El-evated Knowledge
Iconic Eats
Chi-Town Celebs
Windy City History
Happening Highlights
100

What CTA train line serves both MLB stadiums?

What is the red line?

100

Chicago food enthusiasts will gawk at anyone who chooses to eat a hot-dog with this controversial condiment.

What is Ketchup?

100

First-rate in terms of alumni, this Chicago improv group served as a career springboard for Steve Carell, Tina Fey, Amy Poehler, Mike Myers and many more famous comedic actors.

What is Second City?

100

Affectionately nicknamed "The Bean," this public sculpture designed by Anish Kapoor, completed in 2006 and is housed in Millennium Park.

What is Cloud Gate?

100

Chicago has hosted this noteable political event 25 times! 

What is the DNC/RNC?

200

What is the busiest train stop in the entire CTA system?

What is Lake/State and Lake?

200

These 2 flavors of popcorn combine to make the surprisingly delicious “Chicago Mix.” Find them at Garrett’s or Nuts on Clark!

What are caramel and cheese?

200

Look under your chair, this daytime talk show filmed in Harpo Studios in West Loop was the highest-rated in American TV history, airing for 25 seasons.

What is the Oprah Winfrey Show?

200

Don't have a cow, Mrs. O'Leary! We know those were just rumors about what sparked this 1871 Chicago disaster.

What is the Chicago Fire?

200

Who is the current mayor of the vibrant city known for its deep-dish pizza, the iconic Willis Tower, and the bustling Navy Pier?

Who is Mayor Brandon Johnson?

300

What months are the heat lamps available at all CTA rail stations? 

What is November 1st-March 31st?

300

This infamously bitter liqueur was introduced in Chicago the 1930s. Nearly a century later, there is still not much demand outside of Chicagoland for the drink which has been described as “grapefruit and gasoline.”

What is Malort?

300

This 2003 best-seller simultaneously follows dual plot lines of the architecture of the 1893 World's Fair and the murderous rampage of serial killer Dr. H. H. Holmes.

What is The Devil in the White City?

300

Considered one of the greatest feats of modern engineering, the 1900 reversal of the Chicago river sent polluted water to the Mississippi River, instead of flowing to this great natural source of drinking.

What is Lake Michigan?

300

This popular Chicago festival, known for its German holiday market, unveiled its 2024 mug design featuring a boot shape.

What is Christkindlmarket?

400

What is the only CTA rail line to not run through the Loop L?

What is the Yellow Line/Skokie Swift?

400

The history of this classic Chicago sausage sandwich begins on Maxell Street in Bridgeport, a long way from Warsaw.

What is a polish / polish sausage?

400

If you think this Chicago-set dramady is good, you should try Mr. Beef – the real italian beef restaurant this FX series is based on.

What is The Bear?

400

This president calls his time as a South Side Chicago community organizer "the best education" he ever had. Maybe this is where he learned "Yes we can!"

Who is Barack Obama?

400

This Chicago-born artist won the Grammy for Best New Artist in 2023, known for their hit single “Industry Baby

Who is Lil Nas X?

500

What CTA rail line is the oldest?

What is the green line?

500

Over the last 20+ years, a local “guy” has become a legend, carrying his signature red cooler packed with these delicious Mexican snacks for sale. “Pork, Chicken and Cheese, and Jefe!”  

What are Tamales?

500

This NBA legend led the Chicago Bulls to dynasty status, coaching personalities like Michael Jordan, Scotty Pippen, and Dennis Rodman as the bulls won 6 championships in 7 seasons.

Who is Phil Jackson?

500

In the later half of 19th Century, the perfection of the refrigerated railcar helped the Chicago Union Stockyards become the epicenter of this industry, later written about in Upton Sinclair's The Jungle.

What is Meatpacking?

500

This Chicago-born artist released their critically acclaimed album “The Windy City” in 2023, which topped the Billboard 200 chart.

Who is Chance the Rapper?

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