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

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

This alley in downtown Chicago held the bodies of over 600 people after the fateful Iroquois Theatre fire.

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

A journey begins with a single step, and for many, the road-trip of a lifetime started at this Chicago intersection.

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

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

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

To find the "unicorns of the deep" you've got to go downstairs.

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

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

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

Half-sized replica of the Leaning Tower of Pisa built to honor Galileo.

A Bibliophile's Dream.

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

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

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

Former bath house turns gastropub.

One of the last functioning antique elevators in Chicago.

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

An antiquated German apothecary on Chicago's North Side.

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

Fragments of architectural wonders from around the globe are embedded in the newspaper building's walls.

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