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The Best Boat Rentals in Chicago
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Chicago
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,135
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$170-$1,050
Sailboats
Set sail with these traditional wind-powered boats
$125-$535
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$200-$800
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$350
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$800
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$350
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$130-$195
Kayaks
Who says you need a motor to have fun on the water?
$120
Recent Reviews in Chicago
AJ
Amy
Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
We had a great experience with Captain Z! He and the owner were very accommodating and communication was easy. The boat fit our party of 8. There was a good storage area in the cabin downstairs with a restroom on board. Coolers were provided for our food and beverages. We appreciated that fuel was included in the total cost. We enjoyed cruising around and spending time at the playpen with the beautiful Chicago skyline in the background!
DC
Daniela
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.
ZD
Zinnia
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!
Reymond
'Genius' 40' Sea Ray Sundancer Captained Charter with all amenities in Chicago!
We had an incredible July 4th charter with Danyelle! Her crew was extremely professional and made sure our group of 12—celebrating a pre-wedding event—was well taken care of. The trip included a beautiful skyline tour followed by relaxing time at the Playpen, with stunning views all around. The photos came out amazing too. Highly recommend and would absolutely book again!
Antonio
14 Passenger Captained Party & Event Boat in Chicago, Illinois!
Everything about this charter was great! The captain/crew were super friendly and the trip went off without a hitch. It rained for the first hour but the captain and crew kept everything as dry as possible and we still had an awesome trip.
RJ
Rachel
50' Multi-level Luxury Yacht with Party up to 12
Captain Jim and his team went above and beyond to make our charter an unforgettable experience. From the moment we departed to the smooth arrival back at the dock, everything was handled with professionalism, confidence, and a warm, friendly attitude. The boat was immaculate, the ride was smooth, and Captain Jim clearly knew the waters like the back of their hand. They made us feel safe, relaxed, and completely taken care of the entire time. Whether it was pointing out interesting sights, adjusting course for the best views, or making sure we had everything we needed on board, their attention to detail was exceptional. You can tell they truly love what they do—and it shows in the way they connect with guests and manage every aspect of the trip seamlessly. I highly recommend Captain Jim and his team, to anyone looking for a top-tier charter experience. Thank you again for an incredible day on the water!
How To Book on Getmyboat
Browse
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.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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Frequently Asked Questions
How much does it cost to rent a boat on Lake Michigan?
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.
How much is it to rent a yacht in Chicago?
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.
What are the best places to go boating in Chicago?
While there are many options while boating in Chicago, here is a list of the most visited boating destinations and tours in Chicago.
- Navy Pier
- Playpen
- Chicago Architecture Tour
- Cruise The River
- Shoreline Tour
When is the boating season in Chicago?
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.
What is the Playpen in Chicago?
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.
What is 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.
Does the boat rental include a captain?
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.
Why choose Getmyboat over Airbnb for Chicago boat rentals?
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.
Real reviews from happy Getmyboaters.
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