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    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (4,189 Reviews)

    Page 2 of 12 • 269 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    36' Sundancer in Chicago
    Events in Chicago · 13 guests

    36' Sundancer in Chicago

    5.0
    $240-$250hour
    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
    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
    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
    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
    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
    33' Formula Motor Yacht - Great for Playpen!
    Events in Chicago · 10 guests

    33' Formula Motor Yacht - Great for Playpen!

    5.0
    $150hour
    25ft Rinker - Captained Party - Chicago
    Powerboats in Chicago · 6 guests

    25ft Rinker - Captained Party - Chicago

    4.9
    Superowner
    $180hour
    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
    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
    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
    Maxum Yacht 44' in Chicago
    Events in Chicago · 13 guests

    Maxum Yacht 44' in Chicago

    5.0
    Superowner
    Best of 2023
    $268-$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
    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
    Chicago Playpen and River cruises! 35’
    Powerboats in Chicago · 10 guests

    Chicago Playpen and River cruises! 35’

    4.9
    $295hour
    62' $2M Italian Luxury Yacht with Party up to 12
    Events in Chicago · 12 guests

    62' $2M Italian Luxury Yacht with Party up to 12

    5.0
    Superowner
    Best of 2023
    $800hour
    Instant Book

    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. MK

      Mitali

      36' Sundancer in Chicago

      We had a great time celebrating a birthday with 13 friends. Pete was very communicative, the boat was beautiful and the day out on the lake was perfect! The dock was easy to locate for our large group. The crew provided floats to use in the water when we were swimming and a cooler for our drinks. They were so helpful the entire time, offering to assist us when we were moving from the front to back of the boat. Overall amazing experience and we recommend to anyone looking for the perfect Chicago boat day!

    5. 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.

    6. 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!

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