small sailboat rental chicago

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CHICAGO'S TOP BOAT RENTALS

When you rent a boat from chicago sailboat & yacht charters, we provide the best variety, service, and value for any charter or rental boat experience you desire., chicago's top sailboat & yacht rental.

Whether you are looking for a romantic sailing trip for two, a sailboat for up to 11 people, power boat rental for up to 12 people, or a party boat rental for up to 36, Chicago Sailboat Charters & Rentals has the perfect charter for you, every day of the week!

HOW TO BOOK YOUR BOAT CHARTER ONLINE

Step 1: Use our online booking platform (click HERE ) to select your date and view charter availability.

Step 2: Once you select your charter, reserve and pay directly online in less than 60 seconds.

Step 3: After booking, refer to your confirmation email for instructions on how to book a captain.

WHY CHICAGO SAILBOAT CHARTERS?

Chicago Sailboat Charters offers Chicago's largest variety of captained charters for sailboats, yachts, and spacious boats, accommodating groups of 1 to 36 people. Enjoy daytime sailing, sunset cruises, swimming and sunbathing sails, or even witness the spectacular Navy Pier fireworks from our boats.

OUR SAILBOAT & YACHT RENTALS ARE PERFECT FOR...

Swimming & playpen, navy pier fireworks, chicago river cruises, celebration events, corporate outings.

773-236-724 5

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MAILING ADDRESS

400 West Belmont Harbor Drive, Chicago, IL 60657

773-236-7245

Belmont Harbor

Directions →

Dusable Harbor

Best Chicago Boat Rentals and Yacht Charters

• Boat Rentals
• Illinois Boat Rentals

Top Boat Rentals and Yacht Charters in Chicago, IL

Chicago, IL

37' Yacht - Includes Gas & Lily Pad! One Big Outdoor Seating Area!

Welcome to Victory at Sea! Let's cruise!

27' Chris Craft with Water Toys plus Jet Ski Available

New listing 40' Regal luxury Yacht

33ft Bayliner available for events and parties

Set Sail from Downtown Chicago!

Luxurious 60' Yacht with Flybridge for Up To 13 People!

Luxury 2010 Multi Level Yacht Safe Burnham East Dock 5 Star Service

The Spectacular SEA RAY 40 SUNDANCER - ICEMAN IV

Boatschicago - Motor Boat for rent at Downtown Chicago

Private sailing cruise for up to 6 people

46' Beautiful Sea Ray Yacht - Perfect for Parties - Explore Chicago

Gorgeous 40FT Sea Ray

Playpen, Skyline, River Tour and Fireworks Show w/o Captain Fees*

Sea Ray SunDancer (You Capt or Hire a Capt)

Private Sailboat Cruise in Chicago

Rent this 45' Sea Ray and Enjoy Chicago! - Perfect for Parties

Party boat with waterslide! 12 Guests

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

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Rent a Boat in Chicago

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:

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.

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:

DuSable Harbor

Belmont Harbor

Burnham Harbor

Monroe Harbor

East Chicago Marina

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: 

40°F in May

52°F in June

67°F in July

70°F in August

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

Moorage : Docktown Docks

Wake zone : Yes

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.

Hours : Varies by location - see each location for details (Pizzeria Portofino/RPM Seafood, Rockwell on the River, City Winery)

Lat/Long : 41.8870° N, 87.6290° W

Google Maps Link

Go Sailing on Lake Michigan

Moorage : Most, if not all, of Chicago’s Harbors can support sailboat dockage.

Wake zone : Yes - in some areas

Pro Tip s: If you’re in search of a Boatsetter Sailing rental, be sure to check out boats listed near Monroe Harbor or 31st Street Harbor.

Seasonality : Sailing season is year-round, but most Chicago sailors stick to a six month period between late spring and early autumn.

Lat/Long : 41.8781° N, 87.6298° W

Party in the Playpen

Moorage : The closest marinas to the Playpen are DuSable Harbor to the south, and Belmont Harbor to the north.

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!

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.

Lat/Long : 41°53'53.2"N 87°36'43.1"W

Where to Go Boating in Chicago

Moorage : Closest dockage is at DuSable Harbor or Monroe Harbor

Pro Tips : Summer Fireworks at Navy Pier are every Wednesday and Saturday from Memorial Day through Labor Day. 

Hours : Opens daily at 10am, but closing times vary by season.

Lat/Long : 41.8919° N, 87.6051° W

Jackson Park

Moorage : Closest dockage is at Jackson Park Inner Harbor

Wake zone : Yes

Pro Tips : There are 192 slips, mooring cans, and star docks, and the harbor can accommodates boats measuring 25’ to 40’ in length.

Hours : May 1-Oct. 31 - Open Wednesday to Sunday from 10am to 6pm; Closed on Mondays and Tuesdays.

Lat/Long : 41.7833° N, 87.5783° W

Lake Michigan Dive Site

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.

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.

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.

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)

Check Out Additional Chicago Boating Guides

• Boating Lake in Illinois
• 12 Best Chicago Restaurants on the River
• 6 Best Beaches in Chicago
• Lake Michigan Fishing Guide
• Chicago's Green River: St. Patrick's Day History & Boating Guide

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.

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.

Top boat rental reviews in Chicago, IL

46' Beautiful Sea...

Nasco was quick to respond to any questions and was very helpful! The boat was gorgeous, clean, and had more than...

Luxury 2010 Multi...

Great boat and crew! Had a great moment with family!!

Private Sailboat...

Jim and his crew were fabulous. We actually got upgraded to a nicer bigger boat too! They were very helpful to our...

37' Yacht -...

Theresa was a great host and was very communicative and helpful making sure everything was booked appropriately...

Set Sail from...

Dawn and her husband were professional, fun and friendly. Our group had a great time!

Dan was so communicative and helpful both before and after the event. Our captain and crew, Jason, Laurie, and Cam...

Luxurious 60'...

We had an exceptional experience with our boat charter! As someone who had never booked a boat before, I didn't know...

Outstanding evening with our Captain and Bartender! We had a great time , very smooth process from the moment we got...

27' Chris Craft...

Capital Tim Jr is great

Rent this 45' Sea...

Tim Jr. was a wonderful host. The boat was very well kept. We really enjoyed our excursion. It’s a great way to...

Boat rentals in Chicago, IL

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The Best Boat Rentals in Chicago

Browse, book, and get out onto the water with local captains and boat owners., our favorite boat rentals in chicago.

4.9 (5,133 reviews)

• Boat Rentals

the United States

Luxury 31ft for your Playpen Party

24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

*Embark on a Luxury Lake Michigan Adventure: Rent Our Stunning 2006 Rinker Fiest

25.5 ft. Chaparral SSX257 Luxury Vessel

Stunning 45’ Sea Ray Yacht

27' Maxum 2400 Motor Yacht Rental in Chicago

Double Decker 50FT Sea Ray Flybridge Yacht!

Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago

Playpen bound on 25' Yamaha Jetboat!

Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

45ft Sea Ray 400 EC Big Boat Small Price Everyone Can Enjoy! END OF SUMMER SALE

Suggested searches, types of boats popular in chicago.

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

₽16,110-₽78,760

Explore local waters with a boat rental dedicated to sightseeing and exploration

₽15,220-₽62,650

Set sail with these traditional wind-powered boats

₽11,190-₽33,120

Perfect for casual cruising, sandbar stops, swimming, and parties

₽10,740-₽71,600

Who says you need a motor to have fun on the water?

₽4,480-₽44,750

Fast, fun, and easy to operate, these are a guaranteed good time on the water

₽12,980-₽16,110

• Fishing Charters

Let a captain do the driving while you do the fishing

₽6,710-₽17,900

All the comforts of home out on the water, for multi-day boat trips

₽31,330-₽67,130

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

Most Popular Yacht Rentals in Chicago

36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

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

44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!

Captain Memo's 28 ft. Sea Ray in Chicago

Most Popular Boat Tours in Chicago

Burnham Harbor, CAPTAIN/FUEL INCLUDED

Willard Marine SeaForce!! Former Military Adventure Boat!

Captain Included. Escape the ordinary and cruise on 28’ Sea Ray of fun!

44' Italian Luxury Azimut Premier Party Yacht up to 13 plus Jet Ski Available

Most popular sailboat rentals in chicago.

Sailing Lessons with Chicago's #1 Rated Sailing School

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois

40' Sailboat Monroe Harbor Chicago

Recent reviews in chicago.

An overall wonderful experience! Communication was great with the captain from the start as he guided us through the phone to find the boat, the boat itself was clean with excellent service from the Bluetooth speaker to the cooler with ice; It was a Saturday night so witnessing the fireworks on the water is definitely a 10/10, my toddler very much enjoyed it as well! Thank you captain Memo 😊

Memo was a great captain! We appreciated his communication immediately upon booking all the way through our reservation. Throughout our trip, he made sure the experience was exactly what we wanted. Would definitely recommend him to anyone looking for the ideal Chicago boating experience.

46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

We had the absolute BEST time with Captain Kevin, Captain Steve, and Skipper Manny for my bachelorette party! Even despite the choppy water, they made sure to keep us safe AND have a great time. I wish I could give them 6 stars. 10/10 recommend!!

My bachelorette crew and I had a phenomenal time out on the water. Weather was great, vessel was great, and we made some lifelong memories! Will definitely be back on the waters of Lake Michigan soon. An activity worth doing if you’re making a trip to Chicago.

Last Minute Playpen Clean Beautiful Boat LOA 40' Sundancer

Rented Peter’s boat for a Bachelorette party and had such a blast! Peter was wonderful to deal with and communicated and arranged everything perfectly. Our captain for the day, Alex, was awesome and made all our first time in Chicago unforgettable!! Will be back next time we are visiting the city for sure!

We had an Amazing time with Memo on his boat! We connected really well with our captain which I believe is really important to having a great time, the boat was very fun and Captain Memo accommodated all of our wants and needs, we will definitely be back and book with Memo again!

Top Boat Rental Locations in the United States

Miami , Florida

930 listings

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434 listings

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447 listings

Los Angeles , California

405 listings

Hollywood , Florida

276 listings

Fort Lauderdale , Florida

250 listings

How To Book on Getmyboat

Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.

Inquire & Book

Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

Dive into Our Journal

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May 03, 2023

The Best Bachelor Party Destinations for Boating

October 11, 2021

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4th of July Boating Guide - Getmyboat

Frequently asked questions.

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 .

A smaller 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.

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

• Chicago Architecture Tour
• Cruise The River
• Shoreline Tour

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.

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.

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.

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

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.

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ON A BOAT SAILING

Luxury sailing adventures along chicago's lakefront, what makes  on a boat sailing different.

If you appreciate attention to detail, hospitality, and thoughtful amenities, this is the group experience for you! Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since 2018. As we hit the waterfront for our 7th season, we pride ourselves on offering an unforgettable way to experience Lake Michigan from the City.

The Crew - Captain Greg & 1st Mate Cait

Our crew have a combined 25 years sailing experience, allowing us to curate the best possible experience for our guests. Sit back & relax as you take in the sights & sounds of Chicago's famous Lakefront.

The Yacht - 2003 Jeanneau Sun Odyssey 37

S/V Dragonfly was built for day cruises & entertainment. Our 37' luxury sailboat is a fantastic venue for any special occasion. We are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the US Coast Guard.

Learn more about our crew and yacht   here .

Whether you're getting on the water for the first time or a seasoned boater, our focus is to curate your special outing with world-class sailing, comfortable amenities, and incredible views of Chicago's famous Lakefront.

2024 bookings are available from Memorial Day weekend to mid-September with multiple departures daily from centrally-located Monroe Harbor in Downtown Chicago . Please visit our all charters page to learn more about our one-of-a-kind sailing adventures. Chicago is the best place to combine the thrill of sailing with views of a city steeped in rich architectural history - let us show you. Cheers! Captain Greg & First Mate Cait

OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018

Chicago sailboat  charters & cruises, limited weekend bookings available - book now, sail & swim playpen charter.

USCG Captain

Chicago's famous lakefront party is back! This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, with a good mix of adventure sailing on Chicago's Lakefront along with dropping anchor at the Playpen or a private area of your choosing. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

  $1,399 | Up to 7 Guests  

Fri • sat • sun departing 10am & 2:30pm.

Navy Pier Fireworks Cruise

Uscg captain .

This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.

$999 | Up to 7 guests 

Wed  7pm •   sat  8pm.

“I rented [Dragonfly] 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!

Dyna, Chicago, IL

Chicago Lakefront Cruise

This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience- this is the cruise for you.

$899 | Up to 7 guests

WED • FRI • SAT • SUN Departing 10am, 1:30pm & 5:00pm

Skyline Sunset Cruise

Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.

$799 | Up to 7 guests 

FRI • SUN Departing 6:30pm

PLAN YOUR CHICAGO SAILING ADVENTURE  TODAY!

Explore world-class sailing, Great Lakes swimming & luxury amenities all summer long.