The notorious headquarters of a corrupt political machine.

The most confusing clock in New York.

The rough and tumble president's childhood home displays the shirt he was once shot in and the speech that saved him.

Try not to get slimed in Tribeca.

Order scoops of pandan, lychee, and black sesame at this family-run institution.

The impeccably spiced roast pork buns at this bakery are worth the wait.

The façade of this building looks like a bingo board, but it's really a giant clock by a famed graphic designer.

Built hundreds of years ago this downtown iron barrier once protected a much despised king.

Manhattan’s Battery Park has a whimsical carousel full of spinning, glowing fish.

The home of the first American-born saint is one of the only curved buildings in New York.

This Wall Street bar was once a hub of revolutionary activity where Washington famously bid farewell to his troops.

Amid the bustle and noise of the Financial District hides a secluded garden oasis above the city streets.

Possible relics of the ancient Roman city are hidden in this restaurant's façade.

Alexander Milliner, a favorite of General Washington, is interred at Mt. Hope Cemetery along with 80 other Revolutionary War veterans.

The iconic Chicago sculpture hides a beautiful and easily overlooked plaque on the backside.

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.

A journey begins with a single step, and for many, the road-trip of a lifetime started at this Chicago intersection.

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

A shining sculpture made of 3,115 lights, the number of visible stars in the Northern Hemisphere.

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

Honoring the star of the “The Bob Newhart Show” which took place in the city of Chicago in the 1970s.

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

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