Sailing


CHICAGO · ILLINOIS

Best Sailing Tours In Chicago

The best of Chicago.

The 2 best sailing tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.

2 Best Sailing Tours In Chicago

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago - Navy Pier and the Grand Ballroom View: Chicago’s Waterfront Icebreaker
Chicago, Cruises & Boat Tours, Lake Michigan Cruises, Private, Sailing, Tour Reviews

Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

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

Private sailing on Lake Michigan from Navy Pier lets you cruise past Chicago’s icons in a flexible 2-hour charter for up to six.

Most Popular★ 5.0

“Wonderful day out on the water! Visited Chicago many times before, but first time out on Lake Michigan. Will be making this a tradition every time I visit during warmer months!”

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Chicago River Architecture Tour Aboard a Historic Yacht - Meeting at 465 N McClurg Ct: easy to find, close to the action
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Historical Tours, Sailing, Tour Reviews, Tours

Chicago River Architecture Tour Aboard a Historic Yacht

2.Chicago River Architecture Tour Aboard a Historic Yacht

Ride a historic yacht on the Chicago River for a 90-minute architecture tour past Wrigley Building, the Riverwalk, and bridges. $49.

★ 5.0

“As someone else mentioned- guide is very knowledgeable. However, the narration is non-stop, too fast, and too loud. Nice to have a small boat- versus the very large ones. Bring sunscreen, hat, etc. the sun can be brutal. Bring smaller- it’s more handicap accessible to bRead more”

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