Street Shenanigans
Neighborhood Nonsense
Suburb Shenanigans
Famous Foolery
Train Trouble
100

These two streets got their names from being the former northern and western boundaries of the city, respectively. 

What are North Avenue and Western Avenue?

100

Bounded by the Chicago River to the north and the South Branch Chicago River to the west, Chicago's main downtown area.

What is The Loop?

100

Now named after the Chicago Portage of the DesPlaines and Chicago rivers, this suburb was originally named after a corn starch factory.

What is Summit?

100

Formerly the tallest building in the world, this iconic skyscraper was formerly named the Sears Tower.

What is the Willis Tower?

100

This line is famous for being the only train to connect two baseball statiums.

What is the Red Line?

200

Far western street named after the Polish American Revolutionary War hero who famously saved George Washington's life.

What is Pulaski Road?

200

This large neighborhood borders the suburb of Burbank along Cicero Avenue, and contains the famous Vito & Nick's Pizza.

What is Ashburn?

(Begrudgingly accept Scottsdale) 

200

Containing the subdivisions of Little Palestine and Southfield, this suburb's name was chosen with a singular vote over 'Oketo.'

What is Bridgeview?

200

While Chicago has no definitive 'main street,' this stretch of road north of the Chicago River is often considered it for its iconic architecture and fancy shops and restaurants. 

What is the Magnificent Mile?

200

This train has no unique stations within Chicago's city limits, using the Brown Line tracks until Belmont, where it switches to the Red Line tracks.

What is the Purple Line?

300

Formerly 12th Street, this near-south road runs from Lake Shore Drive 33 miles west to Geneva, and is named after the first of two Presidents with the same name.

What is Roosevelt Road?

300

Formerly Cemetery Park and Lake Park, this affluent neighborhood is now named after an assassinated figure commonly associated with Illinois.

What is Lincoln Park?

300

This boring suburb contains the suburban equivalent of the projects called 'The Trace,' and has one of the single stupidest names for a place ever.

What is Justice?

300

This iconic tourist attraction was originally a military training facility as well as a shipping facility, but underwent a drastic overhaul in 1995.

What is Navy Pier?

300

This line is both the most recently built and the least used, serving the lower west side.

What is the Pink Line?

400

This diagonal street runs over a former Native American trail, and is named after the first commissioner of the canal it runs along.

What is Archer Avenue?

400

Shaped similarly to Florida, this west side neighborhood is the third largest and third most populated, and has one of the highest homicide rates in the city. I also played baseball here once.

What is Austin?

400

This suburb is the birthplace of a soldier who captured Saddam Hussein, and is also the site of a certain incident involving a car of teenagers and a suspicious oak tree.

What is Hickory Hills?

400

Although it currently has no official name, the skyscraper 875 N Michigan Avenue will always be known as this name by locals.

What is the Hancock Building?

400

This by far the shortest CTA train, with a grand total of three stops, nicknamed the "Skokie Swift."

What is the Yellow Line?

500

This street was named after a former Chicago Mayor who was killed during an assassination attempt of President FDR.

What is Cermak Road?

500

This northwest neighborhood was ranked 16th on a recent list of the 'coolest neighborhoods in the world.' Also where we had Javier's birthday party.

What is Avondale?

500

In the 1960s, an F4 tornado ripped through this suburb, killing over 30 people and cutting its eponymous high school "in half."

What is Oak Lawn?

500

What was once a private landing strip has now been reclaimed into this nature park that protrudes into Lake Michigan.

What is Northerly Island Park?

500

Similarly to the Green Line, this train has an alternate route, although instead of diverging, it terminates early.

What is the Blue Line?