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

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

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

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

This landmark of the Chicago silent film industry may not be in the picture business anymore but it still stands proudly.

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

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

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

Combination beer garden and music venue in the heart of Wicker Park.

An outdoor urban gallery of large-scale artworks by the world's most influential street artists.

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

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

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

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

What's left of the ruins of the 1893 Columbian Exhibition, or World's Fair, also known as the White City.

Internationally known record store and purveyor of "dusties."

This historic hotel invented the chocolate brownie.

An antiquated German apothecary on Chicago's North Side.

A Bibliophile's Dream.

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

A lush green oasis in the middle of Chicago.

A giant bronze coil of feces is both a tribute to doggie defecation and a reminder to pick it up.

This shop for all your super spy needs hides an educational secret.

This morbid, delightful curiosity shop offers everything from animal bones to human teeth.