Monsters of the Midway
(Chicago Bears + Football World)
Dynasty on the Hardwood (Chicago Bulls + Global Football)
North Side & South Side (Cubs, Sox & Cricket)
On Ice and In the Confines (Blackhawks, Wrigley & World Soccer)
Windy City Grab Bag (Mixed Chicago + Cricket/Soccer)
100

Which Chicago Bears running back was nicknamed “Sweetness”?

Walter Payton
100

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

Six 

(1991, 1992, 1993, 1996, 1997, 1998)

100

 In what year did the Chicago Cubs break their World Series championship drought in the 21st century?

2016

100

How many Stanley Cups did the Blackhawks win between 2010 and 2015?

Three (2010, 2013, 2015)

100

Which Chicago stadium is located on the shore of Lake Michigan and is known for its colonnades?

Soldier Field

200

Who was the head coach when the Bears won Super Bowl XX?

Mike Ditka

200

Who was the head coach during all six of the Bulls’ championship seasons?

Phil Jackson

200

In what year did the White Sox last win the World Series?

2005

200

In which arena do the Chicago Blackhawks play their home games?

The United Center

200

What does ICC stand for in cricket’s governing body?

International Cricket Council

300

What famous defensive scheme used by the ’85 Bears is known by a number?

"46 Defense"

300

Which player hit “The Shot” over Craig Ehlo in the 1989 playoffs against the Cavaliers?

Michael Jordan

300

How many players are on the field for one cricket team?

11

300

Which country won third place at the 2022 FIFA World Cup?

Croatia

300

Which Chicago team had a famous mascot named “Da Bull,” playing on the city’s accent?

The Chicago Bulls

400

How often is the men’s FIFA World Cup held?

Every 4 years

400

Which three countries are hosting the 2026 FIFA World Cup?

United States, Canada, and Mexico

400

Which MLB crosstown rivalry series is played between the Cubs and White Sox?

The Crosstown Classic (also called the Windy City Classic/Series)


400

What is the name of the song traditionally played after Blackhawks goals at home?

“Chelsea Dagger” by The Fratellis

400

Where is FIFA, world soccer’s governing body, headquartered? 

Zurich, Switzerland

500

Who was the Bears’ starting quarterback in the 1963 NFL Championship Game victory over the New York Giants?

Bill Wade

500

efore Phil Jackson took over as head coach, who was the Bulls’ head coach immediately prior to him?

Doug Collins

500

The 1919 White Sox scandal involving players fixing the World Series is commonly known by what name?

The Black Sox Scandal

500

Which Chicago team’s fans traditionally sing “Take Me Out to the Ball Game” with a celebrity guest during the 7th inning stretch?

The Chicago Cubs

500

Which national team is considered the most successful in Cricket World Cup history?

Australia