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.

Ah, the good ol’ ‘why this school?’ prompt! It might feel like you can rinse and repeat this essay for different schools, but we’d strongly caution against that! While, sure, some pieces might be consistent for you across schools—say, the major you plan to apply to and how you want to translate that into a career—UChicago wants you to articulate not only what you will study at Chicago and where you’ll go after, but how the University of Chicago and you together would have magical synergies that attending another school wouldn’t provide in the same way.

Yes, the U of C is an elite and prestigious school, but it’s not for everybody. The question is not just ‘are you smart enough?’ but ‘are you nerdy enough?’ Do you spend time after your BC calc or Medieval History course geeking out on the topic with that friend that totally gets you? (Maybe that friend is your teacher??) If so, read on! If your idea of the ultimate collegiate experience involves big football games that the whole school attends in school colors and facepaint… you may wish to look elsewhere. The academic rigor of the University of Chicago has earned it the moniker ‘the place where fun goes to die’ among students. While students might spend more time in the library at U of C than at peer institutions, this is likely less about UChicago having more coursework than those other institutions, than it is about UChicago being home to the highest per capita rate of students who consider discussing Foucault on a Friday night ‘fun’. (Facts!)

To be clear, the people who pick UChicago LOVE UChicago. They’re finally in a place with peers who can match their geek freak. Something about that notion, that folks who end up there are the U of C type, is core to the school’s identity. So, when you’re identifying aspects of the University of Chicago that attract you, there are two ways to go about it:

1. Identify things about the ‘learning’ and ‘community’ at UChicago that other candidates might rather AVOID (aspects of the school that might cause these other candidates to prefer a different elite university). Then explain why you’re actually THRILLED about these things, and how they align with your future goals.
2. Find things that only exist at U of C and nowhere else—or things whose UChicago version is somehow unique—and as such, align better with your desires for your ‘learning, community and future’ than other schools’ versions. Again, there may be an element here of ‘others might want to avoid these quirks, but they’re what make me WANT to go to the University of Chicago’.

Again, pay attention to their language in the prompt: ‘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.’

Let’s break this down. They say, ‘learning, community and future’; they’re looking for a through-line from your ideal college experience to your ideal post-college life. This through-line can center your intended major -> career trajectory, but it doesn’t have to. Maybe you really want to study public policy in the best public policy department, and UChicago Harris has XYZ features that align perfectly with the change you want to be in the world. But the through-line could also be… U of C Professor Martha Nussbaum’s takedown of Judith Butler totally opened your eyes to the ‘hip defeatism’ at your school, and you realized you needed to reframe your entire approach to activism going forward in your life, and want to be in an intellectual environment that feels more ideologically diverse to you than all those lefty left schools out there. 

Make sure your answer wouldn’t be equally true of any peer institution OR any student with equivalent ‘stats’, quantitatively. The question is ‘Why UChicago?’ and not ‘Why elite institutions?’ Otherwise, your unique fit for this school won’t be clear. 

While there’s no word limit, the UChicago Admissions FAQ page suggests that 300-600 words is a good ballpark. Wherever your word count nets out, make sure you’re still editing these essays as rigorously as ones that do cap the word count. 

Question 2: Extended Essay (Required; Choose one)

The Extended Essay—formerly called ‘The Uncommon Essay’, back when the UChicago application was ‘The Uncommon Application’—is another example of UChicago being idiosyncratic. It’s an invitation for you to showcase your creativity, your own idiosyncrasies, and your unique voice. Again no word limit, but the U of C FAQ page says that 500-700 is a good benchmark.

While you want to think and write a bit outside the box for this one, you still should connect the essay back to your experience, interests, etc. It’s an opportunity to showcase your creative writing, yes, but we generally advise you take any opportunity to tell a school more about the amazing things you’ve done, experienced and are. In this case, the lens of this essay may be a bit unconventional, but it should still reflect you.

There’s no right way to approach these. Our recommendation is that you do a bit of brainstorming on each of the prescribed essay options (1-5). Then go back and see which option(s) most tickles you creatively AND most clearly connects to your experiences, plans and/or values. Draft that essay with the prompt’s exact language in mind, but if the content ‘wants’ to take you in a different direction, you can leverage Option 6 (choose your own adventure / topic of your choice). 

We’ll share our thoughts below each option, but keep in mind that these are NOT hard-and-fast rules. If your coolest essay flies in the face of our general guidelines, you do you, friend!—that’s the point of this essay, after all. Our one full-throated piece of advice is, don’t let the unconventional prompts fool you into thinking that structureless and untethered musings cut the mustard. The structure doesn’t need to look like a classic 5-paragraph essay you’d write for school, but the essay needs to be considered, crafted and edited. 

Essay Option 1

We’re all familiar with green-eyed envy or feeling blue, but what about being “caught purple-handed”? Or “tickled orange”? Give an old color-infused expression a new hue and tell us what it represents.

– Inspired by Ramsey Bottorff, Class of 2026

Synaesthetes to the front! (Seriously, though, if this is you, go to town!)

Write a list of idioms that include color, then next to each, free-associate about any other colors that would give a particular meaning to the phrase. Have fun with the exercise. Once you’ve done some free-writing for each option, come back and see how these (could) connect back to you, compared to the other essay options. 

Essay Option 2

"Ah, but I was so much older then / I'm younger than that now” – Bob Dylan. In what ways do we become younger as we get older?

– Inspired by Joshua Harris, Class of 2016

OK, so, a word of caution here—while we don’t doubt that your experience on this earth to date has been complex, layered and ever-evolving, keep in mind that the average age of adcom officers is likely 20 years north of your age. If you write the essay from your own perspective as a teen but unironically affect the gravitas of an octogenarian’s retrospection… it might sound a little presumptuous. Point is—as Cat Stevens said—‘you’re still young, that’s your fault, there’s so much you have to go through.’ (If you don’t know who Cat Stevens is, you’re just proving our point here.) You still have a lot of aging to do. To be fair, we acknowledge that some people go through experiences at a young age that make them grow up a lot faster than their peers. If this is your experience, that’s totally fair game. 

That said, the essay doesn’t ask about how YOU’VE gotten younger as you’ve aged. You can reflect on aging you’ve observed around you. 

Looking back on your life, what can you honestly say has changed as you’ve aged? What has changed as those around you have aged? Make a list. See if any notable observations can be framed as a sort of getting younger. Free-write and see if there’s an interesting concept to unpack that’s personal to you in some way. 

Essay Option 3

Pluto, the demoted planet. Ophiuchus, the thirteenth Zodiac. Andy Murray, the fourth to tennis's Big Three. Every grouping has something that doesn’t quite fit in. Tell us about a group and its unofficial member, why (or why not) should it be excluded?

– Inspired by Veronica Chang, Class of 2022

For this one, make a list of ‘unofficial members’ and their associated groups that you have some feeling of connection to (emotionally, intellectually, practically, or otherwise). If you’ve got some very specific areas of interest and/or research, and a related answer pops to mind here, this may be an opportunity for you to geek out in a way that shows your genuine passion for learning. 

Remember, you need to make the case of WHY this excluded member should or shouldn’t be included… if you go this route, your POV shouldn’t just be the generally accepted rationale. Either ‘everyone things it shouldn’t be included but I think it SHOULD(!!) because XYZ’, OR ‘everything thinks it should be excluded because XYZ but REALLY it should be excluded because ABC!’ Don’t say something just to get a rise out of the audience… this one should be something you actually have a real opinion on.

Essay Option 4

"Daddy-o", "Far Out", "Gnarly": the list of slang terms goes on and on. Sadly, most of these aren’t so "fly" anymore – “as if!” Name an outdated slang from any decade or language that you'd bring back and explain why you totally “dig it.”

– Inspired by Napat Sakdibhornssup, Class of 2028

Those of us who were alive and watching MTV in the 90s feel personally attacked by this prompt’s implication that the slang of our youth is somehow outdated. (Or even the implication that we’re not ‘youths’ anymore—how dare! We’re pretty sure Y2K just happened a few months ago and Clueless was recently released.) BUT we can set this aside in the interest of helping you craft an awesome essay. 

Once again, start with a list. Whichever outdated slang words come to mind… maybe you have a personal association with them (e.g., your parent or other adult might have used it or talked about how it was used ‘back in the day’)... maybe not. Of those list items you like, jot down what they’d help you express if they were still in use, and why you’d bring them back. 

Remember, the prompt is about a word or phrase you LOVE and would bring back. It’s not an open referendum on old slang. A lot of old slang has not aged well, and plenty could be (and surely has been) written on why we’re better off without these words and phrases in common parlance today. While this may be an essay worth writing, it doesn’t answer this particular prompt. (Remember, you’ve always got Option 6 if any of prompts 1-5 lead you to an awesome topic that’s tangentially related.)

Essay Option 5

How many piano tuners are there in Chicago? What is the total length of chalk used by UChicago professors in a year? How many pages of books are in the Regenstein Library? These questions are among a class of estimation problems named after University of Chicago physicist Enrico Fermi. Create your own Fermi estimation problem, give it your best answer, and show us how you got there.

– Inspired by Malhar Manek, Class of 2028

Alright, for this last scripted prompt, jot down anything in your life or the world around you where the quantity just feels… beyond. Think about how you’d estimate it, the units you’d use, etc. The point is NOT to get the ‘correct’ answer, but rather to show how you think creatively about questions without a ‘correct’ or readily-accessible answer. It’s about how you quantify the seemingly unquantifiable.

The best essays will usually have some personal connection to your life… as there’s an opportunity to say something more about yourself while also walking the adcom through your creative thought experiment. But again, maybe it just reflects on you insofar as it lets your geek flag fly and reveals a unique perspective on deep and specific interests. 

Essay Option 6

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!

Some Option 6 essays will stem from previous brainstorming that took a turn away from the prompt, some will not. If you’re in the former group, cool, keep going with your draft, edit well, and own it! 

If you’re in the latter group or you haven’t really connected with any of the above (admittedly oddball) prompts, consider this: As you look back over your entire UChicago application (including the Common App elements), which aspects of you—your engagements with the world, your inner life, your nerdy passions—have not gotten the airtime they really need? If the adcom ONLY had the rest of the application, what would they be missing from the full picture of you? Got a possible answer or two or three? Cool. 

Now, zoom out and imagine you’re writing an uncommon essay prompt. Get creative with your phrasing. To be clear, you don’t need to include a prompt that your essay responds to, but sometimes taking the perspective of ‘what questions could I be answering with this essay’ can help you ideate creative approaches that will allow you to cover topic X in an innovative way. Don’t force a weirdness—just allow your unique voice to come through. Edited, but not censored.