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Mark: Len is an amazing host and captain. I’ve never had such a warm welcome or heartfelt experience, not on the wooden felucca on the Nile, nor the canal boat in England, nor the gondola in Venice, nor on a pedal bike boat on the Chicago River, nor any of my friend’s boats, or 75 foot yacht, on either side of Lake Michigan. Len was the only 1 of 7 GetMyBoat operator to respond with a personal reply. After a couple messages via the app, I had the courage to book my first ever GetMyBoat boat. Len requested a phone call to touch base. 2 days later, he was walking down the pier to greet us and bring onboard. Len went over the safety rules and confirmed our preferences for the 2 hours. Amy/Brian: Captain Len is the ultimate power boat captain. He makes safety priority one. He shared rich details about the history of Chicago, was very hospitable and made the boat ride unforgettable. We’ve never had a better boat ride experience in Chicago and beyond. Steven/Kristi: “Captain Len wowed us with his knowledge of chicago history and the best views to enjoy on the water. We were impressed by his attention to detail and safety was his number 1 priority.”
Captain Bob is the GOAT! We love him! He was so accommodating and so much fun. He took us out on the lake and gave us a sight seeing tour. My guests from out of town had so much fun being on lake. He took us to see the Chicago lighthouse, Navy Pier, Planetarium, and Play Pen. Would definitely recommend!!
We had a brilliant time with Captain Bob - even though the boat is a speed demon (in a good way), he's got a background doing water rescues as a firefighter so we always felt like we were in safe hands. He's also got an encyclopaedic knowledge of Chicago history and some interesting stories about the city. He's also great at stopping at the scenic spots for the most memorable photos. Loved our trip - can't wait to go again some time.
My fiancé and I planned a engagement photoshoot, however, due to weather conditions not cooperating, Greg was so flexible at rescheduling with us. He made us feel very comfortable and gave tips on how to take the most beautiful photoshoot out of the beautiful scenery of the city. Would totally recommend him! By the way, the boat was spotless, so clean and so so beautiful😍
We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.
We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with taking the photos and positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.
Between the iconic river that weaves through the city and the vast expanse of Lake Michigan, Chicago is a wonderful destination to spend time on the water. If you’re visiting the Windy City during the summer and looking to experience boating, you can choose from amazing sailing trips, yacht charters, boats for watersports, and so much more.
Chicago is a sprawling city that is home to incredible dining, art, sightseeing opportunities, and outdoor fun. With unique neighborhoods and districts that celebrate an abundance of cultures, there’s something for everyone in Chi Town. Home to the iconic “Cloud Gate” (also known as The Bean) mirrored sculpture, Navy Pier, Wrigley Field, and the Willis (formerly Sears) Tower, Chicago is a must-see city for adventurous travelers looking to experience a little bit of everything in a bustling urban environment. Explore the riverfront, learn about the history of the city on an architectural tour, or book a boat party and experience the epic “Playpen” area of Lake Michigan.
The average rental duration for GetMyBoat bookings in Chicago — perfect for a sightseeing cruise as part of a day playing tourist.
These two months account for 65% of GetMyBoat trips in Chicago, with June and September rounding out another 30%. Outside of those months, it’s typically too cold to boat.
Summer is the best time to enjoy boating in Chicago! Due to strict city regulations, the official season runs from May 1st to October 31st when the harbors are open.
The busiest weekends on the water in Chicago are the 4th of July weekend, Memorial Day Weekend, Labor Day Weekend, and the annual “Chicago Scene Boat Party” weekend, which typically takes place in late July or early August. During the summer you can usually expect sunny and hot conditions, perfect for a day on the lake or the river.
If you’re looking to boat, the best time frame will be peak summer. From June to July, the weather should be warm and pleasant enough for you to enjoy a balmy, sun-filled day on the water.
Lake Michigan never gets all that warm, only reaching an average of 70ºF in August. July and September are similarly warm, around 65ºF — though if you’re used to warm Caribbean waters, it’ll certainly feel a bit bracing. Outside of those summer months, the temperature gets very cold, and of course, parts of the lake ice over in the winter.
Water temp.43 °F
WindSSW 18.27 f/sec
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 or first weekend of August. Plan ahead if you want to go — 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.
While Lollapalooza is not a boating event, it’s a top reason to come to the city during the summer months. Lollapalooza is a huge music festival that takes place annually in early August in Grant Park, drawing in crowds from all over the world for four days of music. Many people attend a select day or two of the festival and spend the rest of their vacation exploring other parts of the city — making it a great excuse for a boat tour.
A Labor Day weekend tradition in Chicago, the Jazz Festival brings together people from all walks of life to enjoy the many amazing sounds and sights that Jazz has to offer. The festival takes place in Millenium Park but bits and pieces of the celebrations can be found throughout the entire city in various neighborhoods.
The Chicago Boat Show typically takes place outside of boating season in January, but it’s a massive event for all boating enthusiasts in the city. See hundreds of boats and various booths, participate in fun events and activities (like remote control sailboat racing — extra fun for kids!) or stop at the indoor “beach bar” to get a reminder of what boating season is like during the winter months. The Chicago Boat Show takes place at McCormick Place and is sponsored by Progressive Insurance.
Chicago has plenty of different types of boats to rent: everything from pontoons to luxury motor yachts, sailing catamarans, fishing boats, and jet skis are available. Here’s a bit of information on the average prices, and more, for each different option.
Chicago is home to some gorgeous luxury yachts that can provide the ultimate cruising experience for a day on Lake Michigan. Let a captain and crew take care of your group as you soak up the sun and views of the skyline. Sip champagne and explore the river or cruise to the Playpen to see the other yachts and boats tied up and mingling on the water.
Looking to have a good time on the water? Celebrate a special event with a party pontoon in Chicago. Bring the drinks and toss them in the iced cooler, roll out a floating mat, and spend the day blasting music and partying with your favorite people on the water. Party barge pontoons are popular for bachelor and bachelorette parties, large birthday groups, and any other reason to celebrate on the water.
A houseboat is a boat that has been designed to have all the comforts of home — including bedrooms, bathrooms, a kitchen and living area.
A wake boat (sometimes called a ski boat) is a style of powerboat that is most often used for enjoying water sports like wakeboarding, waterskiing, wakesurfing, kneeboarding, and more.
Prefer to explore by wind? Sailboat rentals and sailing charters are a unique way to experience boating on Lake Michigan. Calmly cruise past views of the skyline onboard a sailboat. An experienced local skipper can teach you the basics of sailing and provide an unforgettable experience for you and your crew.
A catamaran can be power or sail-powered and is a vessel with two parallel hulls. Catamarans get their stability from the wide beam across the hulls. Catamarans are great party boats and for staying overnight on the water in Chicago.
A fishing boat is any vessel that is designed for fishing. They can have flat bottoms for inshore angling or be large charter boats used for deep-sea fishing.
Have a need for speed? Rent a jet ski and fly through the waves! Chicago is a great place to rent a jet ski and explore with a friend. Book a pair of jet skis for a few hours and cruise around the waterfront, it’s sure to be a thrilling adventure.
Looking to explore the area? Look no further! Thanks to its diverse stretch of over 70 neighborhoods and a rich waterfront area, Chicago is home to a wide array of spots that combine the best of both city life and boating culture. Here are some of the best to add to your list as reasons to visit the Windy City.
Enjoy waterfront views at this upscale establishment, which offers a unique twist on Classic British pub fare. Try the famous roast chicken and don’t skimp on dessert. Vegetarians need not worry — this place is known for its generous side portions of delicious roast vegetables.
For a premium dining experience, RPM Seafood offers seafood dishes, pastas, steaks, and a top shelf full bar. It’s located on the riverfront and offers a gorgeous patio setting, perfect for a beautiful summer day in Chicago.
Known for its dog-friendly atmosphere and gorgeous views of Lake Michigan, this cafe is a great spot to visit for a quick bite during the summer months. Enjoy casual dining of delicious sandwiches and burgers, and frequent live music on the shores of the lake.
Sip a craft beer and indulge in American classics at The Lakefront Restaurant. Located in Lincoln Park, you can enjoy upscale dining with views of both the skyline and the waterfront. Stop in for Brunch on the weekends or try their signature brisket and chicken dishes.
This walk-up restaurant offers delicious food, live music, salsa dancing, and stunning views of Lake Michigan from the 31st Street Beach. Enjoy a burger with a view of the skyline and the lake.
This sophisticated spot is located right at — you guessed it — the Navy Pier, with sweeping Lake Michigan views and easy access to all things boating once you’re done relaxing in your accommodations or exploring the city.
An upscale and trendy member of the Marriott family, W hotels are always a nice place to stay, and even more so at this location that’s located right in the Lakeshore neighborhood on the banks of Lake Michigan.
Part of the Marina City complex, one of Chicago’s many iconic architectural landmarks, this spot has a pitch-perfect view of, and access to, the Chicago River, so you can relax in the hotel lobby and watch the tour boats cruise up and down the waterway — and then get out onto the water yourself.
Right in downtown Chicago, this one sits at the foot of Randolph Street. It’s surrounded by Chicago’s famed downtown skyline, and since it’s the only harbor with slips close to the loop, it’s quite popular.
Located right in the heart of Lincoln Park, this is one of Chicago’s largest harbors and a longtime favorite of the locals. It’s got an especially nice surrounding environment, thanks to the acres of park space and the southward skyline view.
Another harbor located within Lincoln Park. Note that because of bridge restrictions, Diversey can only accommodate standard-sized power boaters — no large yachts or tall sailboats.
Rich with nostalgia and history, Monroe Harbor is an icon in Chicago boating. This spot and its 800+ mooring cans create an integral element of Chicago’s panorama as its boats float in the shadows of the city’s stunning skyline.
Walking distance to downtown, Burnham is located on the Museum Campus, and also happens to be the very largest harbor in the entire Chicago Harbors system.
The newest harbor, having been finished in 2012, the 31st Street Harbor boasts 1,000 slips and has a uniquely sustainable and eco-friendly design that also just so happens to be exceptionally convenient for boaters.
The classic Chicago boating experience: cruise all along the river waterways and scope out architectural gems that comprise the city’s iconic skyline.
Set sail towards the northern edge of the city and see this beautiful bird sanctuary from the water. Bring your binoculars!
A quaint and scenic picnic spot on a man-made peninsula just north of Jackson Park, it’s a nice spot to cruise around on a boat to see the landscape architecture from a different perspective.
Visiting for a special occasion? A corporate retreat? Bachelor or bachelorette party? Whatever your reason, take it to the water! There are all kinds of occasions that are better celebrated on a boat rentals while you’re in the Windy City.
One of the best ways to experience the water in Chicago and learn a lot about the history of the city is an architecture boat tour. Typically lasting around 90-minutes, these immersive boat tours will take you on a journey down the Chicago River where you’ll get a front row seat of the incredible skyscrapers and the views of the riverfront. See the world-famous landmarks of Chicago on a boat tour, and learn about their history, significance, and interesting details about the architecture. There are snacks and drinks available on most tours and you can kick back and relax, absorbing the city from a whole new perspective.
With its thriving bar and nightlife scene, high-end restaurants, and endless opportunities for entertainment, Chicago is a great place to venture to with your “I Do” crew. A day spent on a yacht cruising Lake Michigan with the guys can be the perfect activity to round out the weekend, and captains can bring iced down coolers, floating mats and toys, and provide the perfect experience for a party on the water. Don’t just go to the beach in Chicago — cruise right past it on your own private boat.
Planning a final “sail before the veil” with your favorite group of women? Any maid of honor can appreciate having a personal yacht captain available to help finalize all the details of the perfect bachelorette party boat day. Put on your matching swimsuits, pack your towels, sunscreen, and sunglasses, and celebrate with a skyline-backdrop photoshoot during your time out on the water, and then take the party to the city once you finish up on the boat with Chicago’s vibrant food, drink, and nightlife scenes.
Kanye West had his birthday party in Chicago — and you can too! If you’re a Chicago local and looking to celebrate a summer birthday (especially if it’s a milestone birthday) a boat rental or yacht charter on Lake Michigan is the perfect way to get together with people. Start the party early with a fun boat day, where you can float in the lake, enjoy drinks and food onboard, or even cruise to a waterfront restaurant for a birthday meal. Don’t forget the cake!
Planning to say “I do” in the city? Why not enjoy your special day on a boat? Chicago is a great destination for a wedding onboard a boat or yacht. A boat wedding in Chicago provides a unique point of view and a unique venue for celebrating your special day. Check out our guide to planning a boat wedding for more ideas and information.
It’s no secret that Chicago is a bustling business center. Whether your company is based in town, or if you’re arranging a company retreat to treat your employees to a day of fun in a new city, a large-group boat rental can be an excellent way to enjoy the Chicago views while having a relaxing, social time with your coworkers.
A note: if you’re renting a boat through GetMyBoat, please contact the boat owner before utilizing any of the following services. They may have a preferred provider or the services may be covered through insurance or within your rental agreement.
Professional boat towing services in Chicago.
2001 N Mendell St, Chicago, IL 60642 (866) 274-6302
Services include marine salvage, repairs, spill cleanup, towing, and battery jumps up to 50 miles offshore.
Offering marine HVAC, boat detailing, boat towing services, and graphics and stripping services.
35 E Madison St, Waukegan IL, 60085 (833) 737-3467
Marine repair services provider, known for their excellent customer service and knowledgeable mechanics.
5401 N Wolcott Ave #6, Chicago, IL 60640 (877) 649-1858
This boat repair company provides 5-star service in Chicago, offering boat storage, repairs, educational seminars, and is an authorized dealer for boat parts.
13535 S Forest Ave, Chicago, IL 60827 (773) 468-3776
This company provides not only boat and yacht repair, but full-scale yacht management from maintenance to operation. They offer crew services too.
207 E Ohio St #202, Chicago, IL 60611 (219) 743-2556
Crowley’s sells boat and engine parts, and provides services including rigging, mechanical repair, painting, systems services, hauling, and wood refinishing.
3434 E 95th St, Chicago, IL 60617 (773) 221-9990
This massive marina has over 1000 boat slips, a playground, and clean facilities. It’s operated by the city and often has live music from a DJ. It’s also noted as a good place to fish.
3155 S Lake Shore Dr, Chicago, IL 60616 (312) 225-6464
Right in the heart of downtown Chicago, DuSable has 420 boat slips and stunning views of the Chicago skyline. They offer no-charge waste pump out and a friendly dockmaster to help boaters get in and out.
111 N Lake Shore Dr, Chicago, IL 60601 (312) 742-3577
Burnham Harbor offers fuel and laundry services for boaters, transient slips, an on-site restaurant, and it is the largest of all the marinas in the city with 1,126 wet slips. This harbor is within walking distance of the Shedd Aquarium and other Chicago attractions.
1559 E Waldron Dr, Chicago, IL 60605 (312) 747-7009
Located in Lincoln Park, Belmont Harbor has over 800 slips. It is family-friendly and it offers dry storage in addition to wet slips, and transient docking services.
3600 North Recreation Dr, Chicago, IL 60613 (312) 742-7673
GetMyBoat is the world’s largest boat rental and water experience marketplace. We connect more people to boat rental services than any other company. Our mobile app available for iOS and Android makes it possible to find and book boating experiences right on your phone.
You can access thousands of professional boat captains and companies to help plan your perfect day on the water. GetMyBoat’s 24/7 customer service team is always available to help with any step in the booking process. We also enable you to read real user reviews and see photos added from past users, so you can book with confidence that you’re choosing a 5-star boat rental or water experience.
GetMyBoat is committed to taking the lowest booking fees in the industry to save the customer money in pursuit of their perfect day on the water.
A boat charter (vs. a boat rental) includes a professional captain to drive the boat. Frequently, it also includes crew members to provide services to the passengers, like food and beverage, as well as being there to assist the captain. The number of crew members working a boat charter will depend on the size of the vessel and the number of guests onboard.
A boat charter with a licensed, professional captain is the best option for inexperienced boaters or people unfamiliar with the waterways they wish to explore. A captain can provide an amazing experience on a private boat rental and help make the experience safer and more relaxing for boaters.
While half-day and full-day boat rentals are the most commonly booked trip durations on GetMyBoat, some boat owners and operators allow for multi-day or week-long rentals. Some owners and boat rental services offer discounted rates when you book for more than one day. Ask about weekly deals on rentals if you’re hoping to go boating for more than one day.
While it’s common to meet at a marina or public dock, boat captains and owners can often coordinate a drop off at a boat launch or ramp, or another spot if it’s more convenient. Get the exact directions to where you need to meet your boat owner/captain to determine where to pick up the vessel. Send your captain a message to clarify if you’re unsure where to go!
If you need to refuel your boat rental before you return to the dock, ask the boat rental service or owner where they recommend that you refuel. Most waterways will have several fuel stations to choose from, and often the docks that you meet at for your boat rental will also have them. Many captains and owners will take care of this for you, but it’s a good idea to ask what their specific policy is for fueling. Check out local marinas to see if they have a fuel dock.
Dogs are often welcome on boat rentals and charters — but be sure to ask first! Some boat captains do and some don’t allow pets to come along.
It’s also a good idea to do some research to make sure your pet will be okay with boating if they’ve never been before. Check out our guide for boating with your dog, and if you do decide to bring your dog along, make sure you have the appropriate lifejacket and other safety gear for them!
GetMyBoat’s mission is to make boating more accessible and affordable. To do this, we’re constantly growing our team of boat owners, captains, and operators around the world to offer a wider range of boat rentals and services at different price points. We want to provide the joys of boating to everyone - regardless of their budget.
Boat rental costs will vary depending on the size and type of boat you wish to rent. Other factors that impact the price of a boat rental include: trip duration, desired route, and itinerary. A boat rental usually costs between $50 and $150/hour but can range up to over $400/hour. Renting a boat for a few hours is usually less expensive than renting a boat for a whole day, but you can sometimes save money on the hourly rate by renting for longer - some owners and rental services offer discounted rates.
There’s no booking obligation at the inquiry stage with GetMyBoat - so you can send an inquiry message to a captain to get a price quote before you commit.
The cost of a boat rental will depend on the duration of your rental, the size of the boat, and the size of your group. Sometimes, specific itineraries (i.e., traveling far distances to get to a famous swimming spot) can add extra costs if they require additional fuel. Typically, a half-day boat rental is 4-hours, and a full-day is 8 hours. Depending on your specific needs, you can expect to pay anywhere from $250 to over $1000 for your boat rental.
Boat rentals on the Chicago River start at around $100/hour and can range from there to over $500/hour for a larger yacht. You can find boat tours of the Chicago River for as affordable as $40/person, but this is generally with a larger public group and not an individual boat rental.
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.
Yacht rentals in Chicago start at around $250/hour and go up to over $1,000/hour depending on the size of the vessel, capacity, and special features.
A boat rental on Lake Michigan typically costs between $150-300/hour, but it can vary depending on the size of the boat, the day it is rented (weekdays are typically more affordable, and holiday weekends are very expensive), as well as other factors that impact cost. Expect to pay between $500-800 for a half-day boat rental on Lake Michigan.
When a captain and crew provide excellent service on the water, leaving a gratuity as a show of appreciation is a common custom. In many places, 10-20% of the rental cost is standard, but this can vary depending on where you are using boat rental services. GetMyBoat does not handle tips or gratuity payments, so please bring cash with you to tip, or many boat captains also have the option of CashApp or Venmo for leaving a tip after your boat charter.
Sometimes the boat owner/captain you are renting from will include fuel costs in the total fee charged, while others will charge on a usage basis - so depending on how much you use on your boat day. Inquire with the boat owner/captain about the typical fuel costs for your boat rental duration.
Costs for your boat rental will vary from owner to owner, so be sure to inquire about any extra costs that might not be covered in the listed price - like fuel, captain’s fees, or additional charges for unique itineraries. Your captain will let you know what to expect if there is any deviation from the price on the boat listing.
You must be at least 18 years old to rent with GetMyBoat. To operate a boat without a captain, you will need to ensure you meet the correct boating safety requirements. Boat owners and operators on GetMyBoat sometimes have their own individual age requirements for renting, so inquire with them on their minimum age when you send a booking inquiry.
To rent a jet ski independently, you have to be at least 18 years old. Often 16 & 17 year olds can operate a jet ski rental if they have a guardian present to sign a waiver for them. No one under the age of 16 should operate a jet ski without being in direct supervision of a parent or guardian.
The boat's capacity will vary depending on the captain’s licensing rules, size of the boat, style of the boat, and the location you’re renting in. Every boat listing on GetMyBoat indicates the maximum number of people allowed on the boat, so you’ll know before inquiring if it will suit your group’s size.
Whether or not you rent a boat with a captain will depend on many factors. If you do not have boating experience - it is recommended that you book a boat rental with a captain service for safety. Some locations require that renters have a licensed captain onboard operating the boat at all times. If you do have boating experience and want to rent a boat without a captain, in most locations you are able to rent it bareboat to go on your own. Ask the boat rental service provider for information on renting a boat without a captain and let them know information about your boating experience.
When you rent a boat, it’s a great idea to do some research on your own or ask the boat owner/company for recommendations if you’re not from the area. With a boat rental, popular places to venture to include sandbars, islands, beaches, coves, and waterfront restaurants. It’s a good idea to inquire with the boat owner for recommendations on what to do and advice on navigating there safely.
You do not need your own insurance to rent a boat.
Most boat owners and boat rental services will include all lifejackets and safety equipment within the price of your listing. It’s always a good idea to ask where the equipment is located onboard before you leave the dock. Your captain or the owner should give you a briefing at the beginning of your rental experience, so you’re aware of all safety features and equipment on the boat.
To rent a boat in Chicago you must be 18 years of age and have completed a boater safety education course. If you have a boating license from another state, this can apply to the requirements to rent a boat in Chicago.
Many boat safety courses are offered online and you can earn a certificate that will qualify you to rent a boat on your own. You can also often take in-person boating lessons which will teach you the necessary hands-on skills to operate a boat independently. Check out BoatEd for more information on local boating safety requirements and courses. You can also check out our Top Boating Safety Tips resources.
Boat license rules depend on your age. If you were born after 1988 you will need to complete a boat safety education course and receive a safety identification card. Check out BoatEd for more information on earning a boat safety card so you can rent a boat in Chicago. For more information please check out our Boating Laws and Regulations by State Guide and download our Boating Safety Checklist.
A Boater Education Card will cost anywhere from $0-$50 depending on the type of test you take and if you want your ID card professionally printed.
A Boating Safety Education Identification Card has no expiration date, however, the temporary safety course certificate (proof of online course completion that you can print out and use before the ID card comes) expires after 90 days.
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