CollegeVine College Essay Team September 1, 2025 21 Essay Guides 2025-26,University of Chicago

How to Write the University of Chicago Essays 2025-2026

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 seven incredibly outside-the-box prompts (with the seventh 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 the one applying for admission. 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 This School?” essay. Here’s what we recommend in order to set yourself apart:

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 a student wanted to write about the Creative Writing internship, they should explicitly state how it draws them 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 → Your 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.

As with all UChicago prompts, this is a creative essay that asks you to think imaginatively, show your personality, and connect curiosity with intellectual depth. You have up to two full pages to do this, and should make the most of this space by writing an essay that is original, authentic, and engaging. So, what’s the best way to do this?

First, consider how each part of the prompt works together to build to a particular purpose. Let’s say you want to learn about communication. Choosing to interview a whale could shed light on how contact can happen across vast distances. Bees would instruct you on novel forms of expression, from the scents that float off flowers to the way that the right series of dance steps can lead the way to a new patch of clover. Wolves coordinate across pack members on the best way to bring down a flagging elk. Don’t just consider communication—think about which animal gives you the best angle to your particular question. 

That’s the next part of the prompt to think carefully about; you want a specific angle on a subject, not a general lecture. The more specific and sophisticated your question, the more you demonstrate your capacity to think deeply, as well as potentially showing off the depth of your understanding about a species’ unique attributes. Whatever you choose, make sure to connect your interest to a human challenge, or a passion or interest of yours. As cool as animals themselves are, they aren’t the focus of this prompt.

Your choice of species and question should make it clear why this conversation matters, but it also doesn’t hurt to state that explicitly. Broader insight into the world, deep awareness of personal values, and connections to your own goals, interests, and future will make this essay personal and make it stand out. 

This is a lot to balance, so let’s take a look at some hypothetical examples of students who do a good job incorporating every element of a successful answer.

• A Budding Psychologist: Chats with crows about memory, tool use, and problem-solving, reflecting on what it means to be human and how animals and humans can and do work together.
  

• An Environmentalist: Communicates with whales about ocean health and the underwater experiences humans can’t access, from infrasonic sound to sights we’ll never see. 

• A Philosopher: Asks jellyfish, immortal creatures without brains, how they “experience” existence, reflecting on consciousness and what it means to be alive.

Each of these students chooses a unique animal that has a fresh, unexpected angle on a passion or even a future career of theirs. We see new ways of looking at old problems, an appreciation for an animal’s unique qualities, and catch a glimpse of what’s most important to these students and what their best qualities are. 

Another playful creative prompt from UChicago, this one targets your ability to explore cause-and-effect in a nuanced way, blending analysis with imagination while once again showing what you value and are curious about without telling it directly. 

Maybe you have a thousand ideas for un-invention or maybe you’re still thinking, but either way, let’s start strategizing. What does a good answer look like? 

First, while creativity is encouraged here, you don’t want to be silly with your answer. For example, saying you would un-invent alarm clocks so no one would have to wake up earlier than they’d like doesn’t reveal much of anything about you because it’s a surface-level reasoning for a fairly common invention. However, if you focused on the snooze button specifically, and justified it by exploring the implications on procrastination, personal responsibility, and productivity, that would make a much stronger essay.

It’s also crucial that as you explore the ripple effects, you don’t get lost in the analysis. Remember, this is still a college essay so you need to connect the effects of this un-invention to you and your interests, rather than going down a rabbit hole of explaining the granular impacts. For example, if you chose to un-invent the “like” button on social media, don’t focus your discussion on what that would mean for big tech companies and the advertising industry.

Instead, a more powerful essay would be one that provides a personal connection. Perhaps you talk about how disingenuous it feels when you hang out with your friends because you are always thinking about getting the perfect photo for Instagram so you can get likes. Uninventing this feature would allow your generation to be more present and less focused on artificial gratification which could lead to increased mental health, more creativity, etc. 

Notice how you can still explore the ripple effects while keeping it centered around your experiences as well? This is what you should strive for.

Also, remember that UChicago wants to see your capacity for nuance. Un-inventing anything would be quite complex, so show that you have thought through the positives and negatives of your idea. Take the example of un-inventing plastic. If you solely discussed the positive environment benefits, it might seem like you are approaching the topic through rose-colored glasses. In contrast, if you discuss the financial challenges of switching to biodegradable materials and the burden it could place on developing nations, it shows your appreciation for deeper thinking.

All UChicago essays call for creativity combined with intellectual rigor, so what sets this prompt apart is the ripple analysis—what’s unraveling, and why it matters. This is your essay, so make sure you’re writing about something that matters to you. 

Out of a set of prompts that ask for creativity and deep engagement, the qualities that set this one apart are its appreciation for tension and paradox. This is a good pick if you’re a very self-aware person who believes in nuance and gray areas, and are ready to explore your own life in a complex and layered way. This prompt has more of a focus on you than some of the others, so you’ll want to put a lot of yourself into it. Let’s talk about how to do that. 

First, let’s brainstorm some contronyms.

• Have you ever had to serve two very different roles, or been in two positions that asked very different things of you?
• Think of a time when your values were tested. Do you have any deeply held values or beliefs that at times contradict each other?
• Has your way of viewing a situation or the world ever stood in opposition to the way most others saw it? Maybe a mechanic is traditionally seen as a builder, but your time fixing cars taught you it’s more about breaking problems down into pieces. 
• Perhaps different people see very different sides of you. Have others ever described you in contradictory ways? Have you ever described yourself in contradictory ways?

When you’ve chosen a contradiction in yourself to write about, brainstorm different stories or situations that best illustrate that duality. Often, it’s a good idea to rely on showing without telling the admissions committee what you mean, as examples and anecdotes are both memorable and specific. You want to tell the admissions committee more about you in a unique way, so focus on stories that are vivid, personal, and have some depth to them. 

It’s important to note that you aren’t required to pick a specific word to base your essay off of like the prompt does. You can easily write an engaging essay about something in your life that has two sides to it without boiling it down to a single word with a dual meaning. However, some students might find it helpful to use a singular word as a jumping off point to guide their essay, and in that case, go for it!

Let’s look at a sample of what a strong response could look like. 

The student chooses a word that allows for rich reflection, a vivid metaphor, and an essay that can move in many different directions. Expanding this excerpt to a full two pages will mean adding in anecdotes and deepening the reflection, but hopefully this gives you an idea of how you can explore a contronym.

What sets this prompt apart from UChicago’s other prompts is its focus on change and the meaning you can assign objects otherwise seen as superfluous. This is another introspective prompt, where the significance you assign is far more important than a traditional cost/benefit analysis. In that spirit, let’s brainstorm some questions about what at-risk item might be worth arguing for. 

• What’s sentimental to you? Do you have mementos or keepsakes like Polaroids or cassette tapes that are little used now but hold special significance?
• Are there any older technologies you still use or appreciate, like a typewriter, fountain pen, or even a sundial?
• Are there small objects that connect you to a hobby or passion? Common examples might be postage stamps for an avid letter writer or heritage seeds for a gardener. 
• Is there anything that has familial significance to you? Like your grandpa’s pocket watch he always wore or your mom’s rollerblades from the 80s.

When selecting a topic, consider the deeper significance of the item to you, specifically Perhaps it triggers nostalgia, or continued use speaks to sustainability. Maybe this connects you to the past, or to others around the globe. Whatever it is, try to choose something that goes beyond mere sentiment and holds deeper significance. Remember, this essay will be two pages long, so you’ll have plenty of time to dig deeply into how this object speaks to you.

A good response will choose an object with personal resonance—don’t choose landline phones because you like the retro look, choose them because they were a key part of your weekly calls to your grandparents growing up and they speak to a broader topic of intergenerational communication that you feel is lacking. The latter makes for a far more compelling essay.

You’ll also want to weave in the broader cultural or symbolic meaning your object (or the removal of it) holds. For example, maybe you choose paper checks as the focus of your essay. The broader significance of writing a paper check meant that people were forced to slow down and consider their purchases more intentionally, promoting better financial habits and less rampant consumption.

Balancing your personal connection and the larger significance is key for this essay to demonstrate your appreciation for the topic. It reveals personal information about yourself and your past, while also showing how you think about and approach the world.

Finally, try your best to avoid cliché items. Things like physical photographs or handwritten letters are fairly commonplace items that will pop into most people’s heads upon reading this prompt. While you can still choose to write about these items—you will need to have a truly unique angle to stand out if you go down this road—we recommend brainstorming for a few days to develop an essay that is uniquely you. Be observant and introspective as you go about your day, and hopefully you will come up with small items that you treasure.

This prompt is a little less personal than some of the others, giving you more of an opportunity to flex your research and analytical skills. Here, the name of the game is connections, as UChicago wants to see you draw links between seemingly unrelated products. Your imagination and ability to innovate will be on display, so make sure you’re choosing a brand and brand extension that builds on it. 

The brand you choose can help demonstrate your values and priorities, so consider carefully what you’re picking, whether it’s a cleaning products company or a gas station. Each company has a slightly different way of doing business, and the more specific you can be about why you’re choosing what you’re choosing, the better. This is also a great opportunity to show off your depth of knowledge for a particular industry or product!

After you’ve selected your brand, consider a real-world need that is in, or adjacent to, this brand’s sphere. You want to choose something that is surprising, but has an element of logic or “rightness” to it. Lastly, you want your chosen link to connect to your passions and your future at UChicago—after all, this essay is still about you, not a business pitch. 

All this might sound like a tall order, but hopefully the examples below will help show how it all can fit together into a cohesive essay.

• Camila, aspiring neuroscientist: Camila has always been fascinated by how music affects the brain. She could propose that Spotify launch a neuroscience-informed “Focus Mode,” curated by scientists, that uses tempo, rhythm, and binaural beats to optimize memory and concentration. This bridges her interest in brain science and her daily habit of studying with lo-fi playlists.
  

• Jonah, sustainability advocate: Jonah’s family runs a small farm, and he’s deeply invested in reducing food waste. He could suggest that Tupperware launch a biodegradable container line that doubles as seed starters once it’s done storing leftovers—an idea that merges his agricultural roots with his environmental goals.
  

• Anika, future anthropologist: Anika grew up listening to her grandmother’s stories about growing up in Kerala. She might propose that Duolingo launch an oral-history platform where users not only learn a language but also record elders’ stories in that tongue—preserving both culture and memory.

Each example connects a well-known brand to a potential new market, a connection that not only solves a problem in the world, but also speaks to the student’s interests, values, and way of seeing solutions. 

Even in a list of unusual UChicago prompts, this one stands out as perhaps the most unusual. Here, you’re asked to argue that correlation implies causation, intentionally choosing two trends that almost certainly do not reflect an underlying association. This is a test of your imaginative playfulness, your argumentation abilities, and your appreciation for connections where there may be more than meets the eye. Let’s dive in. 

Here are some angles to consider as you develop your essay.

• What weird or funny spurious correlations fascinate me?
• How could I argue that there’s actually a “causative truth” behind the nonsense?
• Can I tie this argument back to a personal value, hobby, or worldview? (e.g. if you love cooking, margarine and divorce might become a metaphor for family dinners).
• Do I want my essay to lean silly, satirical, or surprisingly serious?

A strong essay will not only pick an unexpected correlation and make a strong case for their connection, but it will all connect back to the student. At the end of the day, while this is a lighthearted prompt, deeper significance is what will make it, and you, memorable to the admissions committee. Make sure to balance your humor with real substance. 

It’s also worth noting that some spurious correlations are best left alone. While you might be able to spin a strong argument for the connection between Nicholas Cage movies and deaths by drowning, making light of the latter can leave a bad taste in admissions’ officers’ mouths. When there is a serious side to the statistics you’re using, make sure to treat the subject with the respect it’s due. 

Let’s take a look at a brief excerpt that skillfully incorporates all of these elements. 

Although this essay has a playful tone, it also discusses a serious topic that the student is passionate about. The level of detail incorporated throughout this short excerpt shows the reader that this student is knowledgeable about both pirates and contributing factors to global warming. Additionally, the essay is argued in a convincing and clear-to-follow structure.

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 that they expect a disciplined, thorough, and rigorous essay. Don’t let your sense of fun 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. 

As with all the other prompt options, you still need to show your personal connection to your topic in this essay. 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 that is totally unique to you. 

If you’re 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 it does serve as the hook of your essay—is not where its substance lies. 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 expanded upon 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.

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