Speed across Lake Michigan with your own music and skyline views
1+ Hours
Speedboat ride, sound system
Climb aboard a Baja 27’ Boss speedboat and ride fast across Lake Michigan alongside Chicago’s skyline. Play your playlist on the onboard sound system as you take sharp turns and pass views near Navy Pier.
Total amount due upon agreement of boat ride. Refundable with five day notice. If scheduled service is less than five days, there is a $150 cancellation fee.
Product ID: 62H3S9
Plan to arrive at least 15 minutes early. The area is very congested, and the extra time helps you meet up and leave on schedule.
Look for the listing under "Chicago Blue Water Charters" on Google Maps. From the street, walk east through the Diversey Harbor parking lot to C-dock.
Yes. The boat has a state-of-the-art sound system that supports your playlists, Sirius radio, or an iPod.
2759 North Lake Shore Drive West Chicago, IL US 60614
Captain Bob has earned a near-perfect reputation on Lake Michigan, and it's easy to see why. Reviewers consistently praise his deep knowledge of Chicago's waterways, his engaging storytelling, and the relaxed, welcoming atmosphere he creates on board. His boat is frequently described as spotless, comfortable, and impressively well-maintained, with one guest comparing it to "a Porsche on water." What stands out beyond the boat itself is how personally invested Captain Bob seems in every outing. He tailors experiences to his guests, whether that means finding the best spots for the Air and Water Show or navigating to scenic sunset views. He's praised for being safety-conscious and skilled on busy waters, which clearly puts first-timers at ease. Repeat bookings and "can't wait to go back" comments show up throughout the reviews, which is about as strong an endorsement as you can get.
My wife and I had the pleasure of being on Captain’s Bob charter last weekend for the sunset cruise for our first anniversary. It was an awesome ride, full of fun and we even got to jam out to your own music. Captain Bob was very professional and gave an informative tour of the lake during the experience. Overall I would recommend this charter to whoever is looking for a great time on Lake Michigan. Thanks again Captain Bob
Anthony Sanchez-Ayra
July 13, 2026
My wife and I had the pleasure of being on Captain’s Bob charter last weekend for the sunset cruise for our first anniversary. It was an awesome ride, full of fun and we even got to jam out to your own music. Captain Bob was very professional and gave an informative tour of the lake during the experience. Overall I would recommend this charter to whoever is looking for a great time on Lake Michigan. Thanks again Captain Bob
Anthony Sanchez-Ayra
July 13, 2026
Cruise the Chicago River for 2 hours on a private, self-drive pontoon
Meet Farm Animals and Native Wildlife Across Five Acres
Paddle the Chicago River and learn downtown architecture in 3 hours
Cruise Chicago by private 47 ft yacht with space for up to 12 guests
Paddle Chicago's lakefront with skyline views and basic instruction
Taste international dough-based treats while exploring Wynwood’s art district