A quiet private weeknight sail with Chicago skyline views
2 hours
Up to 6 people
Private sail, captain, water
Set sail on Lake Michigan for a private weeknight cruise away from the crowds. Take in Chicago skyline views as evening settles over the water.
Cancel or reschedule less than 72 hours before departure for a 10% fee. No refund for cancellations less than 24 hours before departure.
Product ID: 2EWBXS
Dress in layers, as it can be cooler on the water. Wear soft-soled shoes such as sneakers or boat shoes; high heels and black-soled boots are not permitted on deck.
Yes. You may bring your own snacks and beverages. A cooler with ice and bottled water is available on board.
The charter sails in light rain and varying conditions. If dangerous weather, such as high winds or lightning, requires cancellation, you will be notified about rescheduling or a refund.
We can’t say enough great things about our sailboat cruise!! Erik and Catherine were incredibly welcoming and friendly. I would recommend booking this to everyone! We will absolutely be back.
Margaret May
July 3, 2026
We can’t say enough great things about our sailboat cruise!! Erik and Catherine were incredibly welcoming and friendly. I would recommend booking this to everyone! We will absolutely be back.
Margaret May
July 3, 2026
Paddle the Chicago River past the Wild Mile and downtown skyline
Cruise Chicago by private 47 ft yacht with space for up to 12 guests
Meet Farm Animals and Native Wildlife Across Five Acres
Paddle the Chicago River and learn downtown architecture in 3 hours
Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests
Taste international dough-based treats while exploring Wynwood’s art district