Best Boat Rentals Near Chicago, IL
Labor Day Weekend Boat Rentals
Top Boat Rentals and Yacht Charters in Chicago, IL
$162+
Top boat rental reviews in Chicago, IL
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5/5 stars
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5/5 stars
The charter was amazing! Lovely boat with great space & both Captain Sam & Kadence were wonderful!
Leslie
Sep 2025 -
5/5 stars
Amazing experience! The captain was really nice and gave excellent customer service!
Ololade
Sep 2025 -
5/5 stars
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5/5 stars
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5/5 stars
Steph is absolutely amazing! Highly recommend! Thank you, again.
Roberta
Sep 2025 -
5/5 stars
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5/5 stars
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5/5 stars
Had such a great time on this boat and had tremendous service - will be booking again!
Tessa
Sep 2025 -
5/5 stars
Great communication from Robert & excellent boat! Will defintely book again, thanks!
Enrique
Sep 2025 -
5/5 stars
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5/5 stars
How to rent a boat in Chicago?
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Enter your desired location and date to explore our fleet of boat, Chicago, IL, United Statess.
Select a captain
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Set sail
Enjoy your day on the water with friends and family!
Chicago boating is unique to any other larger-scale city. The cityscape is hugged by the freshwater of the great Lake Michigan connecting it to three other US states. Even reachable by ocean-going vessels, Chicago’s boating scene is well-loved. Boaters enjoy a variety of boating activities on Lake Michigan, including yachting, kayaking, diving, kite surfing, and jet skiing.
What To Know
The lake is jam packed in the summer season as everyone in the city flocks to Lake Michigan. This is a consequence of the small window of opportunity to enjoy warm days on the water.
It’s not just on the lake where people gather but along the Chicago River running through the center of the city. Downtown dockage is available but tends to fill up fast so reservations are encouraged. Just like the lake, the boat traffic in the Chicago River gets congested during the season months and does require precautious boating.
Safety Requirements:
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Boating License/Education Rules: Valid Boating Safety Certificate issued by the Department of Natural Resources or an entity or organization recognized and approved by the Department is required.
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Life Jacket Requirements: 13 and under must wear a PFD.
For more information, visit the Illinois Department of Natural Resources.
Where to dock your boat, or meet your rental:
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DuSable Harbor
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Belmont Harbor
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Burnham Harbor
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Monroe Harbor
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East Chicago Marina
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Downtown Docks
Weather Conditions
Ask some Chicago locals, and they’ll tell you summers in Chicago can’t be beat. Temperatures in the Windy City start to warm up around mid-May and last through the end of August into the beginning of September—making the summer season ideal for boaters and sailors.
Avg. Temperature High: Peaks around 82°F in July
Avg. Temperature Low: Ranging between 54-61°F during fringe months like May and September
Avg. Water Temperatures in Lake Michigan during the Summer:
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40°F in May
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52°F in June
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67°F in July
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70°F in August
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66.7°F in September
Chicago Boating Highlights
Between May and September, life in Chicago centers around Lake Michigan. When planning your next Chicago boat rental trip, be sure to add these popular activities and locations to your itinerary.
Things to Do in Chicago by Boat
Cruise the Chicago River in Style
Ease your way slowly down the Chicago River and have a little self-guided architectural tour as you make your way around the city. Look up and admire the impressive Chicago skyscrapers from your boat. Along the way, you’ll cruise under Chicago’s 38 bridges connecting the city over the river. Many of Chicago’s historic buildings and sites can be seen from the river and makes for a great sightseeing tour.
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Moorage: Docktown Docks
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Wake zone: Yes
Navy Pier is the epicenter of the Chicago Harbor system. Take your rental in a loop around the pier into the Monroe Harbor and up along the coast of Lake Michigan. Rent a fishing boat to get a great catch during the daytime or rent a sailboat to watch the pier illuminate the water at night.
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Moorage: Closest dockage is at DuSable Harbor or Monroe Harbor
Go Sailing on Lake Michigan
Being that Chicago’s nickname is the windy city it’s no surprise that sailing on Lake Michigan is another favorite form of boating here. Toss the lines and cast your sails into the trade winds for a science sailing experience alongside Chicago’s shoreline.
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Moorage: Most, if not all, of Chicago’s Harbors can support sailboat dockage.
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Wake zone: Yes - in some areas
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Seasonality: Sailing season is year-round, but most Chicago sailors stick to a six month period between late spring and early autumn.
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Moorage: Closest dockage is at Jackson Park Inner Harbor
There's a good chance you pick up your rental boat from the marina at Jackson Park, and if not, it's still worth going down to this area of Chicago's waterfront to cruise around and take in the breathtaking views. It's one of the best spots for sailing in Lake Michigan.
Party in the Playpen
The Chicago Playpen is recognized as one of the city’s biggest boat party scenes and summer boating hotspot. Hundreds of boats come to the Playpen and raft-up side-by-side, creating one massive floatopia. The atmosphere is full of music of all genres blaring, smells of BBQ, and the roar of people laughing while enjoying a fun-filled summer day out on the water.
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Moorage: The closest marinas to the Playpen are DuSable Harbor to the south, and Belmont Harbor to the north.
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Wake zone: Yes
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MoorageThere are a variety of Chicago marinas to choose to depart from. When at the dive site, you’ll want to anchor or look for local mooring balls.
Chicago has over a dozen shipwreck locations that are active dive sites for avid scuba divers. Four of the most popular wreck sites include the Wells Burt, the Straits of Mackinac, the Thomas Hume, and the Wings of the Wind.
Got questions?
Frequently asked questions
How much is it to rent a boat for a day in Chicago?
The cost to rent a boat in Chicago starts at $100 per hour, depending on the amount of time that you would like to use the boat.
What is Black Yacht Weekend?
Black Yacht Weekend is a floating boat party on Lake Michigan against the stuning Chicago skyline. In 2025, Black Yacht Weekend is happening from Thu, June 19 to Sun, June 22.
Do you need a boat license to rent a boat in Chicago?
Anyone born on or after January 1, 1998 who operates a powered watercraft of 10hp or more needs a Boater Safety Certificate. If your rental is captained you do not need a safety certificate.
How much does it cost to rent a boat at a party in Chicago?
Chicago party boat rentals stat at $135 per hour. Party boats can be rented with or without a captain.
What are the top destinations to explore with a Chicago boat rental?
With a Chicago boat rental, top destinations include the Chicago River for stunning views of the city's iconic architecture and skyline. Lake Michigan offers a chance to anchor near Navy Pier or the lively Playpen area for sunbathing and socializing. North Avenue Beach and Montrose Beach are popular spots for swimming and relaxing just offshore. For a quieter cruise, head to Belmont or Burnham Harbor near Museum Campus. Each destination offers a unique way to experience Chicago from the water.
What is Chicago Scene Boat Party?
Chicago Scene Boat Party is an annual boat event on Lake Michigan. In 2025, Chicago Scene Boat Party is happening Fri, Jul 25 to Sun, Jul, 27 at The Playpen.
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