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

These pretty kitties killed and ate as many as 135 railway workers.

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

The twin towers in this Chicago fountain use 50 foot tall video screens to spit on people.

Each of these gorgeous, intricately decorated rooms is painstakingly crafted to the scale of 1 inch: 1 foot.

This historic hotel invented the chocolate brownie.

The sign to a demolished amusement park now stands in front of a local library.

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

Chicago’s incendiary role in the labor movement.

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.

Former bath house turns gastropub.

Beloved bar home to musicians of all eras and reputations.

Huge abstract sculptures of the Puerto Rican Flag.

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

A theater sits abandoned on Roosevelt Road, once majestic in splendor, now majestic in decay.

A lush green oasis in the middle of Chicago.

The oldest certified bowling alley in the United States is in the basement of this century-old bar.

What appears to be a wizard's lair in Milwaukee actually houses a massive water pipe.

A house and yard adorned with bizarre concrete sculptures in a Milwaukee suburb.

A 90-foot-tall psychedelic "tree" on the side of the highway has baffled passersby for decades.

The fifth-longest natural arch in the world, and the longest outside China.

This quiet park's strange sedimentary spires were named after Kodak's color film.

Come for the speed, leave in love with the desert.