Planes, trains, and automobiles have all been sunk as attractions at this Illinois diving spot.

An unassuming store hides relics of its former life as the jazz club that hosted some of the best black performers of the 1920s and '30s.

The history of funerals and funerary customs.

Once known as the Illinois Asylum for the Incurable Insane.

A notorious Route 66 eatery once frequented by Al Capone.

The famous author's birthplace is preserved in a town that he once described as narrow-minded.

The remains of a Rockefeller's lush Italianate estate hidden in the underbrush on the coast of Lake Michigan.

Arguably the best example of an authentic Dutch windmill in the United States, rivaling its counterparts in the Netherlands.

First known as the "Sample House," this construction mash-up was meant to be a living catalogue of building styles.

This abandoned 19th century orphanage started as a boarding school for children of Civil War veterans.

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

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

A small abandoned and abused cemetery that has become a magnet for ghost hunters.

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

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

A century-old network of freight tunnels underneath the city's historic business district.

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.

Chicago's North Park Village was once the largest municipal sanatorium in the country.

When you visit his grave, be sure to rub the Great Emancipator's nose for good luck.

A onetime gangsters' hideaway where you can dine on steaks, fine wines, and cigars just like they once did.

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

A replica viking ship from the Chicago World's Fair is still in dry dock in an Illinois park.

What may be America's largest classic video game arcade lurks inconspicuously in a Chicago suburb.