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    Captain

    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (4,233 Reviews)

    Page 3 of 11 • 261 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    Downtown Chicago, Party on the Lake!
    Powerboats in Chicago · 10 guests

    Downtown Chicago, Party on the Lake!

    4.9
    $270hour
    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
    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
    50 ft Double Decker Yacht | Sea Ray Bridge Express
    Events in Chicago · 12 guests

    50 ft Double Decker Yacht | Sea Ray Bridge Express

    5.0
    $100person
    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
    55' Sea Ray Luxury Yacht in Chicago
    Events in Chicago · 12 guests

    55' Sea Ray Luxury Yacht in Chicago

    5.0
    $325hour
    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
    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
    33ft Day Boat in Chicago
    Events in Chicago · 10 guests

    33ft Day Boat in Chicago

    4.9
    $275hour
    46ft Prestige Flybridge Luxury Yacht in Chicago
    Events in Chicago · 13 guests

    46ft Prestige Flybridge Luxury Yacht in Chicago

    4.9
    Best of 2023
    $400hour
    "Excelling in Excellence" Yacht Charter in Chicago, IL
    Events in Chicago · 13 guests

    "Excelling in Excellence" Yacht Charter in Chicago, IL

    New
    $772hour
    NEW!!! 35' Luxury Motor Yacht with 4’ swim platform in Chicago
    Events in Chicago · 12 guests

    NEW!!! 35' Luxury Motor Yacht with 4’ swim platform in Chicago

    5.0
    $180-$270hour
    Multi Level 47' Carver Yacht for 12 Guests in Chicago, IL - Best Value! (MPY#3)
    Events in Chicago · 12 guests

    Multi Level 47' Carver Yacht for 12 Guests in Chicago, IL - Best Value! (MPY#3)

    4.8
    Superowner
    $350hour
    SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois

    5.0
    $275hour
    27 Sea Ray Sundancer Pre Season specials playpen party
    Events in Chicago · 8 guests

    27 Sea Ray Sundancer Pre Season specials playpen party

    5.0
    $180hour
    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)
    Events in Chicago · 12 guests

    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

    5.0
    Superowner
    Best of 2023
    $250hour
    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!
    Powerboats in Chicago · 12 guests

    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!

    4.8
    Superowner
    $250hour
    40ft Boat w/ HUGE open seating area!
    Events in Chicago · 12 guests

    40ft Boat w/ HUGE open seating area!

    5.0
    Superowner
    Best of 2023
    $210-$240hour
    Amazing Party Trips on 34ft Cruiser in Chicago
    Events in Chicago · 16 guests

    Amazing Party Trips on 34ft Cruiser in Chicago

    4.9
    Superowner
    $425hour
    Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago
    Events in Chicago · 11 guests

    Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago

    4.8
    Superowner
    $350hour
    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
    Events in Chicago · 10 guests

    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

    5.0
    $500hour

    Chicago Reviews

    1. 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.

    2. Jenna

      Jenna

      50 ft Double Decker Yacht | Sea Ray Bridge Express

      Great boat with good communication. Didn't love the captain but that was separate.

    3. 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!

    4. TT

      Tyler

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

      I can’t understate how incredible Captain Bob is at what he does. He’s not only Incredibly knowledgeable but strives to make memorable moments during his trips. We booked a 2 hour boat ride, 1 hour speed boat and another hour sunset tour. Captain Bob set us up for multiple mini photo shoots with the perfect backdrops and took the pictures himself. An incredible value for the cost. He made my birthday extremely special. Thank you Captain Bob!!

    5. CG

      Clare

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

      Captain Bob is the GOAT! We love him! He was so accommodating and so much fun. He took us out on the lake and gave us a sight seeing tour. My guests from out of town had so much fun being on lake. He took us to see the Chicago lighthouse, Navy Pier, Planetarium, and Play Pen. Would definitely recommend!!

    6. VH

      Valerie

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

      We had a brilliant time with Captain Bob - even though the boat is a speed demon (in a good way), he's got a background doing water rescues as a firefighter so we always felt like we were in safe hands. He's also got an encyclopaedic knowledge of Chicago history and some interesting stories about the city. He's also great at stopping at the scenic spots for the most memorable photos. Loved our trip - can't wait to go again some time.

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