maxum Yacht 44' in Chicago
Events in Chicago · 13 guests

Maxum Yacht 44' in Chicago

5.0
Superowner
Best of 2023
$268-$300hour
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
$250hour
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
$400hour
Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties
Events in Chicago · 12 guests

Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

5.0
Best of 2023
$400hour
Instant Book
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$115-$120hour
44' Luxury Sundancer Yacht Rental! Includes Floating Island!
Events in Chicago · 12 guests

44' Luxury Sundancer Yacht Rental! Includes Floating Island!

4.8
Superowner
$399hour

Chicago Reviews

  1. AT

    Abby

    UP to 20 passengers Party Boat - Chicago Playpen or River trips

    Greg was awesome! Everything about our experience was SO easy. They were ready right when we arrived and the boat was clean and ready to go with ice in the cooler. He knew exactly where to go since it was too windy that day and we could not go to play pen. He directed us towards the "second" playpen by the planetarium where all the other boats were. AMAZING DAY!! cannot say enough great things about it, will be booking again.

  2. JC

    Jenny

    UP to 20 passengers Party Boat - Chicago Playpen or River trips

    Greg is great! He was a quick communicator from the start of my boat rental search. The boat was clean and a great size. Greg provides ice and a cooler as well as Bluetooth speakers. He took us on a beautiful sunset ride with amazing views of the skyline. Everyone enjoyed their experience and we will definitely book with him again!

  3. FT

    Frances

    UP to 20 passengers Party Boat - Chicago Playpen or River trips

    We had an amazing time with Captain Greg for a bachelorette party! The boat is spacious and well-equipped (bathroom, great speaker system, float for the water), and we appreciated that he had a large cooler and ice waiting for us upon our arrival. The entire booking process was easy and we appreciated Captain Greg's constant communication leading up to our trip.

  4. Kayla

    Kayla

    50' Multi-level Luxury Yacht with Party up to 12

    Will definitely be booking again! I celebrated my 24th birthday with some friends and it was an amazing experience. The owner responded quickly and answered ALL questions. The price was great for 4 hours on a BEAUTIFUL day and the Debonair was exactly as pictured! Captain Jim was amazing! We enjoyed talking and learning from him! Do not hesitate to book!!

  5. Amanda

    Amanda

    50' Multi-level Luxury Yacht with Party up to 12

    First let me say how kind, funny and accommodating Captain Jim is. He explained everything we needed to know. He provided us with ice and water. He took an amazing route along the lake! The vessel itself is beautiful. Comfortably accommodating for 12 ppl. We had the 7p-11p sail and was able to catch the fireworks at the end of the night. 10/10! We’ll definitely be booking again!

  6. NL

    Nate

    50' Multi-level Luxury Yacht with Party up to 12

    Great boat and captain! We loved the experience. Overall, best trip yet. Just make a note that the captain "tip and fee" are not included in the quote and when we heard from the captain he was cool and explained why - but it was quite misleading to not read this in the quote or listing somewhere ahead of time. We were sent the "fine print" about the laws around this after the fact. Just be aware. Overall, great choice for a boat and captain and we'd book them again. Thanks!