It may not be by the ocean, but Chicago is a waterfront city.
With the scenic Lake Michigan to the East and the landmark Chicago River flowing through downtown, it’s not uncommon for residents to take to the water and experience a bit of the sea during the summer months. After all, the Playpen—where dozens of boats anchor to experience the sun—is a Chicago Summer staple.
You don't have to buy a boat to get in on this action. There are plenty of companies at the ready to rent you a boat, whether it be a pontoon, electric, retro or an all-out luxury yacht. Check out our picks for the top rentals in the Windy City and get out there.
See also: The 13 Best Rooftop Patios To Eat And Drink Outside In Chicago
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3600 N. Recreation Dr. / Website
This service has earned a five-star reputation for its yacht and speed boat rentals. One of several locations, this chain offers plenty of captains to guide you throughout your yacht experience, so you can have fun on the water without fear of inexperience. Customers have raved about “Captain Jack.” With a name like that, you’ve got to trust these sailing chops! Chicago Motor Yacht also offers 30-foot speed boats for an exhilarating day out on Lake Michigan.
1438 W. Cortland St. / Website
Looking for more of a cruise than a swim? North Shore has just the boats for you. While its lake availability does depend on weather conditions, the company promises a relaxing cruise along the scenic Chicago River, prioritizing your private party above all else. Reviews rave about the customer service with parties, saying the crew works well to communicate with outside services such as catering and movement to bring your party to the waterfront, as well as prioritize safety. Take a load off this summer, and cruise like Nelly.
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4250 N. Marine Dr., Apt. 1709 / Website
With a fleet of three yachts, this party boat experience promises its namesake and much much more. Cruising along Lake Michigan and offering vistas of Chicago landmarks like Adler Planetarium and Buckingham Fountain, this is the perfect place for getting away or hosting memorable parties. Fun in the Sun also offers some unique options, including your own charter for an additional fee and nighttime cruises to see semi-regular firework displays.
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1177 N. Elston Ave. / Website
Yachts not your thing? Maybe you want something more casual, like a pontoon boat. Chicago Boat Rental is just the place for that, offering 18 and 22-foot pontoons to cruise along the Chicago River, fitting six and 10 passengers, respectively. With bluetooth speakers, BYOB and catering options, and the ability to captain your own vessel along the river, this is the perfect way to sneak in a day of summer fun. Plus, if yachts do appeal to you, they offer a charter on Lake Michigan. The staff has been raved about online, and, like others, they offer a fireworks cruise with the best views in the city.
See also: Ikram's It List For Summer Footwear
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400 Belmont Harbor Dr. / Website
Yachts and pontoon boats are great, but if you really want to get back to basics and feel the wind on your skin, this is your chance. Offering charter cruises with a variety of experiences from fireworks to night sailing, swimming and sunning, these captained vessels are a great way to enjoy a day in the sun with a party group or a romantic getaway. Sunset sailing with a surprise proposal with the skyline behind you? Can’t get more Insta-worthy than that.
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300 N. State St. / Website
One of the most highly-reviewed options online, this simple-to-use service promises a great scene around Chicago. Electric, bus-style boats are perfect for simple groups looking to see the city from its famous river, while exercise buffs may go for the first-ever cycleboat. There are also retro boats fitted from the 1950s and '60s for those trying to bring a bit of Venice to their river ride, and like many others, Chicago Electric Boat Company does offer yacht services for those looking to get into the Playpen; cocktail and chef service optional.
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465 North Park / Website
Boasting itself as “Chicago’s #1 Yacht Rental,” this luxury option offers some of the most impressive options in its catalog, including boats up to 50 feet long. Looking for something simple? This company offers 30-foot speedboats at about $225 an hour, perfect for a nice, cruising experience. With affordable prices and amenities to bring your own food and drinks, this is one of the primary rental options for a great day on the water.
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200 N. Breakwater Access / Website
With 31 years of experience and the most reviews of any service online, this is one of the most reliable options for a true luxury experience. Featuring two yachts—fittingly named the Anita Dee I and the Anita Dee II—the service promises pure control over any large event the vessel can carry. Weddings, corporate retreats, or even just a large shindig for you and 400 of your closest friends—it all gets the green light. The service also offers catering, bar service and amenities for any such event. Not exactly perfect for a weekend getaway, but for a private event unlike any other, the Lake beckons for Anita Dee.
Photography by: Scott Greer/Unsplash
