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    Browse Lake Michigan Boat Rentals

    4.9
    (4,566 Reviews)

    Page 3 of 15 • 353 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    SuMmer Fun and RiDing the WaVes
    Water Sports in Portage · 3 guests

    SuMmer Fun and RiDing the WaVes

    5.0
    $375-$500day
    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
    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
    40ft Chris Craft for Fishing or Cruising on Lake Michigan
    Fishing in Racine · 6 guests

    40ft Chris Craft for Fishing or Cruising on Lake Michigan

    5.0
    $145hour
    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
    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
    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
    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
    $200day
    24 Foot Robalo on Lake Michigan, with bathroom!
    Powerboats in Milwaukee · 12 guests

    24 Foot Robalo on Lake Michigan, with bathroom!

    5.0
    $125hour
    46' Spacious Portofino Party Yacht in Chicago For Every Occasion
    Events in Chicago · 12 guests

    46' Spacious Portofino Party Yacht in Chicago For Every Occasion

    5.0
    $250hour
    Diversey Harbor 46 ft Luxury Yacht Sun Dancer
    Events in Chicago · 12 guests

    Diversey Harbor 46 ft Luxury Yacht Sun Dancer

    5.0
    $200hour
    44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
    Events in Chicago · 13 guests

    44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois

    4.9
    Superowner
    $399hour
    33ft Day Boat in Chicago
    Events in Chicago · 10 guests

    33ft Day Boat in Chicago

    4.9
    $275hour

    Lake Michigan Reviews

    1. Kaitlin

      Kaitlin

      44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois

      Highly recommend! Jimmy was very nice and he even rescheduled us to the following day due to bad weather. He made my birthday very special and I would definitely book with him again in the future!

    2. EG

      Emily

      25ft Rinker - Captained Party - Chicago

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

    3. MC

      Megan

      37' Luxury Sailboat with Captain in Chicago, Illinois

      Greg was an amazing captain - he sent a very helpful document that outlined all the details about the boat ahead of time, he was on time and willing to be flexible in wherever we wanted to go. We had an amazing time and I would definitely hire him again!

    4. Sara

      Sara

      37' Luxury Sailboat with Captain in Chicago, Illinois

      My fiancé and I planned a engagement photoshoot, however, due to weather conditions not cooperating, Greg was so flexible at rescheduling with us. He made us feel very comfortable and gave tips on how to take the most beautiful photoshoot out of the beautiful scenery of the city. Would totally recommend him! By the way, the boat was spotless, so clean and so so beautiful😍

    5. GM

      Gerald

      37' Luxury Sailboat with Captain in Chicago, Illinois

      We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.

    6. Bailey

      Bailey

      37' Luxury Sailboat with Captain in Chicago, Illinois

      We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with taking the photos and positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.

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