Chicago · SAILING
The 4 best sailing trips you can book right now, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.
Private 2-hour sail on Lake Michigan from Navy Pier. Flex route, Bluetooth music, and Chicago skyline views for up to six.
“Captain Mike was awesome, really friendly, making the trip truly memorable. The city of Chicago is the perfect backdrop, so we absolutely recommend!”
Historic Chicago River architecture cruise on a wooden yacht. Learn landmarks, sip soda and coffee, and take photos on a 90-min ride.
“The tour guide was amazing! He spoke without notes the entire time and knew pertinent facts about buildings, the architects and even dates. He later told one of the ladies in our group that he has a photographic memory - and it is easy to believe. He also knew about pending developments along the river which was an added bonus.”
Private Lake Michigan sailing for up to four with a US Coast Guard captain, flexible route, and Chicago skyline views from Monroe Harbor.
“Great experience super relaxing and wonderful sights. Loved the privacy, I did great with my dramamine ans bracelets so no sea sickness it was a cool way to see the city.”
Private Lake Michigan yacht charter in Chicago for up to 10, with flexible 3 to 8 hour cruises, onboard restroom, and skyline views.
“We had an unforgettable water tour of Chicago! Our captain was knowledgeable, kind, and made the entire experience seamless. He shared just the right amount of history and stories about the city, while also giving us plenty of time to relax and take in the incredible skyline views. The boat itself was perfect—clean, comfortable, and well-equipped. What stood out the most was how available and accommodating he was to our group’s needs, making sure everyone felt welcome and cared for. Truly a first-class experience—I would recommend this tour to anyone visiting Chicago”
Every kind of day out in the city, and the best of each.
