Huge abstract sculptures of the Puerto Rican Flag.

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

G.V. Black, the Father of Modern Dentistry, keeps an eternal eye on Chicagoan’s teeth from his perch in Lincoln Park.

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

This memorial plaque remembers a strangely shallow maritime disaster known as "Chicago's Titanic."

This urban drawbridge gained eternal pop culture fame when the Blues Brothers jumped it while it was raised.

This historic-shipwreck-cum-diving-spot can still be seen poking its boiler out of the Lake Michigan waters that claimed it.

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

Former bath house turns gastropub.

A military museum and library dedicated to the citizen soldier.

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

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

The palatial McDonald's that inspired Wesley Willis.

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

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

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

Chicago's largest cemetery is full of beautiful Victorian monuments and more than a few ghost stories.

Beloved bar home to musicians of all eras and reputations.

Home to a protest movement, a bombing, and a dramatic change in labor history.

A display of magnificent stained glass windows is the first exhibit of its kind.

First planned industrial community in the United States.

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

This historic hotel invented the chocolate brownie.

A little-known subterranean street runs under some of the best-known buildings in Chicago's River North.