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100

Name a current Cubs player

Who is Matthew Boyd, Ben Brown, Porter Hodge, Shota Imanaga, Brad Keller, Julian Merryweather, Daniel Palencia, Ryan Pressly, Colin Rea, Ethan Roberts, Jameson Taillon, Caleb Thielbar, Jordan Wicks, Miguel Amaya, Carson Kelly, Jon Berti, Vidal Bruján, Michael Busch, Nico Hoerner, Matt Shaw, Dansby Swanson, Justin Turner, Gage Workman, Pete Crow-Armstrong, Ian Happ, Seiya Suzuki, Kyle Tucker?

100

This elevated train system, whose nickname is a single letter, loops through downtown "Chicago" 

What is the "L"? 

100

This is Adam Sandler's favorite sport

What is basketball? 

100

This braided egg bread is traditionally eaten on Shabbat and Jewish holidays

What is challah? 

100

This former First Lady and best-selling author was born and raised on Chicago’s South Side and graduated from Princeton and Harvard Law

Who is Michelle Obama? 

200

The Cubs ended their long championship drought by winning the World Series in this year

What is 2016? 

200

Unlike New York-style pizza, Chicago’s signature deep-dish version is traditionally baked in this kind of pan

What is a cast iron (or round) pan? 

200

This Jewish baseball pitcher famously refused to pitch on Yom Kippur and is now a Hall of Famer

Who is Sandy Koufax?

200

These crispy potato pancakes are often served with applesauce or sour cream during Hanukkah

What are latkes?

200

Known for her groundbreaking talk show that aired for 25 years in Chicago, this media mogul also founded her own television network

Who is Oprah Winfrey? 

300

This Hall of Fame second baseman, known for his incredible .358 career batting average, won seven National League batting titles and played for the Chicago Cubs during the 1920s

Who is Rogers Hornsby?

300

The Willis Tower, formerly known by this name, was once the tallest building in the world.

What is the Sears tower? 

300

He was the first Israeli basketball player ever drafted into the NBA

Who is Omri Casspi?

300

Popular at Passover, this dense, fruit-filled dessert is made from a mix of dried fruits and nuts and has a name that means "mixture" in Hebrew

What is charoset? 

300

This visionary Chicago architect coined the phrase “form follows function” and is remembered for his ornate facades and influence on modern skyscrapers

Who is Louis Sullivan? 

400

The Cubs’ iconic ballpark is known for this colorful feature that runs along the outfield walls

What is the ivy?

400

This Chicago neighborhood is home to the famous "Cloud Gate" sculpture, also nicknames "The Bean" 

What is Millennium Park? 

400

This Jewish-American tennis legend won 18 Grand Slam singles titles and helped advance women’s sports

Who is Billie Jean King?

400

A common Ashkenazi appetizer, this dish features chopped hard-boiled eggs mixed with onions and rendered chicken fat

What is chopped liver?

400

This Chicago-born poet and author of “We Real Cool” became the first Black woman to win the Pulitzer Prize for Poetry

Who is Gwendolyn Books? 

500

This Cubs pitcher threw a no-hitter in 2021, helping lead the team’s pitching staff

Who is Zach Davies?

500

This 1893 event marked Chicago’s emergence as a world-class city and introduced innovations like the Ferris Wheel

What is the World's Columbian Exposition? 

500

At the 1952 Helsinki Olympics, this Jewish gymnast won six medals, including four golds

Who is Ágnes Keleti?

500

Traditionally served with horseradish, this jellied fish dish is made from ground freshwater fish like carp or whitefish

What is gefilte fish?

500

This controversial Chicago-based artist and activist is known for her large-scale public installations like “The Dinner Party” and for pioneering feminist art in the 1970s

Who is Judy Chicago?