This museum celebrating the almighty dollar lets visitors literally stand in the shadow of a million bucks.

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

All of Chicago's wood-paved streets are long gone but two alleys remain.

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

Shop of curiosities with a dinosaur museum tucked in its basement.

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

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

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

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

The original vault that held the president's remains still stands, empty, not far from where he was finally buried.

This tiny historic jail along Route 66 is the perfect fit for exactly one criminal and their partner-in-crime.

This softly rounded mansion was built without corners not to avoid evil spirits, but to make them more comfortable.

More than 8,000 drinking jugs say “Cheers!” to a guy named Toby.

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

A plaque marks a former safe house on the secret route, now hidden next to a McDonald's.

The mysterious white squirrels of this Illinois city are treated like sacred cows.

This historic hotel invented the chocolate brownie.

The site of the first couple's first kiss is commemorated by the most adorable presidential monument ever.

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

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

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

A monument to the art of slicing people open.

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