Best results for Chicago Illinois

Charter a private 38' yacht on Lake Michigan for up to 13 guests

Cruise and swim aboard a spacious Sea Ray with room to lounge

Eat a donut, then head up to the Willis Tower Skydeck

Walk the Chicago Loop to see hidden interiors and Millennium Park

Cruise the Chicago River on a private boat with local architecture stories

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft

Fly over Chicago landmarks with a private helicopter for up to 3

Take the controls in a 30-minute helicopter intro flight

Step inside Chicago’s Art Deco buildings on a 2-hour Loop walk

Watch fireworks and Chicago sights from a floating tiki bar

Watch Chicago fireworks from a floating tiki bar with a full onboard bar

Walk downtown Las Vegas and sample donuts and churros in 2 hours

Taste your way through downtown Boston on a private donut walk

Parasail up to 500 feet above Lake Michigan for skyline views

Discover Chicago architecture and fireboat history on a guided river cruise.

Live Electric Brew jams aboard a historic Chicago fireboat

Live stand-up, touring comedians, and skyline views aboard a historic fireboat

Eat Chicago favorites as you walk past top landmarks with a guide

Explore Chicago with other solo travelers on a guided social adventure

Bike and taste your way through Miami Beach’s Art Deco streets and local eats

Taste four Chicago pizza styles on a guided West Loop walk

Visit four Chicago pizzerias and compare four pizza styles by bus

Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way