Chicago Trivia

50+ Best Chicago Trivia Questions & Answers

Mike Oberman

Updated: August 17th, 2023

Get ready to test your Chicago trivia knowledge with this collection of trivia questions! See how much you know about the city's its iconic architecture to its rich history. These questions will take you on a tour of the Windy City.

Chicago Known for Trivia

Question: What famous food is Chicago known for?

Answer: Deep dish pizza

Question: What famous Chicago street is known for its shopping and dining?

Answer: The Magnificent Mile

Question: What famous Chicago street is known for its music clubs and live entertainment?

Answer: Rush Street

Question: What famous Chicago street is known for its art galleries and studios?

Answer: Oak Street

Question: What famous Chicago street is known for its historical architecture and cultural landmarks?

Answer: Michigan Avenue

Question: What famous Chicago street is known for its trendy bars and nightlife?

Answer: Wicker Park

Question: What famous Chicago street is known for its outdoor markets and street festivals?

Answer: Randolph Street

Question: What famous Chicago street is known for its upscale restaurants and boutiques?

Answer: Armitage Avenue

Question: What famous Chicago street is known for its eclectic shops and independent businesses?

Answer: Division Street

Question: What famous Chicago street is known for its trendy coffee shops and independent bookstores?

Answer: Lincoln Avenue

Question: What famous Chicago street is known for its trendy clubs and live music venues?

Answer: Clark Street

Question: What famous Chicago street is known for its historical landmarks and cultural attractions?

Answer: State Street

Question: What famous Chicago street is known for its famous theaters and performing arts venues?

Answer: Broadway

Question: What famous Chicago street is known for its famous music festivals and outdoor concerts?

Answer: Grant Park

Question: What famous Chicago street is known for its famous art fairs and cultural events?

Answer: Old Town

Question: What famous Chicago street is known for its famous farmers markets and outdoor events?

Answer: Daley Plaza

Question: What famous Chicago street is known for its famous food festivals and culinary events?

Answer: Navy Pier

Question: What famous Chicago street is known for its famous cultural festivals and parades?

Answer: Western Avenue

Question: What famous Chicago street is known for its famous sports events and facilities?

Answer: Soldier Field

Question: What famous Chicago street is known for its famous recreational facilities and parks?

Answer: Lincoln Park

Question: What famous Chicago street is known for its famous entertainment venues and movie theaters?

Answer: State Street

Question: What famous Chicago street is known for its famous tourist attractions and landmarks?

Answer: The Loop

Question: What famous Chicago street is known for its famous music clubs and live entertainment?

Answer: West Loop

Question: What famous Chicago street is known for its famous art galleries and studios?

Answer: River North

Question: What famous Chicago street is known for its famous shopping and dining destinations?

Answer: The Magnificent Mile

Question: What famous Chicago street is known for its famous cultural attractions and landmarks?

Answer: Lakefront Trail

Chicago Facts and Sports Trivia

Question: What is the name of Chicago's professional baseball team?

Answer: Chicago Cubs

Question: What is the name of Chicago's professional football team?

Answer: Chicago Bears

Question: What is the name of Chicago's professional basketball team?

Answer: Chicago Bulls

Question: What is the name of Chicago's professional hockey team?

Answer: Chicago Blackhawks

Question: What is the largest city in the state of Illinois?

Answer: Chicago

Question: What is the nickname of Chicago?

Answer: The Windy City

Chicago Landmarks Trivia

Question: What body of water is Chicago located on?

Answer: Lake Michigan

Question: What is the highest building in Chicago?

Answer: Willis Tower

Question: What famous public park is located in Chicago?

Answer: Grant Park

Question: What famous art museum is located in Chicago?

Answer: The Art Institute of Chicago

Question: What famous science and technology museum is located in Chicago?

Answer: The Museum of Science and Industry

Question: What famous aquarium is located in Chicago?

Answer: Shedd Aquarium

Question: What famous zoo is located in Chicago?

Answer: Lincoln Park Zoo

Question: What is the name of the famous Chicago theater district?

Answer: The Loop

Question: What famous university is located in Chicago?

Answer: The University of Chicago

Question: What famous observatory is located in Chicago?

Answer: The Adler Planetarium

Question: What famous Chicago street is known for its famous recreational facilities and parks?

Answer: Jackson Park

Question: What famous Chicago street is known for its famous entertainment venues and movie theaters?

Answer: Lincoln Square

Question: What famous Chicago street is known for its famous tourist attractions and landmarks?

Answer: Navy Pier

Question: What famous Chicago street is known for its famous music clubs and live entertainment?

Answer: Wrigleyville