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    Captain

    Browse Lake Michigan Boat Rentals

    4.9
    (4,432 Reviews)

    Page 2 of 13 • 297 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
    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
    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
    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
    25ft Rinker - Captained Party - Chicago
    Powerboats in Chicago · 6 guests

    25ft Rinker - Captained Party - Chicago

    4.9
    Superowner
    $200hour
    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
    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
    Events in Chicago · 12 guests

    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

    4.9
    Superowner
    Best of 2023
    $250hour
    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
    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
    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
    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
    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
    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
    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
    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
    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
    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 Playpen and River cruises! 35’
    Powerboats in Chicago · 10 guests

    Chicago Playpen and River cruises! 35’

    4.9
    $295hour
    Sea Ray 40ft - Luxurious, Spacious, Affordable
    Events in Chicago · 12 guests

    Sea Ray 40ft - Luxurious, Spacious, Affordable

    4.9
    $250hour
    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
    Maxum Yacht 44' in Chicago
    Events in Chicago · 13 guests

    Maxum Yacht 44' in Chicago

    5.0
    Superowner
    Best of 2023
    $268-$300hour
    42FT Regal Commodore Express Cruiser
    Events in Chicago · 12 guests

    42FT Regal Commodore Express Cruiser

    5.0
    Superowner
    Best of 2023
    $245-$275hour

    Lake Michigan Reviews

    1. Kayla

      Kayla

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

      After previously dealing with an unresponsive host for another listing, Edward & Team made the experience a 10/10 for us with how promptly they were able to accommodate and communicate. Communication was excellent, Captain Jim was amazing, and the boat was absolutely stunning. We had such an amazing time, and will definitely be renting this boat again in the future.

    2. Anthony

      Anthony

      Maxum Yacht 44' in Chicago

      Chris and Captain Kelly were great all around from initial booking, communication leading up to the trip, and of course the trip itself. Highly recommended for any trips in the Chicago area!

    3. PK

      Pavel

      Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

      The trip was awesome. The boat is great and powerful, Robert knows a lot about Chicago. Absolutely recommended.

    4. 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 :)

    5. 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!

    6. EG

      Emily

      25ft Rinker - Captained Party - Chicago

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

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