An avant garde art museum at the University of Chicago.

A beloved Chicago music venue offering cold beer and lots of “Friendly."

One-of-a-kind preserved ruins of an abandoned 1880s church in Chicago's Pilsen neighborhood.

One of the largest pieces of scientific equipment ever carried on a NASA space shuttle sits in a Chicago alley.

First planned industrial community in the United States.

A little-known subterranean street runs under some of the best-known buildings in Chicago's River North.

Combination beer garden and music venue in the heart of Wicker Park.

Former meatpacking facility turned vertical farm and sustainable business complex.

Beloved bar home to musicians of all eras and reputations.

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

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

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

This historic hotel invented the chocolate brownie.

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

Internationally known record store and purveyor of "dusties."

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

A century-old hotspot for jazz, frequented by everyone from Charlie Chaplin to Al Capone.

This unauthorized stone mermaid was secretly carved out of public stone before being permanently preserved.

An antiquated German apothecary on Chicago's North Side.

A Bibliophile's Dream.

A speakeasy takes on Chicago's drinking culture.

This morbid, delightful curiosity shop offers everything from animal bones to human teeth.

"World's largest scrap metal sculpture" stands in an outdoor sculpture garden in the middle of Wisconsin.

According to local lore, this narrow passageway through two large rocks was accidentally created by the devil himself.