Best results for Sailing in Chicago, IL
Showing 1-17 of 17 results
Chicago Lakefront 3-Hour Sailing Cruise
Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
5.0 • 27 reviews
4-Hour Sail & Swim Charter From Navy Pier
Private Lake Michigan sailing with swimming, snacks, and a certified captain
5.0 • 27 reviews
Chicago Sunset Sailing Cruise
Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
5.0 • 27 reviews
Chicago Engagement Sailing Cruise
A private sail for proposals, photos, and a champagne toast
5.0 • 27 reviews
Chicago Sunset Skyline Sail
Sail Lake Michigan for views of Chicago’s shoreline and skyline
4.6 • 594 reviews
Chicago Blues Concert Sail
Live blues, Lake Michigan sailing, and Chicago skyline views
4.6 • 594 reviews
Chicago Sunset Skyline Sail
See Chicago’s skyline from Lake Michigan on an evening sail
4.6 • 594 reviews
Navy Pier Fireworks Cruise in Chicago
Sail Lake Michigan for Navy Pier fireworks views on a private charter
Chicago Playpen Sailing Charter
Sail Chicago's Playpen with a licensed captain and time to swim
3-Hour Sailing Charter on Chicago's Lake Michigan
Private sailboat time with Chicago skyline views
Chicago Sunset Sailing Charter
Watch the Chicago skyline glow from a private sailboat on Lake Michigan
2-Hour Sailing Lesson on Lake Michigan
Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan
Chicago Sunset Sailing Charter
A quiet private weeknight sail with Chicago skyline views
5.0 • 56 reviews
Chicago Sunset Sailing Charter
Sail Lake Michigan on a private weeknight cruise with sunset and skyline views
5.0 • 56 reviews
Cruise Chicago for Navy Pier Fireworks
Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included
5.0 • 27 reviews
Romantic Chicago Sailing Charter
Share a peaceful Lake Michigan sail with Chicago skyline views
5.0 • 56 reviews