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

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

Partially submerged Buddha heads freckle Chicago’s neighborhoods.

Huge abstract sculptures of the Puerto Rican Flag.

A towering Art Deco movie palace made to look like a Mayan temple.

Roses and other fascinating flora fill this garden built to commemorate Britain's immortal Bard.

It was originally part of a "terrible lizards" collection at the 1964 New York World’s Fair.

A historic beacon built in the aftermath of the worst maritime disaster on the Great Lakes.

Once at the center of U.S. finance, the historic Trading Room was meticulously recreated piece by piece and rebuilt in the Art Institute.

The oldest house in Chicago certainly doesn't look the part and there are some who say it doesn't deserve its title either.

Illegal drag racing two stories beneath Chicago’s streets.

This surprising gem is a world-class archeological museum hidden at the University of Chicago.

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

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

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

Former bath house turns gastropub.

The final resting place of up to 6,000 Confederate soldiers, the largest mass grave in the Western Hemisphere.

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

This sprawling mini-golf empire is an impressive testament to a disappearing attraction.

An avant garde art museum at the University of Chicago.

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

Recognized the world over as the home of the McCallisters in the 1990 movie "Home Alone."

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

Former meatpacking facility turned vertical farm and sustainable business complex.