400 million-year old limestone caverns nestled in the Ozarks served as shelter and a hideout for cultures throughout North American history.

St. Augustine's record-setting narrow street was designed to protect against pirates.

"We Seceded Where Others Failed."

A monument celebrating the idea of reaching inaccessible places.

A luxurious 1880s hotel with its fair share of Tiffany stained glass, Edison electricity, and of course, ghosts.

Island ghost town detailing Flagler's folly in building the Overseas Railroad.

A tribute to Ponce de Leon's supposed quest for eternal youth.

Hot Doug's "Hot Dog" Stand.

Illegal drag racing two stories beneath Chicago’s streets.

Landmark Chicago building narrowly avoided destruction.

Location of the Real World's disastrous, and protested, eleventh season.

Huge abstract sculptures of the Puerto Rican Flag.

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

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

Once called the "Polish Gold Coast" it is an icon of the neighborhood that bears its same name.

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

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

The palatial McDonald's that inspired Wesley Willis.

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

Pizza with a side of fine art.

A lush green oasis in the middle of Chicago.

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

An antiquated German apothecary on Chicago's North Side.

This massive stained-glass masterpiece is thought to be the largest Tiffany dome in existence.