GetMyBoat Logo

    Browse Boat Rentals in Chicago, IL.

    Average of 2,201 reviews in this area.
    1 - 18 of 119 listings
    37' Luxury Sailboat with Captain
    hour$300
    Super Owner6 guests

    37' Luxury Sailboat with Captain

    33' Captained Charters in Chicago aboard SeaVibes!
    hour$270
    Super Owner6 guests

    33' Captained Charters in Chicago aboard SeaVibes!

    FunTime 2 Chicago on Party Boats
    hour$823
    Super Owner20 guests

    FunTime 2 Chicago on Party Boats

    Trident 38' Pontoon Party Boat for Charter in Chicago
    hour$700
    Super Owner20 guests

    Trident 38' Pontoon Party Boat for Charter in Chicago

    Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
    hour$200
    Super Owner5 guests

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

    Double decker flybridge yacht with great reviews!
    hour$325
    Super Owner12 guests

    Double decker flybridge yacht with great reviews!

    HUGE affordable boat! Best rates for your group of up to 12!
    hour$220
    Super Owner12 guests

    HUGE affordable boat! Best rates for your group of up to 12!

    40ft Got a Life Formula 40 PC Motor Yacht Rental in Chicago, Illinois
    hour$450
    Super Owner12 guests

    40ft Got a Life Formula 40 PC Motor Yacht Rental in Chicago, Illinois

    50' Multi-level Luxury Yacht with Party up to 12
    hour$500
    Super Owner12 guests

    50' Multi-level Luxury Yacht with Party up to 12

    31' Captained Yacht, Fun in Chicago Aboard
    hour$275
    Super Owner6 guests

    31' Captained Yacht, Fun in Chicago Aboard

    Beautiful Luxury Cruiser 40' Sea Ray Sundancer for Charter in Chicago
    hour$238
    Super Owner12 guests

    Beautiful Luxury Cruiser 40' Sea Ray Sundancer for Charter in Chicago

    44' Sea Ray Sundancer Luxury Motor Yacht Rental
    hour$499
    Super Owner12 guests

    44' Sea Ray Sundancer Luxury Motor Yacht Rental

    44' Luxury Yacht Rental/Party Boat in Chicago, Illinois
    hour$499
    Super Owner12 guests

    44' Luxury Yacht Rental/Party Boat in Chicago, Illinois

    44' Luxury Sundancer Yacht Rental! Includes Floating Island!
    hour$499
    Super Owner12 guests

    44' Luxury Sundancer Yacht Rental! Includes Floating Island!

    Amazing Party Cruising Trips on 34 ft Cruiser in Chicago, Illinois
    hour$434
    Super Owner16 guests

    Amazing Party Cruising Trips on 34 ft Cruiser in Chicago, Illinois

    100+ results

    Boating Guide - Chicago

    How to rent a boat on GetMyBoat

    1. Search by location

    Tell us where you want to pick up or where you want to go boating

    2. Filter search results

    Sort by boat type, price, and group size

    3. Submit a booking inquiry

    Learn more about your favorite boat and the best local destinations

    4. Pay for the rental

    The owner will send you a custom quote that can be booked with a credit card

    Find the perfect boat rental in Chicago. Simple, easy, and secure.

    When you’re not walking around the busy city, attending an outdoor festival, or running along the path, checking out boat rentals in Chicago is a great way to experience Chicago. Once you are on a boat, you will see beautiful views of the skyline and downtown, and you can really disconnect from the hustle and bustle. Although famous for being the Windy City, boat lovers know that this epithet rarely does justice to Chicago. You have endless options for finding boat rentals, yacht charters, and fishing charters in Chicago. You can choose from powerboats, cruises, party pontoon boats, sailing charters, motor yachts, Jet Ski Rentals, and more. The city’s typically continental type of climate includes hot summers and pleasant spring and fall seasons which adds its own charm to explore the waterways. The temperate weather and relaxed waters make the time of year ideal for your travel plans.

    Although the seasons are open for boating all year round in Illinois, the best time of year to enjoy the water and find a boat rental in Chicago is during the summer season. Illinois itself as a great state for boating and fishing enthusiasts. Most people don’t think of the Midwest when they think of beaches, but Chicago has some great areas for relaxing and enjoying the city’s beautiful summer weather.

    If you are looking to visit one of the most popular boating destinations in Chicago, then rent a boat to visit the Playpen. Charter a yacht and go out for a fun-filled day on the water, then walk over for some of the best nightlife in town. If you are on a romantic getaway in Chicago you might also like to check out these cool hot tub suites for a romantic place to stay.

    The city promises thousands of miles of shoreline and many beautiful lakes. Add to that the splendid view of Chicago’s skyline from the water and you have an experience that you wouldn’t want to miss. Events in the Chicago area take place all year round so finding activities to keep you busy will not be difficult. Check out this Chicago Travel Guide by TourScanner for more ideas on things to do during your visit. During the summer, all harbors open for most of the season. Try booking a trip during the Chicago Air and Water show and watch the event festivities from the water. Simply cruise towards Navy Pier for a view that you will remember for life. Take a day or a night cruise in one of the powerboats and don’t forget to watch the fireworks near Navy Pier on Wednesday and Saturday nights. In fact, if watching the show is on your bucket list, it is best to take a fireworks cruise and enjoy it from the water. Columbia Beach is a hidden gem with great views without the crowds. The 31st Street Beach in the South Side has a nearby park and there’s easy access for small boats.

    There are many great boating destinations in and around Chicago including Winthrop Harbor, Hammond, Waukegan, Milwaukee, Kenosha, and Winnetka. If trekking is your thing, you may even explore the Fox and Crystal Lakes for a nice boating experience.

    Boating Events in Chicago

    Whether you are looking for a boat rental for a bachelorette party in Chicago or a birthday party, there are some very popular days to rent a boat and head out on the water. If you are looking to rent a boat for the Chicago Air and Water Show, we suggest you book far in advance of August because these dates book up months in advance.

    Need a captained yacht charter for the Chicago Boat Scene Party? We have you covered. GetMyBoat has all sorts of captained charters so that you can celebrate the 16-year tradition that is hosted in the Playpen. It is advised to book a rental early as this is the second most popular day to hit the waters.

    Marinas Around Chicago

    Chicago is comprised of over 24 marinas that are able to hold thousands of boats in their combined slips. While marinas are spread out across the town, a few of the most popular marinas in Chicago are Burnham Harbor, DuSable Harbor, Diversey Harbor Lagoon, Belmont Harbor, River City Marina, Monroe Harbor, and 31st Street Harbor. These harbors give access to some of Chicago’s best boating hot spots and are close by hotels and plenty of city life.

    About Chicago

    As the third-largest city in the U.S., Chicago is a vibrant urban destination with a lot to do and see. Its picturesque location on Lake Michigan, its stunning architecture, and its position as a cultural leader make Chicago a popular tourist destination.

    The best time to visit and rent a boat in Chicago is in the summer months between June and August. Between these months you can expect the temperature to be around the high 50s to high 80s, depending on if there are any unforeseen heatwaves. Even though the temperatures will tend to be on the higher side, it is advised to bring layers while boating because it can get breezy and is also known to rain in August. The summer months in Chicago are also great for boating because of the long days with sunrise around 6 am and sunset around 8 pm.

    Once you’re docked, check out some of Chicago’s outdoor spaces on foot, including nearby parks, sculptures, and events. Cloud Gate, also known as The Bean, is one such sculpture, located in the middle of Millennium Park. The Bean makes for great vacation photos and there are thousands of photos tagged here on Instagram. Lincoln Park and Grant Park are also excellent spots to visit. If you are interested in Chicago’s unique events, check out their food, music, and dance festivals throughout the year. Lollapalooza, Chicago Dancing Festival, Chicago Jazz Festival, and the Food Truck Social are just a few of the many events held in the area.

    Try other top experiences in Chicago

    Chicago Pontoon Rentals

    Chicago Fishing Charters

    Chicago Sailboat Rentals

    Chicago Boat Rental FAQs

    How much does it cost to rent a boat on Lake Michigan?

    Renting a boat in Chicago starts at $100 an hour for a small powerboat and goes up to $800 an hour for a luxury motor yacht.

    How much is it to rent a yacht in Chicago?

    A smaller size motor yacht rental will cost around $250 an hour, while a larger yacht can cost up to $700 an hour. When getting a quote, inquire if the captain’s fee and gas are included in the price.

    What are the best places to go boating in Chicago?

    While there are many options while boating in Chicago here is a list of the most visited boating destinations and tours in Chicago.

    • Navy Pier
    • Playpen
    • Chicago Architecture Tour
    • Cruise The River
    • Shoreline Tour

    When is the boating season in Chicago?

    While boating season in Chicago can vary depending on the weather, it usually starts at the beginning of May and can extend through to October.

    What is the Playpen in Chicago?

    The Playpen is one of the most popular boating destinations in Chicago. It’s a protected area in front of Lake Shore Drive created by a breakwall in front of the water filtration plant. It’s the perfect destination for swimming, boat parties, and floating. Boaters stop here and tie-up with other boats for an on-the-water social affair. In fact, the Playpen hosts the largest annual boat party in all of Chicago, dubbed the Chicago Scene Boat Party.

    What is the Chicago Scene Boat Party

    The Chicago Scene Boat Party is an annual event held in the Playpen where hundreds of boats tie up for what is now the largest boat party on Lake Michigan. This event is usually held the last weekend of July, but boat rental reservations fill up months in advance. The Chicago Scene Boat Party was started in 2000 by Ted Widen, the publisher of the luxury lifestyle mag Chicago Scene.

    Does the boat rental include a captain?

    Boats listed on GetMyBoat offer boat rentals with or without a captain in Chicago. You can always communicate with the boat owner through GetMyBoat before confirming your booking to ensure your captain and crew needs are met.

    Why choose GetMyBoat over Airbnb for boat rentals in Chicago?

    While Airbnb has a few boats or yachts that you can sleep in overnight at the marina, they do not allow you to go out on the boat. GetMyBoat specializes in top-quality boat rentals and yacht charters in Chicago that allow you to leave the dock and experience the water. Don't just sleep on the boat, explore with the boat.

    GetMyBoat customer reviews for boat rentals in Chicago.

    1. GM
      Gerald
      37' Luxury Sailboat with Captain

      We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.

    2. Bailey
      Bailey
      37' Luxury Sailboat with Captain

      We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with taking the photos and positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.

    3. Dyna
      Dyna
      37' Luxury Sailboat with Captain

      I rented the boat to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner! The boat is very spacious! We had 6 people and Greg was our captain but still had so much space to move around the boat! Greg is very laid back and easy to talk to. We brought food, alcohol and birthday cupcakes on board the boat. There’s a mini fridge to keep stuff cold. There was an aux cable so I was able to play music. There’s also a bathroom on the boat. Overall, I’d definitely recommend Greg and Cait!

    4. SM
      Scott
      37' Luxury Sailboat with Captain

      Greg was a patient, sure captain who did a great job showing us around the lake. He knew weather was going to roll in before it actually did and made sure we got in our fun and got us to the dock right before a storm rolled through and was kind enough to allow us to stay aboard until it was done. Great job

    5. BB
      Brandon
      37' Luxury Sailboat with Captain

      It was an amazing relaxing time , fully stop. Nothing but good conversation with my party and the captain and his first mate. Everything was clean and they were great host. Even help ppl in my party that got motion sickness. They are clearly experts at sea and hosting. Book this boat and make memory.

    6. Kate
      Kate
      37' Luxury Sailboat with Captain

      We had a fabulous time on the Dragonfly. Greg and Cait’s experience is top notch and one of a kind. Cait was busy so we were just with Greg and we cannot say enough about the day. The boat was so nice, he was a clear expert and great company. Clean bathroom, snacks and drinks, a fridge, lots of room - Thank you!

    GetMyBoat has 119 listings for boating experiences in Chicago with 2,201 reviews.

    Search Chicago