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!”

Check Availability →Read the review →

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”

Check Availability →Read the review →

Scroll to Top

Explore Chicago

From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.