Travel Trivia: 20 CHALLENGING Questions About Chicago

Chicago is a premier US city that is popular with tourists from all over, itching to explore all the cool things to see and do. With Chicago being the birthplace of modern architecture, a special style of pizza, scientific and medical breakthroughs, and a gorgeous skyline, it truly is an incredible city. This is why we’ve made this trivia quiz about Chicago!

A cluster of skyscrapers along Lake Michigan at the beginning of sunset with just a strip of pink showing in the sky

And this isn’t just a regular quiz, there are some questions that may surprise you. And don’t expect this to be an easy one! So we kindly advise you to study up and read our Chicago facts post first, which will help IMMENSELY.

But if you’re up for the challenge, then carry on and take the quiz below. See if you have what it takes to answer 20 questions correctly about the Windy City. (And don’t forget to login below to claim your spot on our leaderboard).

Good Luck!

Travel Trivia: 20 Questions About Chicago

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Question 1 of 20

1. Question
What chocolaty sweet treat was invented in Chicago?
- Banana Split
- Sundae
- Brownie
- Black Forest Cake
Question 2 of 20

2. Question
Why is Chicago sometimes referred to as the ‘Second City’?
- Because it was the second city recognized in the United States
- Because it’s the second city in Illinois
- Because it was the second city to adopt two professional sports teams
- Because it was rebuilt after burning to the ground
Question 3 of 20

3. Question
The Bean is one of Chicago’s most recognizable landmarks. What is it’s real name?
- Coffee Stop
- Cloud Gate
- Giant Fortune
- Silver Cloud
Question 4 of 20

4. Question
Field Museum of Natural History – Chicago, Illinois

Chicago’s Field Museum of Natural History is home to SUE, one of the largest in the world of its kind on display. What is SUE?
- Robot
- Tyrannosaurus Rex
- Egyptian Mummy
- Kidney Bean
Question 5 of 20

5. Question
For largest population in the United States, where does Chicago rank?
- #1 – largest population in the USA
- Second largest
- Third largest
- Sixth largest
Question 6 of 20

6. Question
What type of pizza is Chicago famous for?
- Deep-dish pizza
- Thin-crust pizza
- Hawaiian pizza
- Stuffed-crust pizza
Question 7 of 20

7. Question
What serious discussion was broadcasted on television for the very first time in America by Chicago’s CBS channel in 1960?
- The Ed Sullivan Show
- The Presidential debate
- Julia Child's cooking show, The French Chef
- Gilligan’s Island
Question 8 of 20

8. Question
For what reason does the Chicago River get dyed green every year?
- For St. Patrick’s Day
- To kill harmful bacteria
- So it looks pretty (otherwise it would be brown)
- For Christmas Day
Question 9 of 20

9. Question
What life-saving endeavor first got its start in Chicago in 1937?
- Blood bank
- Fire Department
- FBI
- Search and Rescue
Question 10 of 20

10. Question
What high-rising invention was unveiled at the Chicago World’s Fair in 1893? Hint: Some of the biggest ones in the world reside in Dubai, London, and Las Vegas.
- Skyscraper
- Roller coaster
- Ferris Wheel
- Drop tower
Question 11 of 20

11. Question
To get to the heart of the matter, what medical operation was successfully performed for the first time in Chicago at Provident Hospital, the city’s first non-segregated hospital in 1891?
- Liver transplant
- Appendectomy
- Cataract surgery
- Open-heart surgery
Question 12 of 20

12. Question
The Chicago Theatre on State Street

What defining period of time began in Chicago?
- Atomic Age
- Bronze Age
- Mesozoic Era
- Cold War Era
Question 13 of 20

13. Question
The Chicago Times-Herald race was America’s first-ever automobile race and took place in November 1895. The track ran from downtown Chicago to Evanston and back again; participants built their own ‘road carriages,’ as the term ‘automobile’ had yet to be coined. What day did it take place?
- Memorial Day
- Veterans Day
- Thanksgiving Day
- Valentine’s Day
Question 14 of 20

14. Question
True or False? The historic Route 66 begins in Chicago.
- True
- False
Question 15 of 20

15. Question
True or False? The world’s first skyscraper was built in Chicago in 1885.
- True
- False
Question 16 of 20

16. Question
True or False? Chicago has its own version of Central Park, called Millennium Park.
- True
- False
Question 17 of 20

17. Question
True or False? Chicago’s O’Hare International Airport is currently the busiest airport in the world.
- True
- False
Question 18 of 20

18. Question
The name ‘Chicago’ comes from the Algonquin word, shikaakwa, which means ‘wild onion’ or ‘wild garlic’.
- True
- False
Question 19 of 20

19. Question
True or False? Michael Jackson is one of the many famous artists that have called Chicago home.
- True
- False
Question 20 of 20

20. Question
True or False? The Chicago River flows backward.
- True
- False