Chicago’s #1 Boating Experience

Captained Boat Charters

Weekend Charter
$1,600

4 hour charter Sat & Sun

Have a fun day on the lake. Visit the Playpen, Jump in the water, cruise around Navy Pier, take in unparalleled views of the city!

Up to 10 Guests*
Captain and fuel fee included (paid on the day of departure per USCG law)
Depart/return from Burnham Harbor
2 fridges and 1 cooler On Board- BYOB
Bluetooth connection
6ft x 18ft Lily Pad included

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Week Day Charter
$1,450

3 hour charter Mon-Fri

Have a fun day on the lake. Visit the Playpen, Jump in the water, cruise around Navy Pier, take in unparalleled views of the city!

Up to 10 Guests*

Captain and fuel fee included (paid on the day of departure per USCG law)
Depart/return from Burnham Harbor
2 fridges and 1 cooler On Board- BYOB
Bluetooth connection
6ft x 18ft Lily Pad included

Learn more

Chicago River Cruise
$1,750

2 hour charter

Cruise the river! Perfect for work events or a fun time with friends. Pick up and drop off at City Winery on the river!

Up to 10 Guests*
Captain and fuel fee included (paid on the day of departure per USCG law)
Depart/return from City Winery
2 fridges and 1 cooler On Board- BYOB
Cruise the river
Bluetooth connection for music

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Fireworks Cruise
$1450

2.5 hour charter

Cruise the lakefront, take in the city lights, enjoy some music and beverages as you watch the Navy Pier firework show!

Up to 10 Guests*
Captain and fuel fee included (paid on the day of departure per USCG law)
Depart/return from Burnham Harbor
2 fridges and 1 cooler On Board- BYOB
Bluetooth connection
6ft x 18ft Lily Pad included

Learn more

NEW

Chicago River Happy Hour Cruise

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NEW Chicago River Happy Hour Cruise -

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Welcome to The Chicago Captain: Your Gateway to Private Boat Charters, Chicago River Cruises, and Playpen Party Boat Rentals in Chicago.

Experience the best of Chicago's waterways with The Chicago Captain. We offer private boat rides, captained boat charters, and party boat rentals, providing you with an unforgettable adventure on Lake Michigan and the mesmerizing Chicago River.

Private Boat Charters on Lake Michigan and the Chicago River:

Enjoy the ultimate exclusivity and privacy with our private boat charters in Chicago. Whether you're seeking a romantic outing, a family gathering, or a corporate event, our captained boat charters are the perfect choice. Explore the breathtaking beauty of Lake Michigan or the Chicago river, taking in the iconic Chicago skyline from a unique vantage point. Our experienced captain will guide you to the most scenic spots, ensuring you capture remarkable moments and create lasting memories.

Dance to your favorite music, socialize on the spacious deck, and enjoy the stunning views as you cruise tha lake, explore the river, or party in the Playpen. Our boat is equipped with state-of-the-art sound systems and comfortable seating areas to create the perfect atmosphere for your party.

Why Choose The Chicago Captain?

Versatile Experiences: Whether you're seeking a private boat ride on the lake or the river, we offer a range of experiences to suit your preferences.
Experienced Captains: Our highly professional captains have extensive knowledge of the Chicago waterways and will ensure your safety and enjoyment throughout your journey.
Stunning Views: Capture breathtaking views of Chicago's skyline, architectural wonders, and natural beauty from the comfort of our boat.
Customizable Packages: We understand that every occasion is unique. Our team is dedicated to creating personalized packages that cater to your specific needs, ensuring a memorable experience for you and your guests.

Contact us today to reserve your spot and experience the best of Chicago from the water. The Chicago Captain is your go-to choice for exceptional boat charters in the Windy City.

Tables and bimini top can be put up as needed.

Great layout for large groups of people.

There is a sink and fridge, as well as a cooler on board.

Downstairs cabin. Perfect for changing clothes and storing your bags.

Fully enclosed bathroom downstairs in the cabin for privacy.

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Our Customers Love Us!

Captain Paul Is a Fan Favorite and We Always Go The Extra Mile To Show You a Great Time On The Water!

Check Out Our Google Reviews!!

"I am so glad I booked a boat with The Chicago Captain for my bachelorette party. I called and emailed a few times with questions and they were so responsive. On the day of, Captain Paul texted me and made getting on the boat so easy. He was a blast to have as a captain and even brought out his guitar to sing to us. My girls and I could not have asked for a better day. Thank you Chicago Captain and Captain Paul!"

Mia Simone
August 2022
"Captain Paul could not have made our our boat day better! He showed us major landmarks, shared amazing history, took us to the playpen and even sang some songs on the guitar. Truly a memorable day and will definitely be booking again!!!"

Juliette Eiseman
August 2022
“Captain Paul is the best! He’s friendly, knowledgeable, and makes everyone feel at ease right away. The boat is clean and comfortable, and we had the best time relaxing, floating on the lily pad in the lake, and taking in amazing views of Chicago. Can’t recommend him enough!”

Sam Thompson
September 2022
“I highly recommend this charter! I came with a group of 8 colleagues to watch the Wednesday fireworks and it was truly an amazing experience. Trevor was very accommodating and a great host. Everybody had so much fun listening to music, eating dinner, and hanging out while enjoying the view. Thank you Trevor!!”

Anneke Lanou
July 2022
"Paul was an amazing captain and ensured that my friends and I had a great time. He also was very knowledgeable about the city and waterways. I would definitely recommend this company."

Dan Jeter
June 2022
"It’s a PARTYYYY with the Chicago Captain!! What a great time :)"

Anthony Sullivan Jr.
August 2022
"Captain Paul was the best - what a fun day in the sun in the playpen. He gave us the dish on some Chicago landmarks, played us some tunes and helped keep the vibes sky high. The best time !!! Run, don't walk, people !!!"

Laura Hollo
July 2022
"Super easy to book, the boat is awesome, and Captain Paul is a world-class seafarer. My friends and I had a really fun time and we'd love to book with them again."

Dan Sabella
June 2022
"We had an excellent time, our captain (thechicagocaptain) was very accommodating and kind! We had the best time and it was easily the highlight of out weekend."

Parna Saha
September 2022
"Amazing experience. Trevor was accommodating, friendly, and the boat was great. Def recommend."

Benjamin Mahoney
July 2022