Live stand-up, touring comedians, and skyline views aboard a historic fireboat
Share a peaceful Lake Michigan sail with Chicago skyline views
A quiet private weeknight sail with Chicago skyline views
Sail Lake Michigan on a private weeknight cruise with sunset and skyline views
Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water
Private Lake Michigan fishing with an expert crew
Cruise Chicago’s lakefront for skyline and Navy Pier views
Cruise about two miles offshore for wide-open Chicago sunset views
Speed across Lake Michigan with your own music and skyline views
Cruise offshore from Navy Pier for fireworks and skyline views
Cruise Chicago’s waterfront with a professional crew and private gathering spaces
Celebrate on the Gypsy Spirit along Chicago’s waterfront
Look beyond the brickwork to uncover a neighborhood's surprising stories
Discover the many lives of Wicker Park through its bricks and buildings
Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
Private Lake Michigan sailing with swimming, snacks, and a certified captain
Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
A private sail for proposals, photos, and a champagne toast
Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included
See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft
Trace Chicago's skyscraper story with a donut tasting
Step inside Chicago Loop landmarks and trace the evolution of its skyline
Private skyline cruise with a local perspective