Chicago River Cruise
Ready for the ultimate happy hour?
Enjoy an evening on the river with friends, family, or coworkers. We have the boat, cooler, and ice ready to go! All you need to do is bring your crew and grab some booze.
Chicago River Happy Hour Cruise
Meet the boat at City Winery on the river where you and your guests will board. Cruise down the river while listening to music and sipping on a beverage. The captain will take care of everything, you just relax and enjoy your time on the water. At the end of your cruise you will get dropped off at the CIty Winery dock.
10 guests
2 Hour Charter
Available Monday through Friday
Choose your departure time. 11am, 1:30pm, 4pm, 7pm.
2 hour cruise
Captain and fuel fee included (paid on the day of departure per USCG law)
Depart/return from City Winery on the River
1 fridge and 1 cooler on board- BYOB
Bluetooth connection
Fully enclosed bathroom on board
Full refund if canceled due to severe weather or unsafe lake conditions
$1750 Total - Includes all fees and taxes. You pay $1000 deposit at time of booking and the balance the day of your chartrer.
Details: After completing your booking you will recieve a detailed email with all the information you need for your charter. A captain will be arranged for you and will be in direct communication with you the day of your charter. Your group meets at City Winery on the river and boards the boat. You will cruise the east and south branch of the river and get dropped back off at City Winery.
The Boat at City Winery.
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!
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"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
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"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
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“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
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“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
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"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
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"It’s a PARTYYYY with the Chicago Captain!! What a great time :)"
Anthony Sullivan Jr.
August 2022
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"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
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"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
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"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
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"Amazing experience. Trevor was accommodating, friendly, and the boat was great. Def recommend."
Benjamin Mahoney
July 2022