The University of Chicago supplemental essays are notorious for making students think outside of the box with unique questions crafted by current students and alums alike. Read below for advice on answering Chicago’s supplemental essays:

Question 1 (Required)

How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future? Please address with some specificity your own wishes and how they relate to UChicago.

In addition to the creative essay prompts below, UChicago also asks you to write a more traditional essay – essentially answering the question: Why the University of Chicago?

You’ll see this essay prompt from many universities’ applications, and it is a fantastic opportunity for you to expound upon why and how the college is a good fit for you. Is it the academics? Be specific. What about the campus, or size, or intellectual vitality? The college doesn’t need to hear about itself (U of C admissions officers work there, and some went there – they know what UChicago is!). Instead, talk about how you will fit in. Are there opportunities in Chicago that excite you, or professors with whom you would like to do research?

This question demonstrates the importance of visiting colleges. You cannot really learn that much from a website, though that is a great place to start. If you can meet with an admissions representative near you – either at a prospect program or at your high school or local college fair – that is a great start. But it’s even better if you can visit campus and take a student-led tour and listen to an admissions officer in an information session. On your visit, you’ll hopefully learn why UChicago is a great match for you.

Question 2: Extended Essay (Required; Choose one)

Essay Option 1

Exponents and square roots, pencils and erasers, beta decay and electron capture. Name two things that undo each other and explain why both are necessary.– Inspired by Emmett Cho, Class of 2027

There are so many routes to take with this. You can take the “academic” route, such as beta decay and electron capture, government and anarchy, multiplication and division. You can be straightforward, like pencils and erasers, sun and rain, clean and dirty. And you can have fun with it, like Batman and Superman, cats and dogs, BTS and One Direction. The sky’s the limit here; there is no “correct” response. Just be yourself and answer it the way that feels right for you. What you decide to write tells the admissions committee a lot about you!

Essay Option 2

“Where have all the flowers gone?” – Pete Seeger. Pick a question from a song title or lyric and give it your best answer.– Inspired by Ryan Murphy, AB’21

You can go with the well-known path here, like: 

“I said, hey, what’s going on?”

“Are you that somebody?”

“What’s my name again?

“Should I stay or should I go?”

Or any other famous ones you can find from Google (which you should also do if you don’t know any of the above examples).

But you can also choose a lesser known artist and song. Don’t force yourself into a song lyric; use any lyric that best fits you. (Maybe skip ones with profanity in them, but if you choose one with profanity, we recommend writing it like a comic strip: !$#%%#*.)

If you’re really into music, this could be the question for you! You have lots of other choices of essays, and the question you choose to answer says a lot about you. And, of course, your answer to the question in the song title should tell the admissions officers a bit more about who you are, how you think, what you like and what makes you unique. 

Essay Option 3

“Vlog,” “Labradoodle,” and “Fauxmage.” Language is filled with portmanteaus. Create a new portmanteau and explain why those two things are a “patch” (perfect match).– Inspired by Garrett Chalfin, Class of 2027

Everyday examples, inside jokes, nicknames… Use whatever comes to mind. Just make sure it isn’t mean-spirited, that the joke isn’t too inside, and you can write more than “it’s just a really fun word to say.” That last one – fun to say – can be one reason, just not the only reason.

Why did you choose the two words for your portmanteau? Why are they meaningful or significant to you? What does your new word mean (to you)? Are you interested in word origins and linguistics and etymology? Or are you a techie and that’s why “vlog” (or your version of vlog) appealed to you? The words that form your mash-up (portmanteau) should tell the admissions committee something more about you!

Essay Option 4

A jellyfish is not a fish. Cat burglars don’t burgle cats. Rhode Island is not an island. Write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept.– Inspired by Sonia Chang, Class of 2025, and Mirabella Blair, Class of 2027

Argue why an oxymoron isn’t actually an oxymoron. Explain why it’s actually okay to have two first names (think Michael Ryan). Defend your opinion despite it going against societal norms. Give scientific evidence. Give personal examples and experiences. 

The oxymoron you choose might not make sense to anyone else or change their mind, but make your argument compelling and it will at least be an engaging read. You want to give the admissions committee at the University of Chicago a glimpse into who you are and how you think and how you will contribute to the campus community.

Essay Option 5

Despite their origins in the Gupta Empire of India or Ancient Egypt, games like chess or bowling remain widely enjoyed today. What modern game do you believe will withstand the test of time, and why?– Inspired by Adam Heiba, Class of 2027

Backgammon is another great example of a game that has survived the test of time. You can pick a well-known game, like Connect 4 or Trouble. Or maybe it’s a game that has long-term potential to always be relevant, but will need continuous updating to fit into ever-changing societal norms (Monopoly comes to mind here). Or it can be a game that you’ve made up and that few people know about, but one that you believe will become more popular as time goes on. Finally, you can choose a game that you predict will make a comeback and be popular forever more. 

Be serious or have fun, just make sure you have a good argument. That is, be sure to explain why you chose your particular game. Was it meaningful to you when you were little (or now)? Did it bring you and your friends or family closer together? Perhaps you played this game with a grandparent, or maybe the game helped you learn a new skill (like math or a language). 

Beyond the game’s importance to you, be sure to answer the question asked. That is, why do you think your chosen game will withstand the test of time? What is so special about it? Why would every generation enjoy this game? Remember, the University of Chicago wants to learn about you, not about the game you’ve chosen to highlight.

Essay Option 6

There are unwritten rules that everyone follows or has heard at least once in their life. But of course, some rules should be broken or updated. What is an unwritten rule that you wish didn’t exist? (Our custom is to have five new prompts each year, but this year we decided to break with tradition. Enjoy!)– Inspired by Maryam Abdella, Class of 2026

This really covers everything. It can be societal, like: “Walk on the left and stand on the right in the US”. Or in baseball: “You hit one of our guys with a pitch, we’ll hit one of your guys.” Or in the Northeastern US: “Crosswalks and walk signals are just a suggestion and not a requirement.” Other ideas to consider include pet peeves and inconveniences – everything is on the table here. 

If you want to be especially bold, you can even praise the University of Chicago for breaking its own unwritten rule by expanding to six prompts rather than their traditional five!

As with the other essay prompts, the question you choose to answer should say something about you. What is your background? What is your story? Why, in this case, did you choose the unwritten rule that you wish didn’t exist? It’s not enough, of course, just to talk about the rule – you need to dig deeper and share more about you. Be vulnerable, be authentic, tell your story.

Essay Option 7

And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!

“Take a little risk, and have fun.” You’ve likely been writing several essays about an activity that you’ve taken part in, a specific program that you want to attend, or other topics that are more serious. Take this chance to think outside of the box and write something memorable and creative. Imagine a group of admissions officers sitting around a table reading hundreds of applications – what experience or aspect of your personality can you draw on to make the officer reading your essay look up and tell their colleagues about you? Don’t forget to write the question that you’re answering at the top of the essay.

About the author
Cecilia Yan

Cecilia earned a BA from University of Minnesota – Twin Cities and an MS from Boston University, where she focused her studies on public relations and marketing. Cecilia oversees graduate programs: business development, partnerships, marketing and counselors. She also works with China partnerships. Originally from China, Cecilia is a native Mandarin speaker.

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