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

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

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

The last remnants of a lakeside airport that was bulldozed overnight by the mayor of Chicago.

Kwanu'sila the Thunderbird has been silently watching over Chicago for more than 100 years (kind of).

A long lost multi-cultural music venue used to reside in the bottom floor of Chicago's Flat Iron Building.

Parking lot where a Chicago mayor was inaugurated under very sketchy circumstances.

Landmark Chicago building narrowly avoided destruction.

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

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

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.

Huge abstract sculptures of the Puerto Rican Flag.

The last masonry skyscraper ever built reveals a transitional moment in architectural history.

A spectacular remnant of an Adler and Sullivan masterpiece that was destroyed in 1972.

These chunky stone towers out in Lake Michigan are the key to Chicago’s drinking water.

Once at the center of U.S. finance, the historic Trading Room was meticulously recreated piece by piece and rebuilt in the Art Institute.

Theater has had many different incarnations but has survived the ravages of time.

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

A 400-foot-tall tall map of Chicago makes this once-ignored building stand out.

This historic house museum that celebrates one of the world's most influential social reformers is also one of the most haunted locations in Chicago.

One of the few remaining relics of the meatpacking hub that made Chicago the "hog butcher to the world."

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

Not to be confused with the iconic New York City skyscraper, this Chicago building is a vibrant hub for artists.

Illegal drag racing two stories beneath Chicago’s streets.