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Rent a Boat or Yacht in Chicago, Illinois

Page 2 of 12270 listings

Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED
Events in Chicago · 7 guests

Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

5.0
$300hour
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
36' Sundancer in Chicago
Events in Chicago · 13 guests

36' Sundancer in Chicago

5.0
$240-$250hour
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
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
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
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
35' Searay Sundancer Best Party Boat in Chicago, Illinois
Events in Chicago · 11 guests

35' Searay Sundancer Best Party Boat in Chicago, Illinois

5.0
$395hour

Chicago Reviews

  1. JS

    Jess

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    Joe and Ryan provided a great experience for our bachelorette outing! We went to the playpen area and anchored. They were professional but fun and very attentive with anything we needed throughout the boat trip. They were able to accommodate our early departure request due to bad weather in the afternoon. Definitely recommend!

  2. KC

    Kira

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    Captain Joe was great! Very professional and experienced. He was happy to take us wherever we wanted to go and also gave us advice on the best places to stop and swim. The boat was just like in the pictures, clean and very comfortable. We loved the 6 person float that Captain Joe supplied for us. We would definitely book with him again!

  3. Colleen

    Colleen

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    Captain Joe was easy to communicate with and answered all my questions about our boat outing! He took endless pictures for us, provided detailed information about boat safety, and had a great raft for us to use. Would give our trip on Joe's boat a 10 out of 10! We will be doing it again!

  4. Lalique

    Lalique

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    Hands down one of my best boat rental experiences!! My girlfriends and I rented Captain Joe’s boat to celebrate our collective quarantine Birthdays and from start to finish the process was very easy. We arrived and Captain Joe was there to great us. He was so helpful and went over the boat and safety practices, which was easy. The boat was better that expected, clean, and had no issues. My girls and I were able to enjoy the beautiful scenery of the city, the landscaping and landmarks. It was breathtaking. We packed snacks and brought a mini cooler with drinks, and Captain Joe had his own big cooler ready to go with ice. It was a great time !! We will definitely be returning for more amazing memories. Highly recommended!!

  5. KV

    Kelsey

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    Captain Joe was the best! He was easy and quick to communicate with, told us where to park and meet him (all very close by), and he organized the trip so that the itinerary was exactly what we wanted (anchor and swim). He had floaties and noodles ready for us, a cooler for our food and drinks, and there was shade on the boat! He was chatty when we had questions but otherwise kept to himself so we could enjoy the trip. It was all so seamless and easy and you couldn't beat the boat, the weather, and the views of downtown Chicago. This was one of our Chicago highlights and I can't wait to come back and do it again.

  6. BK

    Brianna

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    Had a great time on Joe’s boat. He had a raft and cooler with ice for us ready to go. Also the speaker set up was clutch - hooks up to your iPhone and chargers. Back of the boat has a table for lunch and shade, front and very back perfect for being in sun. Washroom worked well. Joe was a greater communicator and very accommodating. Will def use again next boat trip out!