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Chicago Quiz: 12 Questions About the Windy City
Chicago rebuilt itself after a devastating fire and went on to invent the skyscraper. This Chicago quiz asks 12 questions on its landmarks, history and food.
Navy Pier, which stretches into Lake Michigan, was a recent Bing Homepage Quiz topic, so you will find it here too.
Play the Chicago Quiz
Pick A, B or C for each question. The right answer turns green and a short fact explains it.
Chicago Quiz Questions and Answers
Every question with its answer and explanation. Open “Show answer” after you guess.
1 Navy Pier extends into which lake?
- A Lake Michigan
- B Lake Superior
- C Lake Erie
Show answer
✓ Answer: A. Lake Michigan
Did you know? Chicago is the only major city on Lake Michigan's southwestern shore.
2 In which year did the Great Chicago Fire destroy much of the city?
- A 1906
- B 1871
- C 1929
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✓ Answer: B. 1871
Did you know? The fire burned for about two days in October 1871.
3 Who co-authored the 1909 Plan of Chicago with Daniel Burnham?
- A Frank Lloyd Wright
- B Louis Sullivan
- C Edward Bennett
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✓ Answer: C. Edward Bennett
Did you know? Burnham and Bennett's plan created much of the city's lakefront parkland.
4 What is the nickname of the Cloud Gate sculpture in Millennium Park?
- A The Bean
- B The Mirror
- C The Drop
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✓ Answer: A. The Bean
Did you know? Artist Anish Kapoor's sculpture is made of polished stainless-steel plates.
5 Which Chicago skyscraper was called the Sears Tower until 2009?
- A Willis Tower
- B Trump Tower
- C John Hancock Center
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✓ Answer: A. Willis Tower
Did you know? Completed in 1973, it was the world's tallest building for about 25 years.
6 Which building, completed in 1885, is often called the first skyscraper?
- A Home Insurance Building
- B Rookery Building
- C Flatiron Building
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✓ Answer: A. Home Insurance Building
Did you know? It used a steel and iron frame to carry its weight.
7 Which famous pizza style is associated with Chicago?
- A Thin-crust Neapolitan
- B Deep-dish
- C Detroit square
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✓ Answer: B. Deep-dish
Did you know? Deep-dish pizza has a high crust filled with cheese and topped with sauce.
8 What color is the Chicago River dyed for St. Patrick's Day?
- A Green
- B Blue
- C Gold
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✓ Answer: A. Green
Did you know? The tradition began in 1962 with a dye first used to find leaks.
9 Which attraction on Navy Pier gives views over the lake and skyline?
- A Space Needle
- B Gateway Arch
- C Centennial Wheel
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✓ Answer: C. Centennial Wheel
Did you know? The wheel opened in 2016 for the pier's 100th anniversary.
10 Which fair in Chicago introduced the first Ferris wheel in 1893?
- A Century of Progress
- B Pan-American Exposition
- C World's Columbian Exposition
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✓ Answer: C. World's Columbian Exposition
Did you know? George Ferris designed it to rival the Eiffel Tower of 1889.
11 Which Chicago baseball team won the World Series in 2016, ending a 108-year drought?
- A Chicago Bulls
- B Chicago Cubs
- C Chicago White Sox
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✓ Answer: B. Chicago Cubs
Did you know? The Cubs had last won in 1908.
12 Which famous U.S. highway began in Chicago?
- A Route 1
- B Route 66
- C Interstate 5
Show answer
✓ Answer: B. Route 66
Did you know? Route 66 ran from Chicago to Santa Monica, California.
About Chicago
Chicago is the largest city in Illinois and the third-largest in the United States. After the Great Chicago Fire of 1871 destroyed much of the center, the city rebuilt quickly and became a laboratory for new architecture, including the Home Insurance Building of 1885, often called the first skyscraper.
The 1909 Plan of Chicago by Daniel Burnham and Edward Bennett shaped its lakefront parks. Today Chicago is known for Millennium Park's Cloud Gate sculpture, the Willis Tower, the Chicago River, deep-dish pizza and its sports teams, from the Cubs to the Bulls.
Navy Pier
Navy Pier opened in 1916 as the Municipal Pier, extending more than half a mile into Lake Michigan. It was later renamed to honor Navy veterans of World War I and now holds shops, theaters and the Centennial Wheel. The July 16, 2026 Bing Homepage Quiz asked about the lake, the Plan of Chicago and the pier's attractions.
Chicago Quiz FAQ
Why is Chicago called the Windy City?
The name may refer to lake winds, but many historians link it to 19th-century boastful politicians and promoters, or 'windbags'.
Which lake is Chicago on?
Lake Michigan, one of the five Great Lakes.
What is the Bean in Chicago?
Cloud Gate, a reflective stainless-steel sculpture by Anish Kapoor in Millennium Park, nicknamed 'the Bean'.