Places Michael Woodruff Wants to Go

JFK's assassin rented a room in the boarding house in the weeks leading up to the 1963 shooting.

Known as one of America's most beautiful public restrooms.

An off-the-beaten-path place to literally hang beneath Milwaukee's Holton Street Bridge.

A trailblazing sovereign nation tucked in the American state of Wisconsin.

A wonderfully curated used bookstore in an airport.

A group of artists transformed this desolate city alleyway into an outdoor gallery of street art.

Statue dedicated to the star of an old television show.

The bugs crawling down the front of this office building are almost as big as a '68 VW Beetle.

Once a speakeasy operated by Al Capone, this Milwaukee cigar bar is now a haven for ghost hunters.

This striking art museum holds an amazing series of curiosity cabinets.

A giant, Gilded Age mansion that once belonged to the beer baron of Milwaukee.

A place to eat for on-the-run agents and espionage enthusiasts.

A unique botanical garden housed in three giant geodesic domes.

Robots, lasers, and whoopee cushions, oh my!

Also known as the Osaka Garden, this garden was originally built in 1893 as part of the World's Columbian Exposition.

The last remaining vestige of a popular 1999 public art display.

A hidden oasis just north of Chicago's Chinatown.

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

Huge abstract sculptures of the Puerto Rican Flag.

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

This art gallery and oddities boutique bewitches visitors with a trove of occult trinkets and eccentric antiques, work by an ever-changing roster of underground artists, and classes in tarot and other mystic arts.

No one knows how many bodies are in this vault in a Chicago public park.

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

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