Applying to the University of Chicago? Then you are in for a treat. The university requires responses to unique and provocative supplemental questions that are great fun to write. Although the first required question prompts serious reflection, a deep understanding of the university and its offerings, and evidence of your own intellectual journey, the extended essay that is also required invites quirkiness, whimsy, and originality. Even those students who choose to write a response with the utmost seriousness will find this second essay a wonderful opportunity to show the University of Chicago who you are. What’s more exciting than that?
Needless to say, these required supplemental essays also reveal how you write and how you think. Take them seriously. They are your chance to make what can seem like a two-dimensional application feel 3D.
The University of Chicago Supplements
Chicago requires two supplemental essays: one question all undergraduate applicants must answer, and a second, extended essay that offers applicants a choice of topics.
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.
Most application essay questions that expect serious answers, including this one, provide the trajectory of a strong response. Consider, for a moment, the progression the prompt recommends: what kind of learning environment and community suits you→what do you want to study→why is the University of Chicago the perfect place to achieve your goals →what might you do with your degree in the future and what impact do you hope to make.
The prompt’s word choice also offers clues. Notice how the following words indicate what you should include in your answer: learning, community, future, wishes, relate. The prompt also includes words that demand evidence: how, know, particular, specificity.
An effective essay will address the following:
- How you learn (learning)
- What kind of community would be a good fit (community)
- What discipline you want to study (learning)
- What you have done (coursework, research, civic engagement, school activities) that shows how you know what you want to study (know)
- Specific programs, courses, clubs, or opportunities unique to the university that will help you achieve your intellectual goals or ambition. Show you have done your homework and can provide examples (relate)
- How you hope to make an impact after you earn your degree (future)
TTA Top Tip: This is your “why us” essay. You need to show why the University of Chicago is the perfect place for you.
Question 2: Extended Essay (Required; Choose one)
This is where the University of Chicago gets creative. The essay prompts from which applicants can choose for this second supplement are derived not from the admissions officers but from students and alumni. As the admissions office explains, “Each year we email newly admitted and current College students and ask them for essay topics. We receive several hundred responses, many of which are eloquent, intriguing, or downright wacky.” This original approach to crafting prompts offers you an opportunity to write something that could only be written by you.
TTA Top Tip: Be careful not to be someone you are not just to sound impressive. If you do not feel comfortable writing a whimsical response, don’t; you run the risk of hitting the wrong note. Not comfortable being creative? That’s ok, be eloquent. Write in the style that reveals who you really are, not who you think the university wants you to be.
- Food for thought: How do thoughts eat?
Inspired by Ernest Leong, Class of 2026
- The James Webb Space Telescope, launched in 2021, utilized origami-inspired techniques to compactly store and deploy its sunshield in space. Choose an artistic practice and use its principles to propose an elegant solution to a problem.
Inspired by Akhil Korra, Class of 2028
- Sometimes metaphors get mixed up. For one reason or another, one could say, “we’ll burn that bridge when we get there” or “the world is your china shop”. Make up your own mixed metaphor. Explain how it could make sense, be understood, or even applied.
Inspired by Julia Nieberg, Class of 2029
- The Olympics have long celebrated the pinnacle of human athletic achievement. But what if they expanded to honor the mundane? Imagine a new Olympic event built around an everyday activity like speed dishwashing or competitive grocery bagging. How is it scored, officiated, and judged? Why is it a worthy addition?
Inspired by Ewan Smith, Class of 2028
- AI: Allen Iverson. NASA, or the North American Saxophone Alliance. Share a potentially confounding, comedic, or captivating example of MIA (Mistaken Identity of Acronym) and tell us its backstory.
Inspired by Jeeho Byun, Class of 2030
- 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!
Regardless of which prompt you choose, start with a strong hook. Be specific, use vivid imagery, and be yourself. This is your chance to show the university who you are and who you hope to become. Ultimately, they are assessing whether you are a good match for their community and programs.
TTA Top Tip: Don’t underestimate the importance of these essays. Give yourself plenty of space to plan your answers. Allow time to write, revise, and edit. Keep in mind that effective answers establish a claim, provide evidence, include reasoning, and capture the interest of your reader. A good rule of thumb? If you are bored writing it, your audience will be bored reading it.
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She began her career at Kent School as an English teacher, coach, dormitory faculty member, and assistant athletic director, developing a deep understanding of students both inside and outside the classroom. After earning her master’s degree from Northwestern University, she joined Westminster School, where she ultimately served as Director of College Counseling, guiding students and families through academic planning and highly selective admissions.
Kate later held senior leadership roles at Pomfret School and for 12 years at The Winsor School, where she oversaw grades 5–12 academics, supervised college counseling, conducted mock interviews, and helped shape institutional strategy.
Having worked as a teacher, advisor, college counselor, academic dean, and associate head of school, Kate understands how admissions decisions are made — and how to position students thoughtfully and authentically. Today, she focuses on what she values most: partnering one-on-one with young people to help them tell their stories with confidence and purpose.
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