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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,897 Reviews)

    Page 8 of 12 • 285 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    40ft Carver Mariner Motor Yacht Charter in Chicago
    Events in Chicago · 13 guests

    40ft Carver Mariner Motor Yacht Charter in Chicago

    New
    $745/hour
    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina
    Events in Chicago · 36 guests

    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

    5.0
    $793/hour
    Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago
    Events in Chicago · 12 guests

    Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago

    5.0
    Superowner
    Best of 2026
    $375+/hour
    41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago
    Events in Chicago · 12 guests

    41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago

    5.0
    Superowner
    Best of 2026
    $375+/hour
    40' Cruisers Yachts "Bad Boys II" for rent in Chicago
    Events in Chicago · 13 guests

    40' Cruisers Yachts "Bad Boys II" for rent in Chicago

    New
    $818/hour
    High Demand
    52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!
    Events in Chicago · 13 guests

    52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

    5.0
    $225+/hour
    Limited Availability
    38ft Lagoon Catamaran Sailing Lessons in Chicago
    Tours in Chicago · 6 guests

    38ft Lagoon Catamaran Sailing Lessons in Chicago

    New
    $350+/hour
    Limited Availability
    42ft Sea Ray Motor Yacht in Chicago, Burnham Harbor (Up to 12 guests)
    Events in Chicago · 12 guests

    42ft Sea Ray Motor Yacht in Chicago, Burnham Harbor (Up to 12 guests)

    New
    $300/hour
    High Demand
    Sea Ray 460 Sundancer Yacht - Enjoy the summer Chicago scene!
    Events in Chicago · 12 guests

    Sea Ray 460 Sundancer Yacht - Enjoy the summer Chicago scene!

    New
    $400/hour
    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL
    Events in Chicago · 13 guests

    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL

    New
    $1,089/hour
    Limited Availability
    Stunning 51' Sea Ray Sundancer with USCG Captain in Chicago
    Events in Chicago · 12 guests

    Stunning 51' Sea Ray Sundancer with USCG Captain in Chicago

    New
    Superowner
    Best of 2026
    $450/hour
    Limited Availability
    49 Passengers 57' Power Catamaran - Perfect For Events in Chicago
    Events in Chicago · 49 guests

    49 Passengers 57' Power Catamaran - Perfect For Events in Chicago

    5.0
    Superowner
    $1,000/hour
    Limited Availability
    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
    Sailing in Chicago · 12 guests

    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

    4.8
    $245/hour
    Instant Book
    Italian Luxury Azimut 63ft Yacht Charter for 12 Guests in Chicago
    Events in Chicago · 12 guests

    Italian Luxury Azimut 63ft Yacht Charter for 12 Guests in Chicago

    New
    $800/hour
    Limited Availability
    Private Boat Charter - Sea Ray 390 Sundancer In Chicago
    Events in Chicago · 12 guests

    Private Boat Charter - Sea Ray 390 Sundancer In Chicago

    5.0
    $350/hour
    Premium 55' Sea Ray Yacht Charter - Seakeeper Stability, Chicago Lake Michigan
    Events in Chicago · 12 guests

    Premium 55' Sea Ray Yacht Charter - Seakeeper Stability, Chicago Lake Michigan

    New
    $1,404/hour
    Luxury Multi-Level Carver 38' Yacht with Premium Sound & Spacious Layout
    Events in Chicago · 12 guests

    Luxury Multi-Level Carver 38' Yacht with Premium Sound & Spacious Layout

    5.0
    $225/hour
    Limited Availability
    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests
    Events in Chicago · 12 guests

    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests

    4.9
    $300/hour
    Limited Availability
    New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain
    Powerboats in Chicago · 13 guests

    New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain

    5.0
    Superowner
    $275/hour
    High Demand
    62' Azimut Italian Luxury Yacht for Rent in Chicago, Illinois for 13 Guests
    Events in Chicago · 13 guests

    62' Azimut Italian Luxury Yacht for Rent in Chicago, Illinois for 13 Guests

    3.0
    $1,000/hour
    Limited Availability
    Experience Chicago by the water - Rent this 38' Traident Party Pontoon
    Powerboats in Chicago · 20 guests

    Experience Chicago by the water - Rent this 38' Traident Party Pontoon

    5.0
    Superowner
    Best of 2026
    $680/hour
    Limited Availability
    39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
    Events in Chicago · 12 guests

    39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

    5.0
    Superowner
    Best of 2026
    $350+/hour
    Limited Availability
    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests
    Events in Chicago · 12 guests

    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests

    New
    Superowner
    Best of 2026
    $160+/hour
    Instant Book
    Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style
    Events in Chicago · 13 guests

    Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style

    5.0
    $950/hour

    Top Destinations Nearby

    Chicago Reviews

    1. CH

      Carlisha

      Private Boat Charter - Sea Ray 390 Sundancer In Chicago

      Everything was five stars from the time we stepped on the dock to the time we returned. We had an amazing time! Thank you sooooo much. Until next time!

    2. SB

      Sarah

      52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

      Great experience! Communicative host, boat as described, definitely a great value for our money. Would recommend!

    3. Olivia

      Olivia

      Chicago: Classic 63' Chris Craft Constellation Luxury Yacht w/ Exquisite Style

      Great coordination ahead of time, super convenient to board from the river, beautifully kept vintage boat!

    4. JD

      Jorge

      No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

      Captain Dennis and Kate were great hosts. Everything was perfect

    5. EW

      Evan

      No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

      Incredible time!! Large boat for a large group of people and so fun!!

    6. RC

      Rachel

      Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago

      It was great! We ended up having a little later departure and they extended our arrival by the amount of time we missed out on from the departure. Really appreciate all the communication and help from James and his crew! Thank you so much, it was so fun!

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