The Best Boat Rentals Near Winthrop Harbor

44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available

Capt. Tim and crew were very accommodating and helpful. We rented the boat to scatter a loved ones ashes close to Navy Pier. Capt Tim was very receptive to our feelings and knew actually what we needed. We had a great celebration of life on his boat!

28ft. Sea Ray Captained Boat Rental in Chicago

Our party of 4 had a great time on Captain Memo’s boat. He was very communicative and sent a helpful video on where to find the marina. He also took pictures for us and sent them promptly following the ride. He made us feel very safe and welcomed.

27 ft Sea Ray, Captain Included

Bobby was the best captain! We left right on time and the water was beautiful. He had a cooler with ice prepared and ready for us upon arrival, and made the whole trip a time to remember! I could not recommend him enough!

Manitou 23ft Pontoon on the Milwaukee River

Ryan provided an excellent tour of the Milwaukee river. He’s very personable and informative and my crew thoroughly enjoyed themselves. I highly recommend him as a captain, we will definitely hire him the next time we’re in town.

Party Chicago Fun Lake River | 27ft Xperience Tritoon

This was an awesome boat and perfect for a small group! We were running a bit late and they were accommodating. 10/10 experience and will be booking again!

28ft. Sea Ray Captained Boat Rental in Chicago

Captain M was great!! On time, had us laughing and very personable! Boat was perfect for a relaxing day on the lake with a group of friends