Let's be real for a second. Most college applications are mind-numbingly boring. You spend months polishing a personal statement that basically says, "I am a hard worker who loves community service," and then you hit the University of Chicago. Suddenly, you aren't talking about your soccer captaincy anymore. You’re being asked about the history of the "middle" or what's actually under your bed. It’s weird. It’s meant to be weird. Honestly, the University of Chicago essay—specifically the "Uncommon Essay" prompts—is a gatekeeper. It’s the school’s way of checking if you’re actually one of them: a "nerd" in the most complimentary, intellectually obsessive sense of the word.
UChicago doesn't just want to see your GPA. They want to see how your brain functions when the lights are off and the guardrails are gone.
If you’ve looked at the prompts for the 2024-2025 cycle or even the legendary ones from the past (like "Where's Waldo, really?"), you know the vibe is different here. They don’t want a standard five-paragraph essay. They want a manifesto, a comedy routine, or a philosophical inquiry. Probably all three. It’s intimidating. But it’s also the only part of the application where you can truly have fun without worrying if you sound "professional" enough.
The Philosophy Behind the Madness
Why do they do this? Jim Nondorf, the Dean of Admissions at UChicago, has been pretty vocal about the fact that these prompts are actually written by current students. That explains a lot. It’s a peer-to-peer test. If you look at the prompt "What's so odd about odd numbers?" and your first instinct is to groan, UChicago might not be the place for you. But if you immediately start thinking about prime numbers, social outcasts, or the linguistic origins of the word "odd," you’re already halfway to an acceptance letter.
The admissions committee uses these essays to gauge "intellectual fit." They’ve already seen your SAT scores. They know you can do the work. What they don't know is if you’ll contribute to the late-night debates in the Harper Memorial Library. They are looking for "The Life of the Mind," which is basically the university’s unofficial motto.
It's about risk.
Most students are terrified of taking risks on their Common App. They play it safe because the stakes are $80,000 a year and their entire future. UChicago is the one place where playing it safe is actually the riskiest thing you can do. A boring response to a quirky prompt is a death sentence for an application.
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Breaking Down the "Uncommon Essay"
The University of Chicago essay usually consists of two parts. You have the "Why UChicago?" essay, which is standard but still requires a level of specificity that most schools don't demand. Then you have the legendary "Prompt 2," the creative one.
That Famous "Why UChicago?" Prompt
Most people mess this up by talking about the "vibrant campus" or the "distinguished faculty." Don't do that. Every school has a campus. Every top-tier school has famous professors. If you could swap "University of Chicago" with "Northwestern" or "Columbia" and the essay still makes sense, you’ve failed.
You need to mention specific things. Talk about the Core Curriculum. Mention the "Scav" (the world’s largest scavenger hunt). Talk about the fact that they have a house system that feels a little bit like Harry Potter but with more Milton Friedman. You have to prove that you actually want to go to this school, not just a top-ranked school.
Handling the Creative Prompts
The creative prompts change every year. In the past, they’ve asked students to invent a new holiday, explain why a hot dog is or isn't a sandwich, or discuss the "Alice in Wonderland" rabbit hole.
- Pick the one that makes you laugh. If a prompt strikes you as funny, you’ll write a better essay. Passion is hard to fake, but curiosity is impossible to hide.
- Don't overthink the "right" answer. There isn't one. If the prompt is "Where is Waldo?", they don't actually care about the guy in the striped shirt. They care about the concept of invisibility, or urban planning, or the ethics of surveillance.
- Show your work. UChicago loves the process of thinking. If you’re arguing something absurd, use logic to get there. It’s the "how" that matters, not the "what."
The Trap of Trying Too Hard to be "Quirky"
There is a very real danger in the University of Chicago essay process: the "Quirky Trap." This happens when a student tries so hard to be weird that they forget to be coherent. You see it every year. Someone writes an entire essay in binary code or tries to write a poem about a piece of toast that doesn't actually say anything about their personality.
Being different for the sake of being different is annoying. Being different because you genuinely have a strange way of looking at the world is brilliant.
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I remember an applicant who wrote about the "Middle." Not the middle of a sandwich, but the concept of the middle child, the middle of a story, and the "middle" as a political vacuum. It wasn't "weird" in a loud way. It was just deep. It showed that they could take a simple word and stretch it until it revealed something new. That’s what the admissions office wants. They want to see that you can handle complexity without getting lost in the weeds.
Real Advice for the 2025 Cycle
If you are sitting in front of your laptop right now staring at a blank Google Doc, stop. Just stop. You cannot force a University of Chicago essay. It has to come from a place of genuine interest.
Go for a walk. Read a Wikipedia article about something you know nothing about—like deep-sea hydrothermal vents or the history of the stapler. See where your mind goes. The best UChicago essays often start as a joke or a "What if?" conversation with a friend.
- Avoid the "Grand Reveal." You don't need a twist ending.
- Write like you speak. Well, a slightly more polished version of how you speak. If you use words like "heretofore" in real life, fine. If not, don't start now.
- Keep the focus on you. It’s easy to get so caught up in the topic (like the physics of a black hole) that you forget to put yourself in the essay. Every sentence should indirectly tell the reader something about your values or your intellect.
The University of Chicago is one of the few places that truly values the "misfit" intellectual. Their essay prompts are a gift, honestly. They are giving you permission to stop being a "perfect applicant" and start being a person.
The Specifics of "Option 6"
For those who don't know, UChicago always includes an "Option 6" which basically says: "Make up your own prompt."
This is the ultimate power move.
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However, it's a double-edged sword. If you choose your own prompt, it better be better than the ones they provided. Usually, students use this to recycle a particularly strong creative essay they wrote for another school or a contest. That's fine, but make sure it fits the UChicago "vibe." If it feels like a standard "discuss a challenge you overcame" essay, don't use it. They want spice.
Actionable Steps for Your Final Draft
You've written the draft. Now what? You need to audit it for what I call "The UChicago Filter."
Check your opening sentence. Does it hook the reader immediately? "I have always been interested in history" is a snoozer. "My history teacher is a ghost" is a hook. (Don't use that specifically, but you get the point.)
Look for "The Pivot." Somewhere in the middle of your creative essay, you should pivot from the abstract topic back to your own life or thinking process. If you're talking about the color blue for three pages, eventually you have to explain why the color blue matters to you.
Kill the clichés. If you find yourself writing about "stepping out of your comfort zone" or "learning a valuable lesson," delete it. Those phrases are the death of creativity. Use specific, sensory details instead.
Read it out loud. This is the oldest trick in the book because it works. If you stumble over a sentence, it's too long. If you get bored reading your own work, the admissions officer—who has 50 more essays to read before dinner—definitely will.
The University of Chicago essay isn't a hurdle; it's an invitation. If you treat it like a chore, it will read like one. If you treat it like a playground, you might just find yourself moving into a dorm in Hyde Park next fall.
Next Steps for Success
- Read past successful essays. Sites like "The Choice" (NYT) or even Reddit’s r/ApplyingToCollege have archives of successful UChicago essays. Don't copy them, but use them to understand the "level" of thought required.
- Research the "Core." Understand the Core Curriculum deeply. It informs the way UChicago students think, and referencing that style of interdisciplinary thought in your essay can show you've done your homework.
- Find a "Devil’s Advocate." Give your essay to someone who doesn't know you well. Ask them what kind of person they think wrote it. If they describe someone you don't recognize, go back to the drawing board.
- Check the "Uncommon" Prompts regularly. They often post them in late summer. Getting a head start on brainstorming is the only way to avoid the October panic.