Top 2 Sailing Trips in Chicago

1.Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

★★★★★★★★★★5.0 · 70 reviews · 2 hours (approx.) Our pick

Sail privately from Navy Pier for Chicago skyline views, flexible routes, Bluetooth music, and a relaxed two-hour Lake Michigan outing.

“Mike was awesome! A beautiful experience on Lake Michigan! Thank you for being a great captain! Would definitely do again.”

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2.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49Best value

Cruise Chicago’s river aboard a historic wooden yacht, with expert architecture commentary, skyline views, snacks, and a small-group feel.

“The historic information provided was interesting and informative. I recommend this tour for anyone visiting Chicago highly!”

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