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Private Sailboat Cruise in Chicago
How to rent a boat in Chicago?
Find the perfect boat
Enter your desired location and date to explore our fleet of boat, Chicago, IL, United Statess.
Select a captain
Choose to drive yourself or select a USCG licensed captain.
Book with ease
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Set sail
Enjoy your day on the water with friends and family!
Rent a Boat in Chicago
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.
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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
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Pro Tips: Docking reservations at the Downtown Docks, while transient, are only for 2-hour durations. Plan ahead and submit reservation requests 2 weeks or less before your arrival.
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Hours: Varies by location - see each location for details (Pizzeria Portofino/RPM Seafood, Rockwell on the River, City Winery)
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Lat/Long: 41.8870° N, 87.6290° W
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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Pro Tips: If you’re in search of a Boatsetter Sailing rental, be sure to check out boats listed near Monroe Harbor or 31st Street Harbor.
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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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Lat/Long: 41.8781° N, 87.6298° W
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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Pro Tips: The Playpen is the go-to destination during Chicago’s annual Boat Scene Party, with over 10,000 attendees and 500-1000 boats tied up. Secure your boat rental early for this event!
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Seasonality: Thousands of boat drop anchor in the Playpen each year, with peak season for this location ranging from Memorial Day weekend through Labor Day.
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Lat/Long: 41°53'53.2"N 87°36'43.1"W
Where to Go Boating in Chicago
Navy Pier
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
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Wake zone: Yes
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Pro Tips: Summer Fireworks at Navy Pier are every Wednesday and Saturday from Memorial Day through Labor Day.
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Hours: Opens daily at 10am, but closing times vary by season.
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Lat/Long: 41.8919° N, 87.6051° W
Jackson Park
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.
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Moorage: Closest dockage is at Jackson Park Inner Harbor
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Wake zone: Yes
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Pro Tips: There are 192 slips, mooring cans, and star docks, and the harbor can accommodates boats measuring 25’ to 40’ in length.
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Hours: May 1-Oct. 31 - Open Wednesday to Sunday from 10am to 6pm; Closed on Mondays and Tuesdays.
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Lat/Long: 41.7833° N, 87.5783° W
Lake Michigan Dive Site
Much of Chicago’s history lies under the waters of Lake Michigan, resting just off the shores of the city's popular lakeside beaches. Chicago has over a dozen shipwreck locations that are active dive sites for avid scuba divers. Many of the wreck sites date back to the 1800’s when Chicago was one of the busiest shipping ports in the country.
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Moorage: Depending on which dive site you’re interested in, there 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.
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Wake zone: Yes
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Pro Tips: Four of the most popular wreck sites include the Wells Burt, the Straits of Mackinac, the Thomas Hume, and the Wings of the Wind.
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Hours: While it is possible to dive year-round, Lake Michigan peak recreational dive season falls between May and ends in early November. Visibility varies, but divers can generally expect 35 to 40 feet—or on clear days up to 100 feet.
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Lat/Long: Wells Burt (42° 2.748' N, 87° 37.082' W); Straits of Mackinac (45°48′51’ N 84°44′56’ W); Wings of the Wind (41°56.089’ N 87°33.391’ W)
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 $75 per hour, depending on the amount of time that you would like to use the boat.
How much does it cost to rent a boat on the Chicago River?
The cost to rent a boat on the Chicago River starts at $75 per hour, depending on the amount of time that you would like to use the boat. Rent jet skis, sailboats, yachts, and more along the Chicago River.
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 a yacht rental cost Chicago?
The cost to rent a yacht in Chicago starts at $275 per hour. The cost varies depending on the boat size and length of the trip.
Top boat rental reviews in Chicago, IL
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5/5 stars
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5/5 stars
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5/5 stars
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5/5 stars
I had a fun time! Captain Tiffany was great!
yong
Sep 2022 -
5/5 stars
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5/5 stars
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5/5 stars
Adekunle
Sep 2022 -
5/5 stars
Siobhan
Sep 2022 -
5/5 stars
Danielle
Sep 2022 -
5/5 stars
Nadia
Sep 2022 -
5/5 stars
Josh
Sep 2022 -
5/5 stars
Abby
Sep 2022
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