Chicago is a vibrant urban destination with a lot to do and see. Its position on massive Lake Michigan gives the feeling of a coastal city, surrounded by water and gorgeous views. It’s an excellent destination for tourists from all over, who want to not only experience the city life but also want to enjoy some time out on the water, cruising on the lake to relax.

Want more ideas for your trip to Chicago? Check out this article by Tour Scanner on 77 Fun & Unusual Things to do in Chicago! There's so much to do on land too!

The best time to visit and rent a boat in Chicago is in the summer months. From late May through August, you’ll have the best chance of sunshine and warm temperatures. You’ll have extended hours of daylight, too, perfect for making the most of a half-day boat rental or even a full-day excursion on the river and Lake Michigan.

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All About Chicago Boat Rentals & Boat Tours

When you’re not walking around checking out Millenium Park and Cloudgate (the Bean) or exploring Chinatown, checking out boat rentals in Chicago is a great activity choice. Once you are on a boat, you will see beautiful views of the skyline and downtown, and you can disconnect from the hustle and bustle.

Renting a boat in Chicago is an excellent choice for hosting events. Bachelor and bachelorette parties, weddings, corporate cruises, and family gatherings are extra special when enjoyed on a yacht charter. Cruise the river for a history tour on the water, or experience a full-blown boat party onboard at hot spots like the Playpen. Once you’ve picked your dates to visit Chicago, be sure to start looking to book a boat rental, as reservations fill up in advance, especially in the summer months.

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Types of Boats to Rent in Chicago

No matter your budget or the size of your group, you can find a boating experience in Chicago to match it. If you don't have any boating experience, don't worry. There are lots of boat rentals in Chicago that come with a captain included, so you can relax and enjoy your boat day without having to navigate Lake Michigan or the river.

Party Pontoon Rentals in Chicago

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Starting at $800/hour for a 20-person party boat, party pontoons in Chicago are an excellent choice for bachelor and bachelorette parties and other large group celebrations. Tie up a floaty and sunbathe next to your boat, enjoy drinks onboard, and see the skyline of Chicago while making memories with your closest friends or family. Don’t forget to sort out a killer playlist before you board - party pontoons come equipped with Bluetooth speakers to hook up to your tunes.

Sailing Tours in Chicago

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It’s not called the Windy City for no reason! Although not the reason for the origin of the name, the lakefront of Chicago is breezy, making it a fantastic destination for sailboat rentals and sailing tours. Sail on a yacht for as little as $180/hour. Sailboat charters come with a skipper in many instances. A sunset sailing trip in Chicago is a romantic way to see the city. If you book on a Wednesday or Sunday in the summer, you’ll get a chance to see the fireworks at Navy Pier from your boat deck, a fantastic alternative to the hoards of crowds onshore.

Boat & Yacht Rentals in Chicago

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Want a little more speed than a sailboat? Boat and Yacht rentals in Chicago are the ultimate weekend activity for visitors and locals alike. If you don’t have boating experience or the correct licensing - no problem. Captained charters are available, and this way, no one in your group has to worry about driving the boat. Starting around $200/hour, you can get out on Lake Michigan or cruise up and down the river with a powerboat rental in Chicago. Customize your trip itinerary to include sunset cruises, fireworks viewings, meals, drinks, stops at beaches or the Playpen, and floaties to enjoy while out cruising.

Kayak Tours & Stand-up Paddleboard Rentals in Chicago

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For visitors to Chicago who prefer to maintain their fitness and get some exercise while exploring a new place, kayak rentals and kayak tours are the way to go. Kayak rentals in Chicago start around $25/hour, and you can book tours with a guide to take you paddling around the river or on the lake. It’s a fantastic option for seeing more of the city while getting in a great workout. Stand-up paddleboard rentals are also available in Chicago, which you can take out from the beaches for a fun activity to enjoy the sunshine.

Jet Ski Rentals in Chicago

For fun and excitement on the water in Chicago, rent a jet ski. Jet ski rentals start around $100/hour in Chicago, and they are the best way to enjoy a thrilling tour around Lake Michigan and the river. Zip through the waves and see the skyline at high speed, race your friends and fly around on a jet ski.

Boat Tours of the Chicago River

The Chicago River is a popular destination for boat tours and boating experiences. One of the top tours sought by visitors is an Architectural River Tour of Chicago. On a tour, you can pass by landmarks like the Willis (Sears) Tower, the Wrigley Building, and Navy Pier. The riverfront of Chicago is picturesque, and nothing beats cruising by it on a boat. You can also try kayak tours of the Chicago River.

Boating Destinations in Chicago

The Playpen

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. The Playpen hosts the largest annual boat party in all of Chicago, dubbed the Chicago Scene Boat Party.

Navy Pier

Navy Pier is an excellent stop on a sightseeing tour of Chicago. It’s the most visited attraction of the city, so arrive in style on your boat rental! Here you can dock to visit a waterfront restaurant right on the Pier. A few to choose from include: Riva Crabhouse, Tiny Tavern, or stop for a sweet treat at Frío Gelato. Navy Pier is an exceptional yacht stop and should be on a boat day itinerary for all visitors and locals in Chicago.


North Side Beaches of Chicago

Want to cruise to a beach while on your boat rental in Chicago? Head to the north side. You’ll get great views of the skyline from spots like Columbia Beach, Montrose Beach, North Avenue Beach, and Ohio Street Beach. Stop for a swim or a picnic on these beaches and admire the glimmering waters of Lake Michigan and the impressive downtown Chicago Skyline.

Boating Events & Boat Parties in Chicago

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 during 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.

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. Book a rental early as this is the second most popular day to hit the waters.

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Rent a boat in Chicago to Celebrate Lollapalooza or Jazz Festival

Chicago is home to many epic music festivals and celebrations, attracting visitors from all over the country and the world. When going to Chicago to enjoy one of these events, you must find other activities to enjoy in addition to the shows. Book a boat rental to pregame for Lollapalooza or to relax after. You can even make a boat your accommodation in Chicago if visiting for these events - overnight yacht rentals with cabins are available in Chicago.

Check out the Chicago Air & Water Show from a Boat Rental

The Chicago Air & Water Show takes place annually in August and is a massive event in the city. The best viewpoint to see the planes and events is from the water, and a boat charter is the best way to get out, away from the crowds, with an unblocked view of all the action. Want to book a boat to see the Chicago Air and Water Show? It’s advisable to book far in advance of August because these dates book up months before the show.

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A visit to Chicago is not complete without getting out on the water. No matter your budget, boating skills, or experience level, you can find the perfect boat rental with Getmyboat in Chicago. Search your options on the website or mobile app to see what’s available during your dates in Chicago.