Chicago History
Chicago Flag
Chicago Food
Chicago Sports
Miscellaneous
100

What year was The Great Chicago Fire?

1871

100

How many stars are on the Chicago Flag?

4

100

What are the two foods most commonly labeled "Chicago style"? 

The Chicago-style hot dog and Chicago-style deep dish pizza.

100

What animal supposedly kept the Cubs from reaching the World Series for 71 years?

A goat. The curse of the Billy Goat lasted 71 years, from 1945 to 2016.

100

Who is Chicago's current mayor?

Mayor Lori Lightfoot

200

What building stands as a memorial to the Great Chicago Fire to this day?

The Old Water Tower

200

What are the three colors on the Chicago flag?

baby blue, red, and white

200

What two flavors make up Garrett's Chicago Mix popcorn?

Caramel and cheese 

200

How many Stanley Cup championships have the Blackhawks won?

Six since their founding in 1926: 1934, 1938, 1961, 2010, 2013, 2015.

200

What historic interstate route started in Chicago and went all the way to California?

Route 66. It started in Grant Park, on Adams in front of the Art Institute, and ran 2,448 miles cross-country to Santa Monica.

300

What percentage of Chicago residents were left homeless after the fire (within 5%)?

28%

300

What do the two blue lines on the Chicago flag represent?

Lake Michigan and Chicago River

300

What Greek food, born in Chicago, is served flaming tableside while the servers cry "OPA"? 

Flaming saganaki

300

What was the Bears' original team name?

The Decatur Staleys

300

What is the longest road in Chicago?

Western Avenue 

(23.5 miles from Howard to 119th)

400

A reported 844 people were drowned on this boat disaster in 1915.

The Eastland tragedy. The largest loss of life from a single shipwreck on the Great Lakes.

400

What does the 2nd star on the Chicago flag represent?

The Great Chicago Fire. The others are Fort Dearborn, the World's Columbian Exposition of 1893, and the Century of Progress Exposition of 1933–34.

400

What Chicago-born sandwich is inspired by the culinary traditions of Puerto Rico?

The Jibarito: meat — usually steak — with garlicky mayonnaise, fresh tomato slices, lettuce, onions and cheese between slices of fried plantain.

400

How many championships did the Bulls win in the 1990s?

Six: 1991, 1992, 1993, 1996, 1997, 1998. 

400
How many distinct neighborhoods / communities are in Chicago?

77

500

Who is considered the first non-indigenous permanent resident in Chicago?

Jean Baptiste Point du Sable, honored as "the founder of Chicago."

500

Who designed the Chicago flag?

Wallace Rice

500
At what Chicago event was the brownie created?
At the 1893 World's Fair, by the Palmer House pastry chef, to be served in boxed luncheons at the Women's Pavilion.
500

What year were the White Sox founded?

The White Sox were one of the American League's eight charter franchises in 1901.

500

What Chicago building is regarded as the world's first skyscraper? 

The Home Insurance Building, completed in 1885.
The first multi-story building to have an iron frame. It was demolished in 1931.

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