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    All listings in Illinois

    Incredible tours in Illinois, United States.

    4.9
    (5,444 Reviews)

    Page 1 of 12 • 268 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Limited Availability
    29ft Sea Ray Sundancer Captained Boat In Chicago
    Events in Chicago · 6 guests

    29ft Sea Ray Sundancer Captained Boat In Chicago

    5.0
    Superowner
    $200/hour
    Rent this 42ft Regal Commodore Express Cruiser In Chicago
    Powerboats in Chicago · 13 guests

    Rent this 42ft Regal Commodore Express Cruiser In Chicago

    5.0
    Superowner
    Best of 2026
    $225+/hour
    Maxum 44ft Motor Yacht "My Kinda Party"
    Powerboats in Chicago · 13 guests

    Maxum 44ft Motor Yacht "My Kinda Party"

    4.9
    Superowner
    Best of 2026
    $260+/hour
    25ft Yamaha 252SE Jet Boat Charter in Chicago - Playpen Adventure
    Powerboats in Chicago · 10 guests

    25ft Yamaha 252SE Jet Boat Charter in Chicago - Playpen Adventure

    5.0
    $245/hour
    Double Decker 50ft Sea Ray Flybridge Yacht
    Events in Chicago · 13 guests

    Double Decker 50ft Sea Ray Flybridge Yacht

    5.0
    Superowner
    Best of 2026
    $300+/hour
    40ft Formula 370 Sun Sport Motor Yacht Charter Chicago Playpen Ready
    Events in Chicago · 12 guests

    40ft Formula 370 Sun Sport Motor Yacht Charter Chicago Playpen Ready

    5.0
    $300/hour
    24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!
    Powerboats in Chicago · 24 guests

    24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!

    5.0
    Superowner
    Best of 2026
    $800/hour
    Affordable Private Boat Rental for 12 on Lake Michigan/Playpen-39' Sea Ray Yacht
    Events in Chicago · 12 guests

    Affordable Private Boat Rental for 12 on Lake Michigan/Playpen-39' Sea Ray Yacht

    5.0
    $300/hour
    Limited Availability
    2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

    4.7
    $400/hour
    Limited Availability
    'Genius' 40ft Sea Ray Sundancer Captained Charter With All Amenities In Chicago!
    Events in Chicago · 13 guests

    'Genius' 40ft Sea Ray Sundancer Captained Charter With All Amenities In Chicago!

    5.0
    Superowner
    $275/hour
    Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago
    Events in Chicago · 13 guests

    Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago

    5.0
    Superowner
    Best of 2026
    $225+/hour
    Limited Availability
    Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago
    Sailing in Chicago · 6 guests

    Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

    5.0
    $200/hour
    Limited Availability
    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion
    Events in Chicago · 12 guests

    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

    5.0
    $250/hour
    42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!
    Events in Chicago · 12 guests

    42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!

    5.0
    $350/hour
    24 Guests Captained Party & Event Boat in Chicago with Bathroom & Aqua mat
    Powerboats in Chicago · 24 guests

    24 Guests Captained Party & Event Boat in Chicago with Bathroom & Aqua mat

    5.0
    Superowner
    Best of 2026
    $800/hour
    Limited Availability
    35' Maxum Motor Yacht At Burnham Harbor, Captain/Fuel Included
    Events in Chicago · 7 guests

    35' Maxum Motor Yacht At Burnham Harbor, Captain/Fuel Included

    5.0
    $275/hour
    High Demand
    27ft Chris Craft Motor Yacht With Water Toys plus Jet Ski Available in Chicago!
    Events in Chicago · 6 guests

    27ft Chris Craft Motor Yacht With Water Toys plus Jet Ski Available in Chicago!

    4.9
    Superowner
    $250/hour
    Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
    Sailing in Chicago · 10 guests

    Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

    5.0
    Superowner
    $250/hour
    Instant Book
    Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
    Powerboats in Chicago · 5 guests

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

    5.0
    Superowner
    $225/hour
    Limited Availability
    37' Silverton Spacious Party Yacht For Every Occasion In Chicago
    Events in Chicago · 12 guests

    37' Silverton Spacious Party Yacht For Every Occasion In Chicago

    5.0
    $225/hour
    Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
    Sailing in Chicago · 6 guests

    Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

    5.0
    $225/hour
    Set Sail on a Spacious 42' Silverton Express Cruiser Yacht
    Powerboats in Chicago · 13 guests

    Set Sail on a Spacious 42' Silverton Express Cruiser Yacht

    5.0
    $275/hour
    Limited Availability
    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!
    Events in Chicago · 13 guests

    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

    5.0
    Superowner
    $350/hour
    20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!
    Powerboats in Chicago · 20 guests

    20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

    5.0
    Superowner
    Best of 2026
    $700/hour

    Top Destinations Nearby

    Tours Reviews in Illinois

    1. KS

      Kailey

      20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

      We booked with Troy for an outing of 20 people and everyone had such a great time! Communication was very easy prior to the trip, having a captain included was huge, they have tables set up for games and food, a speaker system, floaties for the water, and the crew was very helpful! The views were also amazing! Would definitely recommend and would do again

    2. Cindy

      Cindy

      Maxum 44ft Motor Yacht "My Kinda Party"

      Had an amazing birthday weekend with my friends for my birthday, Captin Drake was great and I would definitely book again! Thank you for an amazing experience.

    3. DC

      Douglas

      Double Decker 50ft Sea Ray Flybridge Yacht

      Had a great time on the Chicago River and lake! Boat is a great value and lots of space to relax and enjoy the views.

    4. CG

      Cristobal

      Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

      Doug was great. Very helpful and informative. Would book again.

    5. KD

      Kareem

      2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

      Nilufar made the booking process so easy and we had no issues from start to finish!

    6. EE

      Emma

      24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!

      Such clear communication and made sure we had the best time!!

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