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

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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: Private Boat Charters, Chicago River Cruises, and Playpen Party Boat Rentals in Chicago.

Experience the best Chicago has to offer with The Chicago Captain. We offer private captained boat charters, providing you with an unforgettable adventure on the water.

We offer Private Boat Charters on Lake Michigan and on the Chicago River:

Make our boat your own for a day and enjoy a luxurious experience with a fun and experienced captain.

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 take in the sight along the Chicago river.

Our experienced captain will guide you to the most scenic spots, ensuring you capture remarkable moments and create lasting memories.

Our boat is equipped with a state-of-the-art sound system and a comfortable seating area to create the perfect atmosphere for your party. With regridgerators on board and a private bathroom your group can enjoy the water in comfort.

Why Choose The Chicago Captain?

Versatile Experiences: Whether you're seeking a private boat ride on the lake or the river with friends and family, or a unique way to entertain clients or reward team members, we offer a range of experiences to suit your needs.
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.