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How to Respond to the 2023/2024 University of Chicago Supplemental Essay Prompts

By Cece Gilmore

Cece Gilmore is a Content Writer at Scholarships360. Cece earned her undergraduate degree in Journalism and Mass Communications from Arizona State University. While at ASU, she was the education editor as well as a published staff reporter at Downtown Devil. Cece was also the co-host of her own radio show on Blaze Radio ASU.

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Reviewed by Bill Jack

Bill Jack has over a decade of experience in college admissions and financial aid. Since 2008, he has worked at Colby College, Wesleyan University, University of Maine at Farmington, and Bates College.

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Edited by Maria Geiger

Maria Geiger is Director of Content at Scholarships360. She is a former online educational technology instructor and adjunct writing instructor. In addition to education reform, Maria’s interests include viewpoint diversity, blended/flipped learning, digital communication, and integrating media/web tools into the curriculum to better facilitate student engagement. Maria earned both a B.A. and an M.A. in English Literature from Monmouth University, an M. Ed. in Education from Monmouth University, and a Virtual Online Teaching Certificate (VOLT) from the University of Pennsylvania.

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Updated: November 2nd, 2023
How to Respond to the 2023/2024 University of Chicago Supplemental Essay Prompts

Chicago isn’t only known for its deep dish pizza. It is also famous for being home to the prestigious University of Chicago, which has an acceptance rate in the 6% range. So, let’s learn how to make your UChicago supplemental essay question responses stand out! Applicants must complete two UChicago supplemental essays. To make your responses perfect, complete some research before! Figure out what it is about UChicago (besides deep dish goodness) that makes you want to attend their school! 

The University of Chicago is also famous for having some…unique supplemental essay questions. So, put on your creative cap and get ready to have some fun while responding to UChicago’s supplemental essay questions. Here’s our guide for how to ace these creative UChicago supplemental essays!

Also see: How to write an essay about yourself

Essay question #1 

“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 is your typical “Why us” essay. However, do not make your response boring or universal! Make it specific to UChicago. Use this space to really detail why this school is the perfect fit for you. 

Explore both the academic and extracurricular aspects of the university that stand out from others. Maybe you are extremely passionate about majoring in biology to soon become a doctor one day. Therefore, discuss what courses, research, and study abroad opportunities UChicago has to offer that will make this goal attainable. It is important to touch upon what you want your future to look like and how UChicago will get you to reach all of your goals. It is also important to touch upon the aspects of their school that makes them unique. What makes UChicago stand out from all of the other schools you are considering? 

Overall, an admissions officer reading your essay should have a good sense of what you are looking to get out of UChicago. In addition, they should easily be able to see how much research you have done and how serious you are about attending their university. 

Questions to consider

  • What makes UChicago unique from other colleges? 
  • Why are you excited to attend UChicago? 
  • Why did you choose to apply to UChicago? 

Also see: How to write a 500 word essay

Essay question #2: The extended essay

For the extended essay portion of your application, UChicago provides applicants with seven unorthodox essay options. Each of these choices were created by UChicago alumni and students, which means these questions were made with you in mind. They also emphasize creativity and unique ideas when responding to these prompts, so try to have fun with them! 

Option #1

“Exponents and square roots, pencils and erasers, beta decay and electron capture. Name two things that undo each other and explain why both are necessary. -Inspired by Emmett Cho, Class of 2027” 

This is a question that requires your thinking hat to be on to answer it! To begin, just brainstorm! Try to come up with some ideas of 2 things that undo each other, bonus points if you can come up with something that has significance in your life such as something you use on a daily basis or something you are passionate about. For example, if you want to major in chemistry at the University of Chicago, discussing beta decay and electron capture could reveal your passion for the subject. However, no pressure if you can only think of something logistical rather than meaningful to you! Once you are satisfied with your idea, you should describe how these 2 things undo each other and why both are necessary. Ultimately, this question is trying to hint at how balance is important! You should try to use this prompt as a way to dig deeper into your life and reveal some aspects of your personality and thought-process. Below are some examples of things that undo each other in case you are completely stuck! 

Some examples of things that undo each other: 

  • Typos and autocorrect
  • Wetness and a towel
  • Addition and subtraction
  • Lock and key
  • Sewing and unthreading
  • Stains and laundry 
  • Photosynthesis and cellular respiration

Questions to consider:

  • What 2 things do you use in your daily life that undo one another? 
  • Do you believe that balance is necessary in life? 
  • Why do you think so many things in our lives undo each other? 

Option #2

“”Where have all the flowers gone?” -Pete Seeger. Pick a question from a song title or lyric and give it your best answer -Inspired by Ryan Murphy, AB’21”

If you love music this is the perfect option for you! Think of your favorite singer, song or band and find a title or lyric that asks a question. The creativity with this prompt is endless, you can select a deep philosophical question or just an easy-to-answer funny question. Ultimately, what matters is that you answer the question in a creative and meaningful way. You want your unique personality to shine through throughout this response so be sure to be yourself in your writing. Below are a few examples of questions found in song titles or lyrics! But, feel free to select a question from a song that means a lot to you. The choice of lyric and singer can reveal a lot about your personality. 

Example of questions from song titles or lyrics:

  • “Should I stay or should I go?” -The Clash
  • “What would you do if you weren’t doin’ this?” -Luke Combs
  • “Wouldn’t it be nice?” -The Beach Boys
  • “Do you believe in magic?” -The Lovin’ Spoonful
  • “If the story’s over, why am I still writing pages?” -Taylor Swift
  • “What if I’m someone I don’t want around?” -Harry Styles
  • “What’s love got to do with It?” -Tina Turner
  • “Should I give up or should I just keep chasin’ pavements even if it leads nowhere?” -Adele

Question to consider:

  • What is your favorite song title or lyric that asks a question?

Option #3

“Vlog, Labradoodle and Fauxmage. Language is filled with portmanteaus. Create a new portmanteau and explain why those two things are a “patch” (perfect match). -Inspired by Garrett Chaflin, Class of 2027”

Language is fun due to the unique creative word mashups that can be made. So, put on your creativity hat and think about two words that just need to be combined! This question is specifically asking for a “new portmanteau” so do not use a common portmanteau! Rather, try to be extremely creative in coming up with your patch (perfect match)! However, try not to forget that this is an essay to help you become admitted to the University of Chicago! Therefore, try to take it one step further and create a portmanteau that uses 2 words that describe you or one of your passions. Using words that are aspects of your identity can reveal so much about yourself which is all the University of Chicago wants from your response! 

For example, maybe you choose the words “runner” and “scientist” to make “runnitist” to describe yourself because you love to run but love to focus on the science behind running and training to avoid injury and be the best runner you can be! This can also lead you to discuss how you want to become a physical therapist and that is why you want to attend the University of Chicago! See full circle! Or should we say furcle?

Examples of common portmanteaus:

  • Smog (smoke and fog)
  • Brunch (breakfast and lunch) 
  • Spork (spoon and fork)
  • Motel (motor and hotel)

Questions to consider:

  • What are 2 words used to describe yourself? 
  • Why do you think these 2 words fit so well together? 

Option #4

“A jellyfish is not a fish. Cat burglars don’t burgle cats. Rhode Island is not an island. Write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept -Inspired by Sonia Chang, Class of 2025, and Mirabella Blair, Class of 2027”

Misnomers are a fun (or confusing) part of language. Therefore, spend some time researching and brainstorming some misnomers. Once you find one that you love (or hate) you should begin crafting your response. Ultimately, it does not matter if you decide to change the name or keep it, rather your argument should be prioritized. Your argument will show admissions how your brain works and disclose what you are passionate about. Therefore, focus on crafting a strong and persuasive argument that supports your reasoning, no matter how ridiculous this argument may seem! 

Examples of misnomers:

  • Koala bears = they are marsupials not bears
  • Light-year = a measure of distance not time
  • Silkworm = they are caterpillars not worms
  • Black boxes = they are bright orange not black
  • Centipedes = they do not have 100 legs rather it varies from 30 to 354

Questions to consider:

  • Should your selected misnomer name be kept? Why or why not?
  • Are misnomers confusing? 

Option #5

“Despite their origins in the Gupta Empire of India or Ancient Egypt, games like chess or bowling remain widely enjoyed today. What modern game do you believe will withstand the test of time, and why? -Inspired by Adam Heiba, Class of 2027”

If you love game nights this is the prompt for you! Try to brainstorm some modern games which are games that are not considered classics such as checkers. Rather think of some recent games that have swept the newer generations such as mobile phone games or beach games such as Spikeball. Once you have decided on the perfect game that you believe will withstand the test of time, write about it! However, it is important to remember that the University of Chicago wants to know about you- not about a game! Therefore, try to limit your time explaining the game’s rules and intricacies! Rather, focus on how the game makes you feel or why you think games are important to society. Ultimately, be sure you are revealing unique qualities you demonstrate throughout your response!

Examples of modern games:

  • Candy Crush
  • Hay Day
  • Dungeons and Dragons
  • Uno
  • Spikeball

Questions to consider:

  •  What is a modern game you feel will withstand the test of time?
  • Why do you enjoy playing this game? Do you like that it’s a single player game? Teamwork game? Strategy game? 
  • Why is playing games important for society? What benefits does gameplay have? 
  • Has this game taught you anything? Any important life lessons? Any new skills? 

Option #6

“There are unwritten rules that everyone follows or has heard at least once in their life. But of course, some rules should be broken or updated. What is an unwritten rule that you wish didn’t exist? (Our custom is to have five new prompts each year, but this year we decided to break with tradition. Enjoy!) -Inspired by Maryam Abdella, Class of 2026”

If you have ever been curious about some quirks of human life then this is the prompt for you! Try to think about an unwritten rule that has bugged you for a while. Why does this rule bother you? Why do you think people follow this rule even though it is unwritten? After you explain the rule and your side you should focus on shifting your response to reveal more information about your interests, goals and character.

Examples of unwritten rules:

  • Saying hello to fellow hikers on a trail
  • Asking people at tourist locations where they are from
  • Knock on the door before entering
  • Offering guests to your home a beverage or food
  • Don’t swipe on someone’s phone when they show you a picture
  • If someone is treating you to lunch, do not order the most expensive menu item

Questions to consider:

  • What is an unspoken rule that has always confused you? 
  • How does this rule make you feel? 
  • Why do you think this rule has been unspokenly accepted? 

Option #7

“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!”

This prompt is your chance to create something completely new and unlike any other application UChicago has ever received. Use your creativity to the fullest extent and figure out your own way to showcase your personality. However, make sure you don’t go too overboard and stay focused on your goal of getting into UChicago. 

Try not to make your essay revolve around your academic achievements. Instead, tell a story of how you’ve grown and what led you to UChicago’s doorstep, or describe an old proverb and how it relates to your life. Either way, your options are unlimited and making your own prompt demonstrates your interest in attending this university. 

Questions to consider:

  • What story do you want to tell the admissions office?
  • How can I best showcase your knowledge or skills?
  • What are some of the older UChicago prompts that caught your eye?

Next steps after applying to UChicago

Now that the fun is over, and you have completed your UChicago supplemental essays – it is time to celebrate! Treat yourself to some deep dish pizza because you are one step closer to the Windy City!

Now, continue to show that you are interested in the university! You can do this by following their social media accounts, scheduling a tour, and reaching out to their admissions officers. Doing any of these will prove you are willing to take the next step with UChicago. 

After you have proven your interest in the school, time to sit back and relax! All the hard work is over. Soon enough, you will be relaxing in a dorm that overlooks the city skyline of Chicago. 

Additional resources

We know that being a student applying for colleges is not easy. There are a lot of tough choices that need to be made when it comes down to selecting a college. Once you start hearing back from colleges you should use our college comparison spreadsheet to help you. You can also check out our guide to how many schools to apply to in order to ensure you’ve got yourself covered.

In addition, be sure to check out our free scholarship search tool to help you choose a financially smart educational institution! It is always important to consider finances when selecting a college. Good luck on your college journey! Remember you will always end up where you need to be! 

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Additional colleges to consider

Frequently asked questions about the University of Chicago supplemental essay prompts

How should I approach brainstorming for the University of Chicago essays?

You should begin by jotting down your initial thoughts and reactions to the prompt. Let your mind wander and consider different angles and perspectives on the topic! 

Can I reuse my Common App personal statement for one of the supplemental essays?

No, we would not recommend doing so. Rather, you should tailor each essay response to address the specific question or prompt. This will show that you’ve put thought into your responses and that it is specific to the University of Chicago. 

When are the application deadlines for the University of Chicago?

Application deadlines for the University of Chicago can vary depending on whether you’re applying for Early Decision or Regular Decision. Make sure to check the university’s official website for the most up-to-date information! 

Can I get creative with my University of Chicago supplemental essay answers?

Yes! The University of Chicago chooses extremely unique and creative questions in order to see the creative side of their applicants. So, try and answer the second essay question as creative and outside-of-the-box as you possibly can! 

Related: When Should I Apply to College?

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