This modest post office sits on the site of H.H. Holmes' famous murder castle.

The unluckiest U-boat in the entire German fleet is now on display in a Chicago museum.

This $3 million model train takes you through Chicago, Seattle, and the thousands of miles in between.

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

A haunting statue called "Eternal Silence" has quite the reputation among visitors with active imaginations.

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

A strange rock in Chicago marks the spot where a tree once stood in honor of the 18th President.

Hot Doug's "Hot Dog" Stand.

A lush green oasis in the middle of Chicago.

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

Huge abstract sculptures of the Puerto Rican Flag.

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

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

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

A Bibliophile's Dream.

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

The beloved home to all publications indie, erotic, and punky.

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

Where Cusack's record store from the film "High Fidelity" was located.

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

Beloved bar home to musicians of all eras and reputations.

A Japanese temple, old German townhouses, and public chess tables offer a peaceful escape from the bustle of the North Side.

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

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