Places CityBoy Wants to Go

The graveyard is filled with beautiful funerary art and boasts breathtaking views of Florence.

Over 50 exquisite hand-painted Renaissance maps decorate a Medici storage room.

Drink wine handed out through a window as part of an age-old tradition.

A subterranean world of tunnels links several buildings of this rare 19th-century asylum.

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

The original Garfield station is the oldest station facility on the "L", with the station house dating from 1892.

One of the last functioning antique elevators in Chicago.

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

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

Home to a protest movement, a bombing, and a dramatic change in labor history.

The 606 is a decade in the making.

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

A European-style bath house in Chicago.

What was once one of the country's largest confectionary plants is now an abandoned ruin, but is still pretty sweet.

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

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

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

A century-old network of freight tunnels underneath the city's historic business district.

An antiquated German apothecary on Chicago's North Side.

A haunting statue called "Eternal Silence" has quite the reputation among visitors with active imaginations.

An enormous park-like oasis, full of famous Chicagoans’ graves.

A giant bronze coil of feces is both a tribute to doggie defecation and a reminder to pick it up.

A speakeasy takes on Chicago's drinking culture.

This whimsical Oz-themed park had a wonderful impact on the surrounding neighborhood.