Places JennyBenny Wants to Go

Sip whiskey in a powerhouse that once belonged to a storied hydroelectric dam.

In a quiet north Chicago neighborhood rests a stunning relic of the golden age of earthenware design.

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

These pretty kitties killed and ate as many as 135 railway workers.

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

Former meatpacking facility turned vertical farm and sustainable business complex.

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

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

Cemetery featuring rare glass-fronted columbarium.

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

This surprising gem is a world-class archeological museum hidden at the University of Chicago.

This $3 million model train takes you through Chicago, Seattle, and the thousands of miles in between.

The world's only known button museum.

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

An outdoor urban gallery of large-scale artworks by the world's most influential street artists.

This alley in downtown Chicago held the bodies of over 600 people after the fateful Iroquois Theatre fire.

Each of these gorgeous, intricately decorated rooms is painstakingly crafted to the scale of 1 inch: 1 foot.

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

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

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

This historic hotel invented the chocolate brownie.

Nonprofit art center that promotes outsider, intuitive, and self-taught art.

These abandoned grain silos and tunnels are an urban exploration dream.

Chicago's museum dedicated to the history of bondage and fetishism is more textbook than titillation.