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Turn your Chicago trivia notes into a pub quiz in minutes

Upload a PDF, slides, notes or a photo of a page and get multiple-choice, true/false or short-answer questions with explanations. No credit card needed to start.

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Drop files here or browsePDF, DOCX, PPTX, text or photos of your notes · several files with Plus

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Writing a round from your own trivia

Most Chicago bars that run trivia nights pull questions from local history, sports and city landmarks, and writing those rounds by hand eats up an afternoon. DeckOwl can do that drafting for you: upload your own notes and get a Chicago pub quiz set with answers and explanations ready to read.

Multiple-choice, true/false and short-answer questions from one upload
Explanations for each answer, so hosts can settle disputes quickly
Study in the browser on the free plan, with no credit card needed to start
Export to PDF or DOCX on Plus, and QTI or Moodle XML on Pro

Example Chicago general knowledge trivia questions

Which team ended a 108-year championship drought when it won the 2016 World Series?The Chicago Cubs, who beat the Cleveland Indians in seven games. The drought dated back to their 1908 title.

What is the official name of the stainless steel sculpture in Millennium Park known as The Bean?Cloud Gate, by Anish Kapoor. Its mirror-like surface reflects the skyline and visitors around it.

Which Chicago museum houses Georges Seurat's painting A Sunday on La Grande Jatte?The Art Institute of Chicago. The pointillist painting is one of its best-known works.

Why was the Chicago River reversed in 1900?To send wastewater away from Lake Michigan, which supplies the city's drinking water. The Sanitary and Ship Canal carried it toward the Illinois River instead.

What major event did Chicago host in 1893 to mark 400 years since Columbus reached the Americas?The World's Columbian Exposition. It drew large crowds and introduced many people to the city's growing architecture.

Generate the full set

Questions from your own material

Start from a city history handout, a sports almanac page or your own reading list. The generator writes questions from what you upload.

Explanations for every answer

Each question includes a short explanation, so the host can settle a disputed answer on the spot.

Export when you need it

Export to PDF or DOCX on Plus. Pro adds QTI 2.1 and Moodle XML for classroom quiz platforms.

How it works

Upload your notes

Add a PDF, DOCX, PPTX, plain text file or a photo of printed pages.

Choose the question types

Pick multiple-choice, true/false or short answer, or mix them across rounds.

Review and run the round

Check the answers and explanations, then read the questions aloud or export a printable copy.

If you were hoping to download ready-made Chicago quiz questions, this page is about writing your own. Use your reading list, a city history handout or a list of local sports facts, and the generator turns it into questions you can check against the source before the night.

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Frequently asked questions

How do I check trivia facts about Chicago before the quiz?

Compare each answer against a primary source such as the Chicago Public Library, the city's official website or the institution that owns the landmark. The explanation DeckOwl writes gives you a starting point to verify.

How many questions should a pub quiz round have?

Many hosts run rounds of about 8 to 10 questions so teams can finish a round in one sitting. Adjust the count to fit how long your night runs.

Can I export my pub quiz questions?

Yes, PDF and DOCX export are included in the Plus plan at $39/year or $7.99/month. QTI 2.1 and Moodle XML export are on the Pro plan at $14.99/month.

Is there a free plan?

Yes, the free plan includes 3 generations per month and lets you study in the browser, but it does not include exports.

Generate free quizzes

Keep exploring the topic

Review the main ideas visually or practice recalling them.