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    Lake Michigan, US Boat Rentals & Yacht Charters

    4.9
    (6,370 Reviews)

    Page 6 of 15 • 352 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    High Demand
    31ft Sea Ray 310 Sedan Bridge Motor Yacht Private Full Day Charter - Chicago, IL
    Events in Chicago · 12 guests

    31ft Sea Ray 310 Sedan Bridge Motor Yacht Private Full Day Charter - Chicago, IL

    5.0
    $300/hour
    Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer
    Powerboats in Chicago · 6 guests

    Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

    5.0
    $235+/hour
    Premium Sea-Doo Jet Ski Rental – Explore Chicago from the Water
    Water Sports in Chicago · 2 guests

    Premium Sea-Doo Jet Ski Rental – Explore Chicago from the Water

    New
    $150/hour
    Limited Availability
    Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat
    Powerboats in Chicago · 12 guests

    Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat

    New
    $325/hour
    High Demand
    Luxury Pontoon Boat Ride Along the Milwaukee River
    Powerboats in Milwaukee · 10 guests

    Luxury Pontoon Boat Ride Along the Milwaukee River

    5.0
    $150/hour
    Limited Availability
    Captained Charter on 60ft Sea Ray Luxury Yacht in Chicago with Captain Sam
    Events in Chicago · 20 guests

    Captained Charter on 60ft Sea Ray Luxury Yacht in Chicago with Captain Sam

    4.8
    $1,500/hour
    Limited Availability
    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!
    Events in Chicago · 12 guests

    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

    5.0
    Superowner
    Best of 2026
    $220/hour
    Instant Book
    Limited Availability
    13 Person 26ft Chaparral Powerboat on Lake Michigan with a Bathroom!
    Powerboats in Milwaukee · 13 guests

    13 Person 26ft Chaparral Powerboat on Lake Michigan with a Bathroom!

    5.0
    $110+/hour
    Cobalt 28' Bowrider for rent in New Buffalo (Captain Included!)
    Powerboats in New Buffalo · 6 guests

    Cobalt 28' Bowrider for rent in New Buffalo (Captain Included!)

    5.0
    $225/hour
    Limited Availability
    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago
    Events in Chicago · 13 guests

    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago

    4.9
    $400/hour
    Limited Availability
    Chicago looks better from the deck of 45' Rinker Motor Yacht
    Events in Chicago · 12 guests

    Chicago looks better from the deck of 45' Rinker Motor Yacht

    New
    $350/hour
    Limited Availability
    FourWinns Luxury Speed Boat available for Events, Date Nights and Family Outings
    Powerboats in Milwaukee · 6 guests

    FourWinns Luxury Speed Boat available for Events, Date Nights and Family Outings

    5.0
    Superowner
    $150/hour
    Sea Doo Spark iBR Jetski for Rent
    Water Sports in Traverse City · 6 guests

    Sea Doo Spark iBR Jetski for Rent

    New
    $149/hour
    Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht
    Events in Chicago · 6 guests

    Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht

    5.0
    $375/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
    28ft Wellcraft Suncruiser 288 Yacht for City Scape or Fishing Expo in Chicago
    Powerboats in Chicago · 6 guests

    28ft Wellcraft Suncruiser 288 Yacht for City Scape or Fishing Expo in Chicago

    1.0
    $250+/hour
    Pontoon Rental in Fennville $1900 six Days 3 days mid-week 1400$ NO DAILYS
    Powerboats in Michigan · 13 guests

    Pontoon Rental in Fennville $1900 six Days 3 days mid-week 1400$ NO DAILYS

    5.0
    $272+/day
    High Demand
    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
    Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests
    Events in Chicago · 7 guests

    Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests

    5.0
    Superowner
    $500+/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
    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
    Instant Book
    Limited Availability
    Luxury 45’ Catamaran in Chicago | Up to 40 Guests
    Events in Chicago · 40 guests

    Luxury 45’ Catamaran in Chicago | Up to 40 Guests

    5.0
    Superowner
    Best of 2026
    $950/hour
    Instant Book
    33ft Bayliner Powerboat Charter in Chicago for 10 Guests
    Events in Chicago · 10 guests

    33ft Bayliner Powerboat Charter in Chicago for 10 Guests

    4.6
    $300/hour

    Top Destinations Nearby

    Lake Michigan Reviews

    1. NM

      Nancy

      Luxury 45’ Catamaran in Chicago | Up to 40 Guests

      We had such a great time on this boat. We were all surprised with how amazing it was. There was so much space we were shocked. We brought so much food and so many coolers on top of 17 people and there was still room. We all were able to sit and talk to one another. Already planning on booking this rental again. The crew was amazing and so helpful.

    2. EL

      Elizabeth

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

      Loved the boat, the captain was wonderful, communication was the best. Everything was perfect we can’t thank you enough for 4 fabulous hours in the playpen for my weekend celebration. Thx you for making it so easy. We will book this boat and captain again!

    3. LR

      Luis

      Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

      We would strongly recommend hiring Diego. The bote is perfect, he is a very nice person and tries his best to make you live a fantastic experience. If you are in Chicago, do not hesitate, contact him immediately.

    4. BD

      Brittany

      Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

      We had a great time on our trip with Diego! He had a great route planned for us to see the river and stop by the playpen and see the city from the lake. He was a great communicator before the trip. He let us know all the details we needed ahead of time to have a smooth trip. We all had a wonderful time!! Highly recommend!!

    5. JB

      Janell

      Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

      It was great time with Diego, showed us various sites and attractions throughout the Chicago area. Definitely would book with him again.

    6. MS

      Mayukh

      Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

      Boat is even more spacious in pictures. Our captain Lemzar was great! Beautiful way to kick of our boy’s bachelor weekend

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