These mansions date back to Chicago's days as a brewer's paradise.

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

Cemetery featuring rare glass-fronted columbarium.

This awkward aquarium sculpture is one of the strangest statues in Chicago.

This historic hotel invented the chocolate brownie.

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

A hollow cement depiction of time's inexorable effect on the human body.

A 400-foot-tall tall map of Chicago makes this once-ignored building stand out.

A one-armed veteran of the Battle of Waterloo lies in a cemetery for one in the middle of a Chicago scrapyard.

One of the few remaining relics of the meatpacking hub that made Chicago the "hog butcher to the world."

This bronze sculpture on a former squash court marks the secret origins of the Atomic Age.

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

You can take a class, browse the library, or visit the lavish lair of an international men's humor society.

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

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

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

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

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

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

A gothic church spire sits atop this skyscraper, the tallest church in the world.

This quirky local sculpture is quite literally a fish out of water.

The final resting place of one of the most iconic musicians of the '80s.

A monument to a Native American leader who was known for never breaking a promise and met his end after signing a deal with white settlers.

This massive airship factory is so large that it has its own indoor weather.