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02/17/2024  ± 1 day

Rent a Boat or Yacht in Chicago, Illinois

Page 2 of 12270 listings

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

4.7
Superowner
$300hour
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
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
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
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
**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
Superowner
Best of 2023
$250hour
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
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
25ft Rinker - Captained Party - Chicago
Powerboats in Chicago · 6 guests

25ft Rinker - Captained Party - Chicago

4.9
Superowner
$180hour
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$150hour
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
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
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
42FT Regal Commodore Express Cruiser
Events in Chicago · 12 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2023
$245-$275hour
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
Maxum Yacht 44' in Chicago
Events in Chicago · 13 guests

Maxum Yacht 44' in Chicago

5.0
Superowner
Best of 2023
$268-$300hour
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
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
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
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
Snoozed - Active 03 Feb 2025
Chicago Playpen and River cruises! 35’
Powerboats in Chicago · 10 guests

Chicago Playpen and River cruises! 35’

4.9
$300hour
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

Chicago Reviews

  1. SA

    Suchi

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

    Celebrated my birthday on the water and watched the fireworks! A memorable trip with my friends :)

  2. SA

    Suchi

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

    Great trip and excellent service! Had such a fun time with my girlfriends on the water!

  3. EG

    Emily

    25ft Rinker - Captained Party - Chicago

    Had the best time! Joe was super helpful and super fun!

  4. cp

    cecile

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

    Loved our experience with Troy! We had a party of 13 and the boat was a perfect size for our group. Captain Charlie and first mate Anton were professional and we had a perfect afternoon out on the lake. Highly recommended!! We want to do this every summer!

  5. AA

    Amanda

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

    Captains Charlie and Laura were excellent hosts and made our afternoon work outing on the lake a blast! They setup the coolers and food table then took us up and down the lakefront for beautiful views of the city. Excellent communication and directions from Troy. Highly recommend this company and would definitely use them again. Cheers!

  6. Kelsey

    Kelsey

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

    I highly recommend tail gate of the lake. I booked them for my bachelorette party. We all had such a good time. The boat was clean and the captain and co captain were so helpful & nice! They made sure we had a good time & we definitely did. The booking process was easy and I had communication with the owner for any questions I had.