How to Write the University of Chicago Essays 2020-2021: The Scholar’s Guide

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The University of Chicago has an acceptance rate of 8.4%, and its application process can be daunting for even the most stellar applicants.

The school is well known for its rigorous academics, heavy emphasis on scholarship, and beautiful campus. Prominent alumni include over 50 Rhodes Scholars, NBA commissioner Adam Silver, Microsoft CEO Satya Nadella, and astronomer Carl Sagan.

If you want to attend the University of Chicago, you need to be serious about and dedicated to your chosen academic field.

The school prioritizes writing across the disciplines, so you want to make sure your supplemental essays are tidy, insightful, and maybe even a little offbeat.

This guide will help you write the best essays for this top school:

What are the University of Chicago Supplemental Essay Requirements?

You’ll need to write two essays when applying to the University of Chicago.

The first – “Why The University of Chicago?” – doesn’t change. It’s the well-known “Why This College” essay  that has the ability to show the admissions committee that you’re made for the University of Chicago as much as it can turn the committee toward keeping you away.

The second, the extended essay, is a choice from a series of quirky and provocative questions inspired by current students and alumni. These prompts change every year. Luckily, there are seven prompts available and you only need to choose one, so you can easily pick the one that shows off the best pieces of yourself.

The “Why Chicago” Supplemental Essay:

“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.”

This essay is a prologue to your masterwork, the extended essay. Like all good prologues, this is the “hook” which will spark the interest of the admissions officer and keep their attention. Ask yourself, “What will pique his or her interest?”

There is a pretty clear clue in the words “particular” and “specificity.” UChicago makes it very explicit: They want students who own and love their unique subculture and singular curiosities and know how they will thrive at their university. Here are some examples of how “particular” and “specificity” can be portrayed in this essay.

  • It’s good to write “I love literature written by marginalized groups,” but it’s better to say something like “I have a penchant for Spanish-language literature published in urban centers in the United States.”
  • Rather than write “I really enjoy rock music,” you can express that “Although I enjoy the majority of rock music, my tastes tend toward 1980s Hair Metal and Glam Rock, which I’m constantly explaining the difference to my friends.”
  • Instead of “I’m fascinated by the study of genetics,” write about how you “love reading research related to twin theories because I have had some experiences with my twin that are difficult to explain scientifically.”

The first example also shows the admissions office that their commitment to the South Side of Chicago will align with your commitment to urban literature. The last one could be relevant in the research around quantitative biology and human behavior at UChicago.

Ties like this are both important and impressive, if you can naturally fit them into your piece.

The prompt also wants you to focus on your “learning,” “community”, and “future.” While you don’t necessarily want three equal paragraphs that focus on each one, you want to be sure to cover each of the bases throughout, so you should brainstorm each before you begin.

The following thought processes will work well for UChicago, as well as most “Why This College” essays you write.

When considering your learning:

  1. Ask yourself “What are my values?” Check out a core value chart, choose two or three that stand out right now, and write them down.
  2. The academic questions that inspire your curiosity are likely connected to these values.
  3. If you value “balance,” for example, you might be interested in questions pertaining to health, fitness, mental wellness, and the human body.

In order to identify your studies:

  1. Ask yourself “What sorts of questions drive my studies?”
  2. So, you’re good at physics? This is fine, but it’s not enough. What is it about physics that motivates you?
  3. Tell them how you get lost in thoughts about gravitational time dilation while getting a haircut, or how your interest in aerodynamics was inspired by an inquiry about the dimples on golf balls.

When considering your community:

  1. Ask yourself “What type of people do I spend my time with? What are their dreams, what makes them sad, and what makes them laugh?”
  2. Take a look at the University’s student organizations page and see if any of the 400 groups appeal to you. “How would I thrive at the University of Chicago?” If you’re a West Coast surfer, maybe you’ll aspire to start a Great Lakes Surf Club. If you like hiking or trail running, maybe you’ll organize weekend groups to trek the Indiana Dunes.
  3. Think about how you will balance your academics and the rest of your life.

When considering your future:

  1. Ask yourself “What sort of mark would I like to make in the world?” Think beyond, “I want to make the world a better place.”
  2. Maybe you want to make the workplace more equitable or help change the values of the pharmaceutical industry.
  3. You don’t have to be definitive about your career, or even your major, but you do want to have some kind of vision that aligns with your values. How will the resources of UChicago support this vision?

You will want to look up specific programs and classes. For example, if you’re interested in international business, describe how you plan to double major in Chinese and Economics and then spend a semester in Beijing.

  • Discuss what you hope to accomplish during your time there and what type of internship or experience will help you reach that achievement.

You’ll probably also want to take a campus tour. If you’re not able to visit the campus in person, take a virtual tour, meet with representatives at a college fair, and look at their brochures. Do your homework so you can speak with sincerity about the resources of UChicago, and how you can see yourself flourishing there.

  • While the essay has no instructions regarding word count or structure, the admissions office advises to stay between 250-500 words.

Remember to keep your essay specific, and avoid generalities like “I will excel given the school’s rigorous academics.”

Tell them which academics, and how you will excel. Remember to cover everything – learning, community, and future – while artfully balancing both your aptitudes with an awareness of UChicago’s strengths and resources.

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The University of Chicago Extended Supplemental Essay

The University of Chicago’s selectivity makes their quirky extended essay prompts all the more intimidating. Maybe this is another example of the school’s offbeat sense of fun.

In past years they’ve asked questions about odd numbers, vestigial structures, and mantis shrimps. There are some brief yet totally compelling prompts like, “Find x.”

  • All of their questions evoke a sense of play, and should demonstrate the applicant’s capacity for creative, incisive thought.

As the admissions office puts it, “We think of [the extended essay] as an opportunity for students to tell us about themselves, their tastes, and their ambitions. They can be approached with utter seriousness, complete fancy, or something in between.”

UChicago doesn’t give you a strict limit, but advises you to keep it under 650 words.

The following are a list of the 2020-2021 prompts, with tips and examples to help you as you brainstorm:

University of Chicago Supplemental Essay Option 1

“Who does Sally sell her seashells to? How much wood can a woodchuck really chuck if a woodchuck could chuck wood? Pick a favorite tongue twister (either originally in English or translated from another language) and consider a resolution to its conundrum using the method of your choice. Math, philosophy, linguistics… it’s all up to you (or your woodchuck).”

—Inspired by Blessing Nnate, Class of 2024

This is an intriguing prompt because when you first read through it, it sounds completely whimsy. Then you get a little further and realize it’s giving you a one-of-a-kind chance to show off your knowledge and/or innovation within your chosen major (or another academic field).

Let’s break this prompt into two pieces.

First, they’re looking for something unique and even a little bit silly. They want to see that you are creative, and that you’re able to think outside of the box.

Start by brainstorming through the tongue twisters you grew up memorizing. If no brilliant ideas pop up after a few minutes, search the internet for a few tongue twisters you may have forgotten about.

Keep in mind that tongue twisters can be translated from another language, opening up your options significantly. This is a wonderful option if you grew up in another country or if you speak more than one language, as it gives you the opportunity to show the admissions team even more about what makes you you.

When you look into a tongue twister, try to answer the following questions:

  • What is the protagonist’s conflict?
  • Could its solution fall within your desired major or another academic field?
  • Is the potential solution unique and intriguing?

Once you’ve got your riddle, you’ll need to relate it to that academic field. If you’ve got an excellent idea from another subject, it’s definitely okay to go that route. However, we recommend relating the tongue twister to your own major. This will show the admissions team at the University of Chicago that your knowledge and out-of-the-box thinking are needed within your future major’s department.

Some other tips for writing this essay include:

  • Make the majority of your word count about the solution. That unique way of thinking is what UChicago really wants to see here.
  • Showcase a bit of who you are, whether that’s through a tongue twister from another culture or just from choosing a solution within your chosen major
  • Be unique! Even if your answer seems a bit crazy, that ingenuity is sure to help you stand out from the thousands of other applications being submitted this year.

University of Chicago Supplemental Essay Option 2

“What can actually be divided by zero?”

—Inspired by Mai Vu, Class of 2024

When you first read through this question, it might not even make sense. Of course, nothing in math can be divided by zero. So how do you answer this question? You relate it to real life.

Once again, if a creative thought pops into your head right when you read through the prompt, run with it. Those “light bulb” ideas are often the best ones.

If you don’t have an idea right away, don’t disregard this prompt just yet.

Read it ten, twenty, even thirty times. Read it in your mind and then read it outloud. Call a friend and ask them the question (without taking their answer, of course, just to find the necessary motivation).

  • Is there anything around you that exists but should go to no one?
  • Is there a theoretical item that no one should have or no one deserves?
  • What about something that is nothing already, so it can be divided by zero without really changing at all?

Remember, this is not a math question, even if it is talking about numbers and division (unless you’re a future math major with a genius idea on how this could actually work in the numerical world; then, go for it).

Most answers to this prompt, however, are going to be theoretical.

Use this platform to share about an issue you care about or one of your deepest passions (when applicable).

It’s a tricky question, but don’t limit your creativity. Come up with an answer no other applicant will submit. What could make your application stand out more than an essay that is 100% unique in every possible way?

Make the admissions team think in a way they never have before. What could impress them more than that?

University of Chicago Supplemental Essay Option 3

The seven liberal arts in antiquity consisted of the Quadrivium — astronomy, mathematics, geometry, and music — and the Trivium — rhetoric, grammar, and logic. Describe your own take on the Quadrivium or the Trivium. What do you think is essential for everyone to know?

—Inspired by Peter Wang, Class of 2022

This essay prompt is partially great for history majors, and partially great for creative storytellers.

Have you studied up on what Quadrivium and Trivium were in ancient times?

Are you passionate about all things Medieval?Then this prompt may be perfect for you.

Even if the Medieval times aren’t really your thing, you can get pretty creative with bringing these terms to our current times.

Start by researching the ins and outs of Quadrivium and Trivium.

  • If these were the only two majors today, which would you choose and why?
  • What type of careers would come from Quadrivium majors? And Trivium majors?
  • Does everyone need to choose one major, or will each student need to study both?

Once you describe how these two fields of study could exist in our world, describe why every person would need to know both.

Include the details of Quadrivium and Trivium in Medieval times, as well as the specifics of how they’d look today.

Remember to be creative. Show off your storytelling skills, and don’t forget to include a few details that help the admissions team get to know you.

Maybe you’re a college student getting ready to study the two fields? WHat do you hope to learn and why?

Have fun with this topic; If one thing’s for sure, we know it’s not meant to be boring!

University of Chicago Supplemental Essay Option 4

Subway maps, evolutionary trees, Lewis diagrams. Each of these schematics tells the relationships and stories of their component parts. Reimagine a map, diagram, or chart. If your work is largely or exclusively visual, please include a cartographer’s key of at least 300 words to help us best understand your creation.

—Inspired by Maximilian Site, Class of 2020

This is another prompt that is really meant to get your creative juices flowing. Pick a map, diagram, or chart and get to work.

How will you choose which schematic to redesign?

Consider choosing something that is related to the place you grew up, giving you yet another chance to allow the admissions team to get to know you.

  • Do you live in the heart of New York City? Consider going with the Subway maps.
  • Are you a future medical student? Mix up the estimated growth charts that pediatricians use.
  • Do you love history? Maybe even scramble up the order of the years that have gone by.

Once you’ve chosen your map, diagram, or chart, it’s time to get creative.

What crazy thing would happen if what you’ve chosen was all mixed up?

  • Do homosapiens evolve backward, bringing us closer and closer to our days as apes?
  • Do the subway tunnels and tracks involve some crazy twists and turns, allowing them to spell out an ever-important word or phrase?

Whatever you think up, fill your essay with detail and bring it to life. Take the admissions team into your mind, showing them a small piece of who you are along with a large chunk of your incredible, unprecedented imagination.

University of Chicago Supplemental Essay Option 5

“Do you feel lucky? Well, do ya, punk?” – Eleanor Roosevelt. Misattribute a famous quote and explore the implications of doing so.

—Inspired by Chris Davey, AB’13

This essay is almost too easy to believe in our current society where misinformation is constantly being spread on the internet.

It’s the perfect prompt for a journalism or English major, as you can demonstrate the power of words along with your ability to use them in an outstanding fashion.

First, pick a historical figure (or even a well-known person who is still alive today).

Look into who they are and what they are known for.

Then, find or create a quote of your own that they would never say in a million years.

It could be against their beliefs, It could be outside of their personality. It could be completely strange and random. The limits here are endless.

You can make the admissions team laugh, make them think, or show them something you’re passionate about.

  • Maybe a two-party politician comes up with a real plan for peace that involves both sides coming together.
  • A historical figure could prophesy about the danger of a future filled with electronics.

No matter what you choose, make sure it’s obvious that the person would have never said it. Make the admissions team stop and think, “What did I just read?”

At the same time, though, make sure you’re writing for a purpose. Show a piece of who you are or what you’re capable of. It is a college application you’re writing for, after all.

University of Chicago Supplemental Essay Option 6

Engineer George de Mestral got frustrated with burrs stuck to his dog’s fur and applied the same mechanic to create Velcro. Scientist Percy Lebaron Spencer found a melted chocolate bar in his magnetron lab and discovered microwave cooking. Dye-works owner Jean Baptiste Jolly found his tablecloth clean after a kerosene lamp was knocked over on it, consequently shaping the future of dry cleaning. Describe a creative or interesting solution, and then find the problem that it solves.

—Inspired by Steve Berkowitz, AB’19, and Neeharika Venuturupalli, Class of 2024

This prompt is for all of you entrepreneurs and future inventors out there. It is often said that inventing and business-founding is a passion, it’s not something that just happens. It’s the way you are and the way your brain works. You want to do something new, solve a problem, etc.

If this sounds like you, get ready to allow all of those inventive juices to flow right out onto the page.

The admissions team wants you to use this prompt to show them your ingenuity and what you’re capable of creating from the power of your own brain.

Start by thinking back to a problem you’ve experienced in life. It could have been yesterday, last year, or even when you were a child.

Now, find a solution. This solution could be real, it could be a hypothesis, or it could be completely made up. The prompt never says it has to actually work. It just has to show your potential for future innovation.


  • Be creative
  • Show the admissions team who you are and what you’re capable of
  • Give your essay a fun flare

No matter what your invention is, if you’ve got that entrepreneurial passion, your essay is sure to be a hit with UChicago.

University of Chicago Supplemental Essay Option 7

In the spirit of adventurous inquiry (and with the encouragement of one of our current students!) 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!

The University of Chicago prides itself in its unique prompts written by current and former students. They change every year, but that doesn’t mean you can’t take advantage of a prompt you fell in love with last year while applying right now.

This question allows you to take any questions that have been offered as part of the UChicago application in the past and use them for the current year.

You can find a long list of old prompts here, but we’ll list some below to give you a little inspiration as well:

  • Due to a series of clerical errors, there is exactly one typo (an extra letter, a removed letter, or an altered letter) in the name of every department at the University of Chicago. Oops! Describe your new intended major. Why are you interested in it and what courses or areas of focus within it might you want to explore? Potential options include Commuter Science, Bromance Languages and Literatures, Pundamentals: Issues and Texts, Ant History… a full list of unmodified majors ready for your editor’s eye is available here.

—Inspired by Josh Kaufman, AB’18

  • Alice falls down the rabbit hole. Milo drives through the tollbooth. Dorothy is swept up in the tornado. Neo takes the red pill. Don’t tell us about another world you’ve imagined, heard about, or created. Rather, tell us about its portal. Sure, some people think of the University of Chicago as a portal to their future, but please choose another portal to write about.

—Inspired by Raphael Hallerman, Class of 2020

  • The mantis shrimp can perceive both polarized light and multispectral images; they have the most complex eyes in the animal kingdom. Human eyes have color receptors for three colors (red, green, and blue); the mantis shrimp has receptors for sixteen types of color, enabling them to see a spectrum far beyond the capacity of the human brain. Seriously, how cool is the mantis shrimp: What might they be able to see that we cannot? What are we missing?

—Inspired by Tess Moran, AB’16

Again, this prompt is really something you can turn into anything.

If none of the six essays from this year’s application inspire you, use this as an opportunity to find the perfect fit that really shows off who you are and what you’re capable of.

When you choose the right essay, your unique attributes will shine through and the University of Chicago will likely take note.

Conclusion: Writing the University of Chicago Supplemental Essays

The University of Chicago is a school that prides itself on academic, quirks, and offbeat traits. When writing your essays, don’t be afraid to demonstrate your uniqueness and vulnerability.

If you have special interests or perspectives that weren’t mentioned in your other supplemental essays, the University of Chicago essay is a great place to input those quirks.

The admissions site says these essays “can be approached with utter seriousness, complete fancy, or something in between,” so really let your real personality shine.

Always check your work, revise with precision, and strive to craft a narrative.

Compelling and unique essays are key when it comes to earning yourself a ticket for admission to UChicago.

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