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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,719 Reviews)

    Page 7 of 12 • 282 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    36' Wellcraft Grand Sport Yacht for Intimate Gatherings and Events in Chicago
    Events in Chicago · 12 guests

    36' Wellcraft Grand Sport Yacht for Intimate Gatherings and Events in Chicago

    5.0
    $250/hour
    Limited Availability
    Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations
    Powerboats in Chicago · 12 guests

    Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

    5.0
    Superowner
    Best of 2026
    $190/hour
    Instant Book
    32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests
    Events in Chicago · 6 guests

    32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests

    5.0
    $300/hour
    Learn Kiteboarding in Chicago with Professional Kiteboard Instructor
    Adventures in Chicago · 1 guest

    Learn Kiteboarding in Chicago with Professional Kiteboard Instructor

    5.0
    $185/hour
    Limited Availability
    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
    $250/hour
    Limited Availability
    44' Luxury Sea Ray Express Yacht Rental/Party Boat with Captain in Chicago
    Events in Chicago · 13 guests

    44' Luxury Sea Ray Express Yacht Rental/Party Boat with Captain in Chicago

    4.9
    $349/hour
    Limited Availability
    55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand
    Events in Chicago · 12 guests

    55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

    5.0
    $375+/hour
    Limited Availability
    Private Charter 38' Party Pontoon for up to 20 Guests in Chicago
    Powerboats in Chicago · 20 guests

    Private Charter 38' Party Pontoon for up to 20 Guests in Chicago

    5.0
    Superowner
    Best of 2026
    $700/hour
    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
    Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!
    Events in Chicago · 120 guests

    Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!

    5.0
    $1,500/hour
    Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Yacht
    Events in Chicago · 10 guests

    Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Yacht

    5.0
    $275/hour
    Limited Availability
    SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests
    Events in Chicago · 12 guests

    SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests

    5.0
    $200/hour
    See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht
    Events in Chicago · 13 guests

    See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht

    5.0
    Superowner
    Best of 2026
    $300/hour
    Instant Book
    Limited Availability
    50' Multi-level Sea Ray Luxury Yacht with Party up to 12 in Chicago
    Events in Chicago · 12 guests

    50' Multi-level Sea Ray Luxury Yacht with Party up to 12 in Chicago

    5.0
    Superowner
    Best of 2026
    $350/hour
    Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago
    Powerboats in Chicago · 8 guests

    Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago

    New
    $248/hour
    One of the most unique charter yacht ever to arrive in Chicago - 46' Rio Coupe
    Events in Chicago · 12 guests

    One of the most unique charter yacht ever to arrive in Chicago - 46' Rio Coupe

    New
    $400/hour
    Limited Availability
    Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!
    Events in Chicago · 12 guests

    Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!

    4.9
    Superowner
    Best of 2026
    $400/hour
    Instant Book
    50ft Searay 400 Yacht - Lake Michigan Chicago - Up to 13 Guests
    Events in Chicago · 13 guests

    50ft Searay 400 Yacht - Lake Michigan Chicago - Up to 13 Guests

    New
    $300/hour
    34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!
    Events in Chicago · 12 guests

    34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!

    New
    $300/hour
    Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago
    Events in Chicago · 12 guests

    Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago

    5.0
    $325/hour
    Take in Breathtaking Chicago Skyline Views from Spacious 32' Chaparral Yacht
    Events in Chicago · 12 guests

    Take in Breathtaking Chicago Skyline Views from Spacious 32' Chaparral Yacht

    New
    $450/hour
    Limited Availability
    35’ Sea Ray Yacht, Playpen, River Cruises up to 13 people Captain included!
    Events in Chicago · 11 guests

    35’ Sea Ray Yacht, Playpen, River Cruises up to 13 people Captain included!

    5.0
    $300/hour
    Tiki Themed 24' Key West Boat with Captain & Beverage Package | Chicago
    Powerboats in Chicago · 6 guests

    Tiki Themed 24' Key West Boat with Captain & Beverage Package | Chicago

    5.0
    $200/hour
    Limited Availability
    45ft Sea Ray Sundancer Motor Yacht Pure Comfort in Chicago!
    Events in Chicago · 10 guests

    45ft Sea Ray Sundancer Motor Yacht Pure Comfort in Chicago!

    5.0
    $300/hour

    Top Destinations Nearby

    Chicago Reviews

    1. SJ

      Sam

      See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht

      Kevin was professional, friendly, and - most importantly - fun. He and captain William were pro navigators and never did anything risky. They're solid guys with a great boat and I wouldn't hesitate to rent from these guys again.

    2. AG

      Alyssa

      Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

      Highly recommend! So much fun

    3. ct

      chelsea

      Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

      Kevin and Alex were amazing! We arrived a little early and Kevin assisted us with all of our baggage. Check in and safety briefing was quick yet informative. Captain Alex was amazing and provided us with the perfect combination of boating down the river and ending our charter in the playpen for a quick dip! I can’t recommend Kevin and his team enough! It was an amazing day

    4. KM

      Katiana

      Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

      The crew was so communicative leading up to the date. The boat was amazing! So much space and so clean. I highly recommend this team. Captain Evan was all about keeping us safe, but also ensuring we got the best time in the water. I’d book again! This is gonna become a yearly tradition.

    5. CM

      Connor

      Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

      Fantastic day on the water! The entire process was so smooth and easy to get ready for the rental. Finding a captain was easy and Hayden was phenomenal! He was very clear with what we needed and safety in/around the boat. Will definitely be booking again in the future

    6. CS

      Carol

      Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations

      We had such a great time! Our captain, Zack, was great and super friendly! Communication with the Captain and owner was super simple and always met with a quick response. Our group is already talking about the next time we can go out! Such a great find!

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