yacht rental chicago prices

Find the best boat rentals in Chicago, IL

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Top Boat Rentals and Yacht Charters in Chicago, IL

Chicago, IL

BIG BOAT at small boat price.

The Best Playpen Party Boat in Chicago! Captain included!

Chicago's Largest Chartered Catamaran, "Latitude Adjustment"

New 27' Sea Ray crusier Playpen summertime

Beautiful Yacht -comfortably accommodate up to 12 guests. Perfect for

Classy Carver Mariner Yacht w/Flybridge

Charter boat available with Captain Bob

Private Sailboat Cruise in Chicago

The Spectacular SEA RAY 40 SUNDANCER - ICEMAN IV

Playpen bound on 25' Yamaha Jetboat!

50' Luxury Yacht. Playpen, River cruises up to 12. Captain included!

Welcome to Victory at Sea! Let's cruise!

FREE HOUR MONTH OF SEPTEMBER AND OCTOBER -CAPTAINED!!!!NEWER BOAT!!!

Affordable Luxury - 40' Spacious Boat w/ Floaty

62' $2M Italian Luxury Yacht with Captain Party up

The Exciting Sea Ray 39 Sundancer - ICEMAN

The Beautiful Sea Ray 38 Sundancer - ICEMAN II

Sea Ray 38 Sundancer, Perfect for the Play Pen - ICEMAN III

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.

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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

New 27' Sea Ray...

We had the best time out on the water! We brought a couple from out of town, and William was fantastic with...

BIG BOAT at small...

This boat set up was amazing. Spacious for our group of 12, couldn’t ask for a better time on the boat! Garland was...

Affordable Luxury...

Me and my girls had a blast …. We will definitely be back and Captain T was wonderful 🛥️🍾❤️

50' Luxury Yacht....

Great experience...will do it again

The experience on the boat was great! Would 100% recommend booking William's boat for a bachelorette party.

We had a one in a life time experience, we enjoy the moment a lot with our family, great service and thank you...

Welcome to...

Our boat ride was very pleasant. Captain Eric was very helpful the whole trip. We anchored by lakefront. Skyline...

Beautiful boat and great time with captain Jim

The Best Playpen...

We had so much fun! Ted made booking very easy and communicated great. Mark was a fantastic captain.

Good communication, nice boat, great help

Classy Carver...

Great boat nice spacious and Host was amazing.

Private Sailboat...

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

Boat rentals in Chicago, IL

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 22 boat rentals & yacht charters in chicago, il.

Chicago, IL

boating guide

In addition to the best offers we have for boat and yacht charters in Chicago, IL, see also options available for rent in these nearby locations:

• 22 boat rentals in Chicago Loop, Chicago, IL
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• 22 boat rentals in Near North, Chicago, IL
• 22 boat rentals in Little Italy, Chicago, IL
• 22 boat rentals in West Loop, Chicago, IL
• 22 boat rentals in Near North Side, Chicago, IL
• 22 boat rentals in Gold Coast, Chicago, IL

Rent a Luxury Yacht Charter in Chicago, IL with Sailo!

Choosing a luxury yacht rental in Chicago, IL? Enjoy the freedom of the open water on a private boat rental in Chicago, IL from Sailo. Rent a boat from a couple of hours to a full day, to really explore Illinois from Chicago. With a licensed captain driving your boat rental with, you’ll be able to relax and discover those hidden gems with your friends or family. Prefer to skipper your yacht rental? Use our advanced filters to find your perfect bareboat charter on Sailo!

Our premium selection of private boat rentals in Chicago, IL

There are currently 15 Sailo Chicago yacht charters waiting for you in Illinois. From a day trip on the water, to a week exploring (or more), it’s easy to find the perfect boat for you on Sailo. Our inventory includes boats for Chicago sailing waiting to take you away. You’ll find Chicago catamaran rentals and charters in Illinois. If you prefer boating in Illinois you’ll also have the choice of Chicago motor boat rentals for an unforgettable trip. Throw the party of the year in Illinois on the deck of your own party boat rental suitable for more than 13 guests: search the Chicago party boat rentals with Sailo and book the one for you.

How to find the perfect boat charter for Chicago for sailing?

Sailo has the most advanced filters to help you find the perfect boat charter in Chicago for an amazing experience on the water in Illinois. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by Chicago boat rental type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Illinois, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much does it cost to rent a yacht in Chicago for a day?

Whether you are looking to rent a yacht for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Chicago sailing is $1100. You can however find excellent affordable rentals from $250 and also elegant Chicago yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I rent a boat in Chicago with a captain?

When you rent a Sailo boat rental in Chicago with captain, you set yourself and your guests for a relaxed, worry-free trip, with a professional skipper making sure that you all have an amazing experience on the water. Currently we offer 14 boat and yacht rentals with captain in Chicago for sailing.

Sustainable yachting tips

If you’re looking to explore our beautiful planet, a boat rental in Chicago is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:

• Don’t disturb coral or sealife
• Take your trash home (and don’t throw anything in the sea)
• Respect the locals and their customs wherever you go

Read more about responsible boating.

Popular locations to rent a boat on the Midwest USA:

• Rent a boat in Detroit
• Cleveland yacht charters
• Michigan boat charters
• Rent a boat in Ohio
• Traverse City boat rentals
• St Clait Shores boat rental

Popular boat types among renters:

• Party boat rental Detroit, Michigan
• Cleveland sailboat rental
• Party boat rental Cleveland, OH
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The Best Boat Rentals in Chicago

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

Boat Rentals Available for Instant Booking in Chicago

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

42ft Searay Sundancer | Big Boat Small Price END OF SUMMER SALE!

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

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

Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

62' $2M Italian Luxury Yacht with Party up to 12

Yamaha Waverunner FX Cruiser HO Chicago IL

Our favorite boat rentals in chicago.

4.9 (5,084 reviews)

• Boat Rentals

the United States

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

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

Stunning 45’ Sea Ray Yacht

25.5 ft. Chaparral SSX257 Luxury Vessel

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

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

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!

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

20 Passenger Captained Party & Event Boat in Chicago

Suggested searches, types of boats popular in chicago.

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

₽17,240-₽93,700

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

₽16,480-₽65,910

Set sail with these traditional wind-powered boats

₽11,590-₽35,640

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

₽11,500-₽76,640

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

₽4,790-₽26,820

• Fishing Charters

Let a captain do the driving while you do the fishing

₽6,420-₽19,160

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

₽14,370-₽17,240

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

₽33,530-₽71,850

Fishing Boats

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

Most Popular Yacht Rentals in Chicago

2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

NEW!!! 35' Luxury Motor Yacht with 4’ swim platform. Get 10% off for Weekend

Bayliner Ciera Motor Yacht Charter in Chicago, Illinois

2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024

Most popular boat tours in chicago.

NEW!!! SPACIOUS 40ft Cruisers Yacht, Power…in the Lake, Chicago

Hop abroad the Malort Missile luxury 31' Formula - Perfect for the Playpen

Experience Lake Michigan like never before on Beautiful 35ft Maxum

Sailing Lessons with Chicago's #1 Rated Sailing School

Most popular sailboat rentals in chicago.

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

Set Sail with 36' Sailing Boat in Downtown, Chicago

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

Private Cruise onboard Hunter Legend Sailboat in Chicago

Recent reviews in chicago.

Captain Memo's 28 ft. Sea Ray in Chicago

An awesome experience - right from booking the trip, the trip itself, and the warmth and responsiveness of Capt Memo. The boat was awesome - clean and with space up front and in the back of the boat. Capt Memo asked us upfront how we wanted to spend our time and ensured we got exactly what we wanted. He also took some great pictures which he shared promptly. And he engaged with us when we welcomed it but also gave us space when we wanted it. All in all, we loved the experience and will certainly be back

70' EXCLUSIVE Motor Yacht NEW to Chicago

Damian and Monica (and Jimmy) were a pleasure as captain, staff, and assisting with our trip. Everything was on time and their initial instructions were easy to understand and friendly. Our trip included both the the river and lake and was a beautiful day. Our originally scheduled Saturday had bad weather forecasted and we were lucky enough to reschedule for the day after. This was a surprise for my Mom and when the boat arrived it was huge, clean and ready to go. We brought our own food, drinks, and also had the ability to play our own music. The boat was the biggest on the water and we loved the multiple locations on the boat to hang out to eat and drink. It was an unforgettable day and I would not hesitate to use them again. I highly recommend it!

Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat

Jason has very competitive pricing that is well worth it. Communication was very easy. He provided me with a very simple list to find a captain (which was the piece I was most worried about). The boat came with ice and cups which made it so easy for hosting. Had a great time!

We had an amazing time on Jason’s boat celebrating a 30th birthday! Our captain Justin was phenomenal. Everything was just as it was on the listing. Boat was clean, as was the bathroom. Ice and coolers were provided as well as kitchen utensils. An amazing deal comparatively. Wouldn’t change a thing! Thank you Jason and Justin!

We rented out this yacht for my boyfriend’s birthday party! The boat was spacious and just as described. Our captain Peter and his wife were an amazing crew, thorough with safety, attentive, and went above and beyond to make sure that we had an incredible time! Booking with Eugene was a breeze, he was quick to respond, as well as answered every question that I asked! Everyone had a blast, and we will definitely be booking through them again!

Jason’s boat was perfect for my birthday! Great communication with a good list of drivers! Loved the amount of seating & the driver (Justin) took a great route with perfect views!

Top Boat Rental Locations in the United States

Miami , Florida

926 listings

Miami Beach , Florida

420 listings

Tampa , Florida

443 listings

Los Angeles , California

415 listings

Hollywood , Florida

270 listings

Fort Lauderdale , Florida

249 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!

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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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Yachts and boat rentals in chicago, our yacht fleet.

Welcome to Windy City Yacht Rentals, your premier choice for boat rentals and luxury yacht experiences in Chicago. We offer a wide range of boats and yachts for all your boating needs, whether you’re planning a corporate event, a private celebration, or simply a day out on the beautiful waters of Lake Michigan.

As the top boat rental service in Chicago, we take pride in providing our clients with unforgettable experiences. Our experienced captains and crew are dedicated to ensuring your safety and comfort while delivering exceptional service throughout your journey. Whether you’re cruising along the magnificent Chicago skyline or exploring the serene waters of Lake Michigan, our team is here to make your boating experience extraordinary.

Discover the true meaning of luxury with our sophisticated yachts, perfect for hosting private parties or corporate events. With spacious decks, elegant interiors, and top-notch amenities, our yachts provide the ideal setting for creating lasting memories. From intimate gatherings with friends and family to grand celebrations, we have the perfect yacht to meet your needs.

At Windy City Yacht Rentals, we understand that every event is unique, and we offer customizable packages to cater to your specific requirements. Our dedicated team will work closely with you to curate a personalized experience, ensuring that every detail exceeds your expectations.

Experience the thrill of cruising the waters of Lake Michigan, taking in the breathtaking views of Chicago’s iconic skyline. Whether you’re seeking a peaceful day of boating or an exhilarating party on the water, our boat rentals and yacht charters offer a variety of options to suit your desires.

Make your reservation today and let Windy City Yacht Rentals provide you with an unforgettable boating experience in the heart of Chicago.

Prices incude All captain, gas, and docking fees

Get a Price Quote

Looking to book your next charter, book your charter online.

Use our easy online booking platform (by clicking   HERE ) to select your yacht, date, and time directly online in less than 60 seconds. 

HIRE YOUR CAPTAIN

After booking, you will receive a confirmation email with instructions on how to hire a captain from a list of approved operators.

ENJOY THE WATER!

Refer to your confirmation email for directions, items to bring, and safety information. Enjoy the day on the water with your hired crew!

Testimonials on Windy City Yacht Rentals

As featured on:.

• Bachelor Parties
• Playpen parties
• Birthday Parties
• Fireworks At Navy Pier
• Romantic Dinners With A View
• 44′ SEARAY SUNDANCER
• 44' SEARAY EXPRESS

Book A Charter

Rentals accommodate up to 1 charterer + 12 passengers. Captain is not included. Captains generally charge $80 to $120 per hour.

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Dock Address

3155 S Lake Shore Drive Chicago IL 60616

Corporate Office

350 N La Salle St #420 Chicago, IL 60654

The information on this website is for general information purposes only. Nothing on this site should be taken as professional advice for any situation. By using this website you agree to our privacy policy, terms & conditions, and cancellations policy.

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