Landmarks & Architecture
Chicago History
Sports
Neiborhoods & Districts
Food and Drinks
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100

This iconic landmark is known for its unique "bean" shape and reflective surface.

Cloud Gate 

100

In 1871, this devastating fire destroyed much of Chicago and led to a major rebuilding. 

The Great Chicago Fire

100

This Chicago stadium was home to both the Cubs and White Sox, at different times, before it was demolished in 2021

Comiskey Park 

100

This vibrant downtown neiborhood is known for its skyscrapers, proximity to Grant Park, it lies just south of the downtown commercial district. 

South Loop 

100

A "Chicago Handshake" is traditionally composed of these two components 

Old Style, and a shot of Malort 

100

Fill in the blank " United Auto Insurance _________, we got you covered, Chicago."

773-202-5000

200

This historic theater opened in 1921, is famous for showcasing vaudeville and live performances, is located in downtown Chicago. 

Chicago Theater 

200

On February 14th, 1929, seven members and associates of George "Bugs" Moran's Northside Gang were gunned down in a Chicago warehouse by four men posing as police officers.

Saint Valentines Day Massacre 

200

Daily Double

write down your wager now.


















After winning the World Series in back-to-back years 1907 and 1908, the Chicago Cubs would go in to hold the longest droughts not winning the World Series until this year.

2016

200

This historic neiborhood was a major center for jazz music during the 20th century

Bronzeville

200

The original deep-dish pizza was created at what Chicago restaurant in 1943?

Pizzeria UNO 

200

Whether you remember that uncomfortably blank stare or the sheer monotony of his voice, this attorney is a household name for his trademark Chicago commercial. And not to mention, his unbelievably cringe-worthy Chicago accent.

Peter Francis Geraci 

300

Designed by Fredrick Law Olmsted and Calvert Vaux, this massive park is home to the Buckingham fountain and Millenium park.

Grant Park 

300

In 1968, a major riot broke out in Chicago during this political convention 

Democratic National Convention 

300

In Superbowl XX (1986) the Chicago Bears would defeat this team 46-10

The New England Patriots 

300

This neighborhood in the West Loop is famous for its trendy restaurants, art galleries, and annual food festival. 

Fulton Market 

300

What tavern is famous for both its "cheezborgers" and for its curse on the Chicago Cubs?

Billy Goat Tavern 

300

Who does this phone number belong to?

588-2300

Empire Carpets

400

This Gothic revival skyscraper, completed in 1889, is one of Chicago's oldest and most architecturally significant buildings, serving as the tallest building in the world for a brief period. 

Tribune Tower 

400

This act of organized crime during Prohibition in the 1920's saw infamous Gangsters like Al Capone rise to power on Chicago in commonly called

Bootlegging Era/ Gangster Era 

400

In what year would the Chicago Fire leave their 14-year home in Toyota Park, for the historic Soldier Field

2020

400

This neighborhood is home to the Museum of Science and Industry 

Hyde Park 

400

What fast-food giant has their corporate headquarters in the Chicago suburb of Des Plaines

McDonalds 

400

A ’90s Chicago classic with unforgettable hair and a creepy talking eagle.

Eagleman (Eagleman Insurance) 

500

Designed by Frank Lloyd Wright, this library building is renowned for its modern design and innovative use of space. 

Robie House 

500

In 1919, Chicago was the site of a bombing at a labor rally, which became a pivotal event in the U.S. labor and political history 

Haymarket Bombing/ Haymarket Riots 

500

This iconinc Chicago Blackhawks goaltender is known for his "Save of The Century" in the 2010 Stanley Cup Playoffs

Corey Crawford 

500

This neighborhood, once site of the famous meatpacking industry and its associated stockyards, played a significant role in Chicago's industrial history  

Back Of The Yards 

500

What are the 6 toppings of a Chicago Style Hotdog (not including poppy seed bun, and celery salt) 

Yellow Mustard

Relish 

Chopped white onion 

Sliced Tomatoes 

Pickles (pickle spears)

Sport peppers 


500

From hot links and baby spareribs to chitlins, catfish and chicken wings, this Chicago staple was the place to get the freshest cuts of meat and fish.

Moo and Oink