The last holdout of a pre-Civil War rebel who took the matter of slavery into his own hands.

Conveniently located within binocular range of a nuclear bunker, the "summer camp" area was a painfully obvious spy house.

The shelves in the back of this thrift store are devoted to saving, not selling, retro tech.

An allegorical sculpture in Maryland wears the artist’s politics on its trunk.

Walk a trail through a historic Quaker town that outlawed slavery in 1777 and was a major waypoint on the Underground Railroad.

The winding route passes through an enclosed alleyway, two tunnels, and leads to the White House basement.

The rogue roots are gradually consuming some of the historic marble grave markers.

A monument celebrating the idea of reaching inaccessible places.

Taste the white whiskey that the United States' first president once distilled and enjoyed.

This stunning blue and gold room changed cities twice before becoming part of the Smithsonian.

The original Garfield station is the oldest station facility on the "L", with the station house dating from 1892.

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

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

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

Where old school Polish Chicago and young hipster Chicago live side by side.

The palatial McDonald's that inspired Wesley Willis.

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

A giant bronze coil of feces is both a tribute to doggie defecation and a reminder to pick it up.

This historic hotel invented the chocolate brownie.

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

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

A military museum and library dedicated to the citizen soldier.

The largest retailer of seashells in the world.

The sweetest graveyard in the world is filled with headstones for dearly de-pinted ice cream flavors.