Established in the '60s, a family-owned tropical drink bar founded by Ray Buhen, bartender to the stars.

An artsy hidden staircase leads to breathtaking views of San Francisco.

An unassuming store hides relics of its former life as the jazz club that hosted some of the best black performers of the 1920s and '30s.

Hot Doug's "Hot Dog" Stand.

Pizza with a side of fine art.

A century-old network of freight tunnels underneath the city's historic business district.

This historic house museum that celebrates one of the world's most influential social reformers is also one of the most haunted locations in Chicago.

Designed by Alfred Caldwel, this landscape showcases his vision of a native garden.

Honoring Italian greats from Joe DiMaggio to Rocky Marciano.

The last masonry skyscraper ever built reveals a transitional moment in architectural history.

A spectacular remnant of an Adler and Sullivan masterpiece that was destroyed in 1972.

Chicago's Navy Pier on Lake Michigan was a training hub for aircraft carrier pilots during WWII.

Huge abstract sculptures of the Puerto Rican Flag.

A 400-foot-tall tall map of Chicago makes this once-ignored building stand out.

These chunky stone towers out in Lake Michigan are the key to Chicago’s drinking water.

Partially submerged Buddha heads freckle Chicago’s neighborhoods.

This titanic Catholic church in Chicago is also a refuge of the fictional cult-favorite wizard detective Harry Dresden.

One of the few remaining relics of the meatpacking hub that made Chicago the "hog butcher to the world."

Illegal drag racing two stories beneath Chicago’s streets.

Hidden on the 7th floor of a historic building, this Cajun spot features wall-to-wall bottles of hot sauce.

No one knows how many bodies are in this vault in a Chicago public park.

Not to be confused with the iconic New York City skyscraper, this Chicago building is a vibrant hub for artists.

This landmark of the Chicago silent film industry may not be in the picture business anymore but it still stands proudly.

This urban drawbridge gained eternal pop culture fame when the Blues Brothers jumped it while it was raised.