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    Captain

    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (4,197 Reviews)

    Page 2 of 11 • 258 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    70' EXCLUSIVE Motor Yacht NEW to Chicago
    Events in Chicago · 13 guests

    70' EXCLUSIVE Motor Yacht NEW to Chicago

    4.8
    Superowner
    $999hour
    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
    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED
    Events in Chicago · 7 guests

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    5.0
    $285-$350hour
    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
    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
    Maxum Yacht 44' in Chicago
    Events in Chicago · 13 guests

    Maxum Yacht 44' in Chicago

    5.0
    Superowner
    Best of 2023
    $268-$300hour
    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
    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
    Diversey Harbor 46 ft Luxury Yacht Sun Dancer
    Events in Chicago · 12 guests

    Diversey Harbor 46 ft Luxury Yacht Sun Dancer

    5.0
    $200hour
    25ft Rinker - Captained Party - Chicago
    Powerboats in Chicago · 6 guests

    25ft Rinker - Captained Party - Chicago

    4.9
    Superowner
    $199hour
    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
    42FT Regal Commodore Express Cruiser
    Events in Chicago · 12 guests

    42FT Regal Commodore Express Cruiser

    5.0
    Superowner
    Best of 2023
    $245-$275hour
    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
    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
    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
    33ft Day Boat in Chicago
    Events in Chicago · 10 guests

    33ft Day Boat in Chicago

    4.9
    $275hour
    Sea Ray 45' Chicago Playpen, River, Winery, Lilly Pad
    Events in Chicago · 12 guests

    Sea Ray 45' Chicago Playpen, River, Winery, Lilly Pad

    5.0
    Superowner
    Best of 2023
    $375-$450hour
    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
    "Excelling in Excellence" Yacht Charter in Chicago, IL
    Events in Chicago · 13 guests

    "Excelling in Excellence" Yacht Charter in Chicago, IL

    New
    $772hour
    36' Sundancer in Chicago
    Events in Chicago · 13 guests

    36' Sundancer in Chicago

    5.0
    $240-$250hour

    Chicago Reviews

    1. 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!

    2. Victor

      Victor

      36' Sundancer in Chicago

      Excellent captain and very knowledgeable and friendly. We had a great time and conversed on many interesting topics related to Chicago and the lake. I definitely recommend him.

    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. JD

      Jennifer

      70' EXCLUSIVE Motor Yacht NEW to Chicago

      We had the absolute best time on our 4 hour trip!! I wish we would’ve booked for longer honestly. Where to even start? The yacht is even more beautiful in person with so much space that you have to choose to hang out in different spaces. The crew (Damien and Monica) were PERFECTION. they were so helpful, kind, and attentive to whatever we needed or wanted to do. We fully plan to book again! Thank you so much!

    5. AB

      Alexis

      Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

      So so fun for a bunch of 30 year olds! There was a little confusion on the morning of- the owner got confused and accidentally canceled the booking. But he was very communicative with the technical error and really great to work with. Great bang for your buck!

    6. 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!

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