CollegeVine College Essay Team October 23, 2024 26 Essay Guides 2024-25,University of Chicago

How to Write the University of Chicago Essays 2024-2025

The University of Chicago is famous for its unconventional supplemental essay prompts, and this year is no exception. While there is one traditional prompt that asks you to write about your interest in UChicago, the star of your essay package will be your response to one of six incredibly outside-the-box prompts (with the sixth being a choose your own adventure).

Because the brainstorming you’ve done for all your other college essays is unlikely to help much here, you want to make sure you leave yourself extra time to really give these prompts the attention they require. One thing you’ll quickly realize is there’s no way to “brute force” your answer—you just need to be patient and let your ideas develop.

In this post, we’ll break down each prompt for you, so that, while you’ll still have to harness your own creativity, you can be confident in your overall approach.

Read these UChicago essay examples written by real students to inspire your own writing!

Before You Begin Writing 

The University of Chicago’s prompts are famous (infamous? both?) for being different, quirky, and sometimes downright weird. Have you ever seen the word cheese or pie in a college essay prompt before? I’m guessing not. But don’t get discouraged or overwhelmed—the weirdness of the UChicago prompts makes them ripe with opportunity to explore your passions, interests, and personal oddities. 

You know that subject you avoid in casual conversation, because it turns you into a gushing ball of enthusiasm that could talk for hours? UChicago wants to hear about it. Whether it’s feminist literature of Southeast Asia, modern perception of African art, or your job at Colonial Williamsburg, UChicago has happily passed you the mic. 

While your creative opportunity has few bounds, there are some key strategies to conquering the UChicago essays. Keep this checklist of things in mind as you write: 

Unconventional topics often require unconventional styles. 

UChicago essays should definitely be viewed as a piece of creative writing, rather than a dry analysis. When you are in college, you will be asked to write thesis-driven essays, but that’s not what the UChicago essays are asking for. You need to have a clear focus, but you should be comfortable disrupting the familiar rhythms of essay prose.

Strategies can include vivid (and we mean vivid) imagery, addressing the reader directly, sentence fragments, CAPS, lists, and anything else! Toss in some wild jargon from your field, phrases from another language, anything you’ve got—as long as you explain them. You should try to be imaginative, engaging, and colorful while maintaining an authentic voice and staying focused with your subject matter.

Communicate who you are as an academic.

The point of your essay is still to tell admissions officers about yourself. Give them an image of how you will perform in and contribute to an academic environment. You can’t just gush about your topic—you have to prove that you can engage with it at a highly intellectual level. Explain research protocol, cite specific books you’ve read, mention your AP and IB classes, or give examples of how you’ve collaborated with others to produce results. 

UChicago admissions don’t want a student who says “I love physics”; they want a student who says “I love physics so much that I stayed up until 4 am reading Cosmos by Carl Sagan, and I use meatballs to diagram the moons of Jupiter to my friends, and I took Calc III because I plan on studying mechanical engineering with a focus on aerospace materials.” Be detailed about your studies; be explicit in your interests. 

Marry yourself to your topic.

Be sure to include the first person; you are the main character here, not whatever subject you’re writing about. The subject is an avenue to tell admissions officers about you. You aren’t trying to get your latest film, your famous lasagna, or your community service project into the university—you are trying to get in. Don’t be afraid to center yourself. How do these objects from your past illuminate facets of your personality? What do your interests say about you?

And, as always, answer the prompt!

Print out the prompt, circle key words, hang it on your mirror. Read it, then read it again, and again. Sit with the prompt, get some (probably crazy!) ideas, then repeat the process! Many UChicago prompts are dense in their weirdness. Some of them take time to even understand. Many prompts will reveal themselves to you in your everyday life (after you’ve read them over and over again). Some of them just take deep thought. The key is to keep thinking and focus on what the prompt is asking. You’ve got this!

UChicago Supplemental Essay Prompts

The pressure’s on to be unique here, since EVERY SINGLE APPLICANT to UChicago will be answering this required “Why School?” question. Here’s what you need to do:

Provide a tangible connection to UChicago. 

This is composed of specific elements of the university that appeal to you, and UChicago’s website is a great place to delve into these. Be sure to be “particular,” as they stipulate, and give them the “specificity” they’re asking for. Examples include research opportunities at Argonne Labs, the marketing classes in the Business School, or an internship offered through the Creative Writing program. 

Don’t write about UChicago’s general attributes, like fame, prestige, or “intellectual rigor.” And please don’t try to be clever and refute the old canard that UChicago is the place “Where Fun Goes to Die.” Application readers have seen this hundreds, if not thousands of times. And besides, why talk about a tired UChicago stereotype when you can talk about something cool? 

Describe your intangible connection as well. 

How is UChicago a place that aligns with your values, dreams, and goals? How do you vibe with it? For example, if I wanted to write about the Creative Writing internship, I would state explicitly how it draws me in: 

Engage with faculty and students, if possible. 

This is a perfect place to talk about specific interactions, like sitting in on an inspiring seminar during a campus visit, hearing a professor speak, or seeing how UChicago has prepared a friend for his career. 

However, always be sure to tie these experiences into your own goals and interests! For example, don’t just name-drop a certain Professor Smith. Instead, take the opportunity to find a personal connection to Smith’s research and how great UChicago is for supporting people like her. Your format should be

        Program/Individual/Major – UChicago’s Values – My values

If you want to learn more about a specific professor or their subject, don’t be afraid to politely email them or contact their department. Many love to talk about their work and their interests, or would love to put you in touch with current students. This will better inform you about the school and give you a great edge for this prompt. And, more importantly, you’ll probably get great advice for your higher education journey. Note: the earlier you prepare for this, the better!

It’s worth noting that there is no recommended essay length, but sticking to around 500 words should do the trick. It’s long enough to share the reasons you’ll thrive at UChicago, but not too long that the admissions officers will start to get bored.

Brainstorming Your Topic

Like many of UChicago’s prompts, while the topic here is incredibly quirky, you actually do have a clear anchor for your brainstorming: expressions that include a color. To start your brainstorming, you’ll want to generate a list of such expressions, but to do so, we’d advise against just sitting there and wracking your brain.

Instead, you’ll likely find that trying to think of these expressions using context will be more productive. For example, think about whether there are any phrases you use often that could work. Maybe you’ve described yourself as a black sheep before, or when you talk about your best friend, you say they have a heart of gold.

Or, just glance around wherever you’re sitting, and see if anything inspires you. Maybe your mom’s Halloween decorations remind you of “white as a ghost.” Or the nice china that’s out for your dad’s birthday makes you think of being “born with a silver spoon in your mouth.”

The main thing is to just give yourself time, and jot down any potential options as they come to you. If you think of something during soccer practice, make a note to yourself on your phone during your next water break, and add it to your running list later. Don’t count on remembering something the next day–there’s no guarantee it’ll stick in your brain, no matter how brilliant it is!

Try to come up with 5-10 possibilities. You can have more if you want (although at a certain point continuing to brainstorm likely won’t be particularly productive), but you don’t want to have fewer. If you only have two to choose from, you might find that neither is strong enough to support a whole essay.

Once you have those possibilities, think about which ones speak to you the most, and then think of how you’d want to revise them, and which revised versions are most compelling. Which new color you choose, and why, is entirely up to you–maybe you just want to swap in your favorite color, or maybe you think first of what you want your new expression to mean, and work from there. 

Either way, remember that you shouldn’t be afraid to get creative! If you want to talk about being a periwinkle sheep, or having a heart of vermillion, you can do so. Just make sure you’ll be able to show that you have a reason for choosing such an unusual, specific color–you don’t want to seem like you just cracked open the thesaurus for fun.

Tips for Writing Your Essay

Once you’ve chosen your “new hue,” your focus should shift to the second half of the prompt: what it represents, as that’s what you’re going to spend your essay explaining. There are two main things you want to keep in mind as you write:

Creativity 

You’re probably already sick of hearing this tip, but UChicago wouldn’t ask such unusual questions if they wanted ordinary responses. So, don’t have your new hue represent the same thing but with a different color swapped in. For example, being a periwinkle sheep shouldn’t just mean you’re the most whimsical person in a group. 

Rather, try to show off your ability to put your own spin on something. Being a periwinkle sheep could instead mean that you have a lot of friends, but also a strong sense of your own identity–periwinkle is close enough to white that such a sheep could fit in, but also distinct enough that it will be noticeably different from the rest of the flock.

Your Own Personality

As unconventional as UChicago’s prompts are, ultimately your goal is the same as in any other college essay–you want to teach admissions officers about who you are, and why you’d be an asset to their campus community. So, your explanation of your new hue should connect to your own life, not just talk about the expression you’ve created in an academic sense.

For example, maybe you use the idea of a periwinkle sheep to explain how you’ve struggled to find your own identity in high school, and often latched on to different hobbies or friend groups, but since you discovered how much you love cooking, you feel much more grounded.

The connection doesn’t have to be this direct–you can still demonstrate who you are even if you wouldn’t use your new expression to describe yourself. As an alternative, you could draw a comparison between being a periwinkle sheep and doing puzzles, one of your favorite hobbies, by explaining how in a periwinkle sheep, like in a puzzle, you can simultaneously see all the different pieces of who they are and the full picture. You could then talk about some of your favorite puzzles over the years, and what you learned about yourself from assembling them.

However direct or indirect your approach is, make sure that you incorporate plenty of specific anecdotes and experiences from your own life. In other words, show, don’t tell. Just stating that you struggled to find your identity doesn’t teach admissions officers much, because that’s true of many people in high school. Instead, describe some of the specific things you latched onto while trying to find yourself, and reflect on how you felt about them at the time, whether positive or negative, and how you’ve grown since then.

Brainstorming Your Topic

This is the most open-ended of UChicago’s prompts this year, so if you’re a philosopher at heart, this could be the prompt for you! If, however, you want a little more structure to guide your thinking, you’ll likely want to choose one of the other options, which do more to provide you with a specific (if unconventional) topic.

If you do decide to tackle this one, you’ll want to start your brainstorming by asking yourself some broad questions, which will hopefully eventually lead you to a more focused idea that you can structure your essay around. For example:

• What do you associate with youth?
• What do you associate with growing older?
• Reflect on your own life: when you compare your childhood to today, how has the way you view the world changed or stayed the same?
• What are your goals for the future, and how do you see lessons from your past helping you achieve them?

Once you’re thinking generally about youth and aging, start trying to generate a list of memories or experiences you’ve had that reflect your thoughts about this topic. Grounding your ideas in specific examples will ensure that admissions officers can easily understand what you’re trying to say. 

Remember, they aren’t reading this essay by the fire at home–they’re reading dozens of essays a day. If there are any points they don’t immediately understand, they don’t have time to reflect on them, even if they’d like to, because they have so many applications to get through. So, clarity is absolutely essential.

For example, maybe you want to write about living in the moment. You might reflect on the happy summer afternoons you spent at your local playground as a kid, and how you could always find something to do. You could then think about how that connects to recent efforts you’ve made to spend less time on your phone, to encourage yourself to instead do things like play with your family dog, or help your parents with cooking dinner, that you won’t be able to do once you go to college.

Tips for Writing Your Essay

This is the kind of prompt where brainstorming is more than half the battle. Before you actually start writing, make sure you have a comprehensive outline that includes your overarching point, examples that illustrate that point, and the connections between these examples.

The connections in particular are key. Since the topic of this essay is so abstract, you want to make sure that you concretely connect each anecdote to the next. If you leave the connections up to your reader, they might not have time to make them on their own, and even if they do, there’s no guarantee they fit the different pieces together correctly.

Additionally, do keep in mind that this is still a college essay, which should demonstrate who you are, and in particular your readiness for this next step in your educational journey. Since this prompt is centered around your thoughts on quite a personal topic, making the connection between your ideas on that topic and your identity as a whole should be easier than with some of the other options. 

Still, you want to make sure that your readers–who, remember, are complete strangers with only a small amount of background context on you from your common app info session–will be able to identify key personality traits from your essay that will help distinguish you from other applicants. You don’t want to just seem reflective, as all applicants who respond to this prompt will likely come across as reflective.

Instead, think of more distinctive traits that you pride yourself on in general, like your sense of humor, your love of giving thoughtful gifts, or your passion for ancient history. Choose 2-4–you don’t want to go overboard, as then your essay will be difficult to follow–and think about how you can incorporate those details into your essay. 

You can do so in big ways, by choosing anecdotes that clearly illustrate them, or small ones, like a quick line comparing something in your life to the Egyptian Empire. The key is just that, after finishing your essay, UChicago admissions officers will understand what makes you, you, not just what you think about aging.

Mistakes to Avoid

Again, this is the most philosophical prompt, so you’ll want to take care that your essay doesn’t accidentally become too academic. Your goal isn’t to provide a template for how people should live their lives, but to explain how your thoughts on aging reflect your intellect, curiosity, and overall potential as a UChicago student. 

If you’re unsure whether your essay is striking the right tone, asking friends, teachers, or family members to take a look is a great idea. Someone who doesn’t already know what you’re trying to say can usually give you a more objective sense of whether what you’re trying to communicate about yourself is coming across clearly.

Brainstorming Your Topic

Like the first prompt, and unlike Option B, this option gives you narrow parameters for your brainstorming, which is both helpful, as you know what to focus on, and difficult, since those parameters are around a topic that you’ve likely never spent much time thinking about.

You’ll likely find that trying to think of unofficial members right off the bat will be challenging. Instead, start a step further back, with just groups. These could be sports teams, musical bands, groups of fictional characters, categories like the colors of the rainbow, or just about anything you can think of that refers to a well-defined set. 

Ideally, you’ll also have some personal interest in the groups you consider. If you think of the Rolling Stones because they’re your dad’s favorite band, but you don’t know anything about them, you’ll likely struggle to write an effective essay.

As you consider different groups, think about whether there’s an unofficial member. For a lot of groups, there might not be. But, as always with a UChicago essay, being creative is the whole point, so don’t discard any of your options without first thinking a little more deeply about them.

For example, maybe you’re thinking about ingredients, and your mind goes to s’mores. Even though most people probably wouldn’t think beyond the classic marshmallow, chocolate, and graham cracker, maybe your family has always included bananas, so that’s the “unofficial member” you want to write about. That totally works! If anything, other people not thinking of this idea is a positive–this is your essay, after all.

Your unofficial member can also be more obvious. Maybe you’re a huge Star Wars fan, and have always thought the main trio of Luke Skywalker, Han Solo, and Princess Leia should in fact be a main quartet, and include Chewbacca. This being a more widespread inclusion/exclusion debate shouldn’t scare you off. So long as you feel a genuine personal investment in Chewbacca’s inclusion in the group, you’ll be able to write an excellent essay on this topic.

One last thing to note is that the group, and unofficial member, you choose doesn’t have to be famous. UChicago says explicitly that they want you to tell them about the group, so it’s okay if they don’t have prior knowledge of it. You could even choose one from your personal life–for example, maybe one of your cats is a dog at heart, and always joins your two dogs on their romps in the backyard. 

While that kind of topic might seem mundane or silly, in reality extremely personal topics can often stand out the most, as there’s a much lower chance of anyone writing about something similar. Plus, the whole point of college essays is to give admissions officers a sense of who you are on a daily basis, beyond the numbers in your transcript and activities list, and an “ordinary” topic is often a natural way to provide that information.

Of course, there are countless ways to write a strong essay, so if you can’t think of a highly personal topic, don’t panic! Our point is just to not rule out such topics as you brainstorm, as they can often be highly effective.

Tips for Writing Your Essay

Like with many UChicago prompts, there are two prongs here: laying out an unusual topic for you, and then telling you what to do with that topic. Here, your task is to explain whether or not your unofficial member should be included, and why. Do remember, though, that your overarching goal is, as always, to use your justification to demonstrate something about who you are, and why you would be an asset to the UChicago community.

If, say, you’re using the s’mores example above, your argument for inclusion shouldn’t be based on the natural flavor of the banana balancing the other, processed ingredients. Instead, think about how your opinion connects to your values, or other key features of your identity.

For example, maybe you compare each ingredient to one of your core personality traits. The graham cracker could be your resilience, the chocolate your empathy, the marshmallow your love of daydreaming, and the banana your love of the outdoors. You could then justify your position by explaining how all four things are necessary to create a full picture of who you are.

Alternatively, for the Star Wars example, maybe you write about how, as a kid, you had a hard time making friends, and seeing a band of heroes which included a creature of another species was inspiring for you. You could talk about how Chewbacca gave you confidence that you could find belonging without changing who you are, and then describe how you carved out a key role for yourself on your high school volleyball team, despite not being tall.

If these justifications seem too personal, that’s actually a good sign! The point of this essay isn’t to convince the whole world to put bananas on their s’mores–the point is to convince UChicago admissions officers to accept you. So, the more personal, the better.

Along those same lines, you want to make sure to incorporate plenty of specific anecdotes. Don’t just say “I found belonging on my volleyball team.” Instead, describe how, at tryouts, you felt your familiar insecurity, until one of the coaches, who also wasn’t tall, took a personal interest in you and encouraged you to concentrate on your passing, with the goal of becoming a defensive specialist who wouldn’t need to play at the net.

The more you can let admissions officers live your experiences alongside you, and witness your thoughts and feelings firsthand, the more invested they will be in your candidacy.

Mistakes to Avoid

The biggest potential pitfall with this essay is choosing a group that isn’t clearly defined. Since your goal is to use your opinion on this matter to showcase who you are more generally, you don’t want to have to spend a whole bunch of space explaining what your group, and unofficial member, even is. Creativity is a plus, but shouldn’t come at the expense of being efficient with your words.

Brainstorming Your Topic

For the previous prompts, we’ve encouraged you to brainstorm your topic in an indirect way, because their focus is on such unusual things. For this prompt, however, just reflecting on your favorite slang expressions that have gone out of style will likely be effective, since slang by definition is something that you’re exposed to in everyday life.

You can also consider the following questions to further inspire you:

• Are there any books or movies from past generations that you enjoy? What kind of slang do they use?
• Are there any slang terms you’ve heard your parents, grandparents, aunts, uncles, etc. use that you enjoy?
• Have you ever watched or read an interview with a celebrity from the past and enjoyed a slang expression they used?

Note that, while the examples listed are mainly from the 60s-80s, UChicago is allowing you to cast a broad net, over slang expressions from “any decade or language.” So, if there’s a term you remember from your childhood, that’s fair game! You could even go further back, to terms you may have heard in movies from the 1900s, or even further back than that, to terms that you may have read in, say, Shakespeare.

If you know any other languages, you can also draw on them, but do remember that the term you choose still needs to be outdated. If you learned the non-English language in school, rather than natively, you might not know much about past slang, but resist the temptation to look up terms just to write a standout essay. You’ll need to justify your desire to bring back this term, after all, which will be difficult to do if you don’t actually know anything about it.

Tips for Writing Your Essay

Choosing a compelling slang term is key, but that’s just the first step to writing a strong essay. The bulk of your response will be dedicated to explaining “why you totally ‘dig it.’”

This explanation should go beyond just talking generally about liking the sound of the word, or feeling it picks out something distinctive that other words don’t quite capture. You can start there, but you should quickly get to making a connection between this word and your own personality. After all, the point of this essay isn’t to teach UChicago about a new piece of slang–it’s to teach them about you!

For example, say you choose the term “eighty-six,” which was used in the 1950s as a verb, which meant to throw someone out of a place. Maybe your elderly neighbor taught you this expression when you were helping him weed his garden as a kid, and you continued to weed together, “eighty-sixing” the invasive plants, all the way up until he passed away last year. You could talk about how he became a mentor for you during the time you spent with him in the garden, and 

The last thing you do want to make sure to do is actually answer the question, and explain why you want to bring this term back. Even if you tell a rich, captivating story, if you leave that element out, the essay will feel incomplete. You don’t have to spend a ton of space on it, but you do want to make sure your reasoning is connected to the story you’ve told. For the above example, a quick line in the conclusion would do the trick, along the lines of:

You don’t necessarily have to have a preexisting personal connection to the term you choose, although that will streamline your writing process. But if you’re thoughtful about meaningful experiences you’ve had that could have some relation to your term, you can definitely use the essay itself to make that link.

For example, say you instead had heard the term “eighty-six” in a movie, and had looked up the definition, but hadn’t thought much more about it, even though you thought it was a fun expression. 

In this essay, perhaps you reflect on how your affinity for the term shouldn’t be surprising, as many of your favorite activities involve eighty-sixing: as a diver, you’re always throwing yourself off the board; as an older brother, you love picking up your much younger siblings and throwing them onto the bed; and a lifelong dream of yours is to go skydiving, which you have been trying to convince your parents to let you do for your 18th birthday.

This essay might conclude with something like: “When I one day convince people to start saying eighty-six again, perhaps it will be with a new connotation: not just throwing someone out of something, but also into something new, and potentially wonderful.”

One last note: while the bulk of your essay should be explaining the significance of the term, you still do need to introduce it and provide a definition. There are a lot of different ways you can do this effectively, but one thing you definitely don’t want to do is just say “The slang term I would bring back is [x], which means [y].” Such a dry approach is unlikely to do anything to grab admissions officers’ attention.

Instead, describe the moment when you first heard this term, or an experience you’ve had that illustrates its meaning. This kind of “in medias res” (Latin for “in the middle of things”) strategy does much more to immediately get admissions officers personally invested in your story and curious about your personal perspective, compared to a literal definition that they could find in any old textbook.

Mistakes to Avoid

As always, creativity is of the essence. While the first terms that come to mind might be ones like “groovy” that are widely known as outdated, these likely won’t make as strong of an impression on admissions officers as ones that feel more distinct to you. As noted above, your ultimate goal is to use the term to illustrate something about yourself, and that will be easier if you choose a somewhat unique term.

Brainstorming Your Topic

Like Option D, as far as UChicago prompts go, this is one of the more straightforward ones to brainstorm for, as estimations are likely something you have occasionally wondered about in your regular life. Maybe you’ve often looked at your family’s pet parrot and wanted to know how many feathers she has, or you’re a soccer fan and you’d love to know how many miles Lionel Messi has run in games across his career.

One piece of advice that will help once you get to actually writing your essay is to brainstorm estimations that, like the examples above, have some connection to your personal life. As always, your goal is to use your quirky topic to shine light on some key aspects of your personality, and that will be much harder to do if your estimation doesn’t have anything to do with your interests or who you are. In other words, if you don’t like soccer, the Lionel Messi example probably won’t lead to a good essay.

One last thing to keep in mind: you can get creative with the actual thing you’re estimating. The examples given by the prompt include a “how long” question, not just “how many” ones. Some other things you could measure include:

• Weight: What is the total weight of all the kebab carts in New York City?
• Sound: How loud would every cat in the world purring simultaneously be?
• Speed: How fast would a cart being pulled by every horse in the world go?
• Price: How much would it cost to buy every item ever signed by Paul McCartney?

And don’t be afraid to even go beyond these suggestions!

Tips for Writing Your Essay

Once you’ve chosen a Fermi estimation problem, your task is twofold: answer it, and explain how you did so. But remember (especially if you’re a STEM person), this is a college essay, not a math problem. So, your goal actually isn’t to provide an accurate estimate, but to “solve” the problem in a way that shows UChicago how you think, and proves you have ability to get creative.

Your answer doesn’t even have to be an actual number. For example, you could “answer” the cats purring question poetically, by comparing the sound to other things–quieter than dogs barking, but louder than footsteps in fresh snow. You could also take a humorous approach, and say that Lionel Messi must have run at least 3 miles in his career.

Of course, you are also welcome to take an honest stab at the estimation. The specific approach you take is not what matters–what matters is that, in providing your answer, you teach admissions officers something about yourself. They aren’t reading this essay to actually learn how many feathers a parrot is, but to learn how well you would fit into the UChicago campus community, so that is the question that should be at the forefront of your mind as you write your essay–your answer should draw on your own experiences and background, not parrot feather density and your estimate for how many square inches of skin your bird has.

For example, maybe in justifying your earnest estimate of 2,318 feathers on your parrot, you talk about the summer you spent volunteering at a local owl rescue center, where you learned owls have around 10,000 feathers. You then talk about the yearly trips you have taken to visit your family in Puerto Rico, and how the drastic difference in climate between where you’re from and the tropics, your parrot’s native home, makes you think he would have about ¼ as many feathers as an owl.

Or, for one of the unconventional approaches, maybe in talking about all the world’s cats purring simultaneously, you contrast the comfort you got from your cat purring on your chest every morning with the motivation you got from your barking dog, which was abrasive enough to jolt you out of bed. You could then talk about losing your cat one snowy winter night, and how even though you were both soaked and freezing by the time you found her, and came down with pneumonia the day after, there was a peace in your reunion unlike anything you’ve ever experienced before.

Mistakes to Avoid

The main thing you want to avoid with this prompt is forgetting to respond to some piece of it. Remember, you’ve been given three tasks:

• Create your own Fermi estimation problem
• Give it your best answer
• Show us how you got there

The thing you’re most likely to accidentally gloss over is giving your best answer to the problem. While “showing your work,” aka explaining your personal connection to this estimation problem, should absolutely be the main focus of your essay, and, as noted above, your answer doesn’t even have to be direct, you do want to make sure you provide an answer of some sort. Given how much thought UChicago puts into choosing their essay prompts, you never want to leave any element unaddressed. 

Again, this prompt is, on the surface, granting you a lot of leeway. UChicago even ends it with an exclamation point! But you should always remember: they expect a disciplined, thorough, rigorous essay. Don’t let your sense of fun and frolic drown out your serious intellectual ideas.

Pick a prompt that inspires you to write, and connects with your academic interests. If a prompt jumps out at you, and you’re immediately filled with ideas, it’s probably a good fit. Just take it slowly, jot your thoughts down, and get to work. 

Involve your personal connection to that prompt. If you’re not answering any of the 6 prompts UChicago has issued this year, the onus is on you to prove that you and the archival prompt you’ve picked are a match made in heaven. This means having a lot of knowledge and personal investment in your subject matter, and an angle/perspective totally unique to you. 

If making your own question, remember this: YOUR QUESTION IS YOUR HOOK. So make sure it’s not a question that could be found on a standard-issue application, like “When did I overcome a challenge?” or “What’s a place that feels like home?” These prompts are everywhere. They won’t get the job done, and they won’t make an unforgettable first impression. But “Why did I lock myself in the basement and watch The Bee Movie for eighteen hours?” That’s a different story. 

If you look at past UChicago prompts, they tend to be fond of certain things: numbered lists, fairy tales, common phrases, and items of pop culture that can be re-contextualized. They also like hearing your answers to famous questions, and you might have a unique answer to “Et tu, Brute?” or “Do you like pina coladas and getting caught in the rain?” Just remember that the novelty of the question, while the hook of your essay, is not its substance. If your biography and scholarly interests don’t involve pina coladas, or rain, you might just have to pick a different question to answer – as wonderful as that eternal question is.

Final Tips

UChicago essays take a lot of time and thought—but don’t overthink it. The university wants to hear what you have to say, in its full form. That’s why they give you a page limit, and not a word limit—no last minute cutting! Fully develop your ideas in a way that feels natural. If a paragraph needs to be a little thicker, or if you need to include a longer quote from your favorite author, don’t worry about it. These essays can be fun to write and extremely effective.

You can look up lots of examples of essays online, but try not to get intimidated. It’s the nature of the UChicago essays to encourage everyone to showcase their expertise—which is exactly what you should try to do! You may read sample essays and think, “Wow. I’ve never spent a month in Arizona digging up fossils. How can I ever compete?” Try to reframe the essays as a Giant Celebration of everyone’s achievements and interests not a Competition.

If you’ve written your UChicago essay and are looking for feedback, you might want to check out our free peer essay review. Since the UChicago essay prompts are weird, it’s important to get an extra set of eyes on them to make sure they are clear and engaging! You can also improve your own writing skills by editing other students’ essays.

If you need feedback even faster, you can get a free, nearly-instantaneous essay review from Sage, our AI tutor and advisor. Sage will rate your essay, give you suggestions for improvement, and summarize what admissions officers would take away from your writing. Use these tools to improve your chances of acceptance to your dream school!