Chicago’s last original drive-in restaurant is a family-run hot dog joint that started in 1948.

Pizza with a side of fine art.

You can take a class, browse the library, or visit the lavish lair of an international men's humor society.

The unluckiest U-boat in the entire German fleet is now on display in a Chicago museum.

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

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

A historic 1929 art-house cinema that features independent, classic, cult, and foreign films in an atmospheric setting.

This old-fashioned confectionary has been family owned and operated for more than a century.

The rodent-shaped sidewalk imprint that earned worldwide media attention.

Hot Doug's "Hot Dog" Stand.

Former meatpacking facility turned vertical farm and sustainable business complex.

A lush green oasis in the middle of Chicago.

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.

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

Huge abstract sculptures of the Puerto Rican Flag.

This titanic Catholic church in Chicago is also a refuge of the fictional cult-favorite wizard detective Harry Dresden.

Former bath house turns gastropub.

One of the last functioning antique elevators in Chicago.

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

Location of the Real World's disastrous, and protested, eleventh season.

A Bibliophile's Dream.

A speakeasy takes on Chicago's drinking culture.

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

Once called the "Polish Gold Coast" it is an icon of the neighborhood that bears its same name.