A century-old hotspot for jazz, frequented by everyone from Charlie Chaplin to Al Capone.

A gothic church spire sits atop this skyscraper, the tallest church in the world.

A lush green oasis in the middle of Chicago.

An antiquated German apothecary on Chicago's North Side.

Four glass boxes hover over 1,000 feet in the air to give visitors an unparalleled view of Chicago.

Illegal drag racing two stories beneath Chicago’s streets.

A little-known subterranean street runs under some of the best-known buildings in Chicago's River North.

Home to a protest movement, a bombing, and a dramatic change in labor history.

A strange and haunting monument of unknown origin in the historic Graceland Cemetery.

An enormous park-like oasis, full of famous Chicagoans' graves.

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

A hot dog stand where the heads are just as hot as the dogs.

An eccentric park and pool.

The world's only known button museum.

Landmark Chicago building narrowly avoided destruction.

This whimsical Oz-themed park had a wonderful impact on the surrounding neighborhood.

The subtle science of a master molecular gastronomist.

Built to house a chapter of the Knights Templar, this grandiose building is a relic of Freemasonry in Chicago a century ago.

A beloved Chicago music venue offering cold beer and lots of “Friendly."

Internationally known record store and purveyor of "dusties."

Theater has had many different incarnations but has survived the ravages of time.

Odd, decrepit fountain honors Chicago author who had mixed feelings about his hometown.

Orthodox church partially financed by Tsar Nicolas II.

Huge abstract sculptures of the Puerto Rican Flag.