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.

A towering Art Deco movie palace made to look like a Mayan temple.

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

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

This architectural stunner is one of the few surviving Egyptian Revival theaters in the U.S.

An eccentric park and pool.

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

A historic and oft-filmed prison stands in a Chicago suburb.

Designed by Alfred Caldwel, this landscape showcases his vision of a native garden.

This memorial plaque remembers a strangely shallow maritime disaster known as "Chicago's Titanic."

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

This urban drawbridge gained eternal pop culture fame when the Blues Brothers jumped it while it was raised.

Illegal drag racing two stories beneath Chicago’s streets.

The multinational Burger King chain is banned from operating within 20 miles of a family restaurant filed under the same name.

No one knows how many bodies are in this vault in a Chicago public park.

Former bath house turns gastropub.

The 606 is a decade in the making.

Quirky water tower advertises the long-gone Brooks Tomato Products Co.

A European-style bath house in Chicago.

Rifle through images of skyscrapers, Worlds Fairs, and more in the largest public postcard repository in America.

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

This sprawling mini-golf empire is an impressive testament to a disappearing attraction.

This awkward aquarium sculpture is one of the strangest statues in Chicago.