Chicago Essay Questions

The University of Chicago’s essay prompts get a lot of attention, and rightfully so.  They are typically some of the most interesting and thought provoking that an applicant will encounter.  When I was an admissions officer at the University of Chicago, I would regularly hear from applicants that part of the reason they applied was those essay prompts—they couldn’t wait to grapple with them.  By contrast, in my later life as a high school counselor, I’d hear from some students, “I don’t want to apply there—those essays look too hard!”  Clearly, the essays are serving their purpose for the admissions office by attracting the right students, those who find Chicago’s eccentric brilliance (cough, nerdiness!) to be a match for their own spirit.

So let’s dig into the essay questions themselves.  First, just like all supplemental essays at schools which read applications holistically, the Chicago essays should be understood as  puzzle pieces that form part of a whole.  Each essay fulfills a different part of the application, and each is important. 

With that in mind, let’s look at the first question, a required question:

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 question is very important.  As with all schools, students are expected to have done their research on Chicago and what makes it unique.  This is perhaps even more important when it comes to Chicago, however, as it does possess a more unique identity than most schools in the U.S.  When answering this question, consider whether the intense intellectualism of Chicago’s student body and Chicago’s core curriculum, the cornerstone of each student’s academic experience, is right for you.  This question will best be answered seriously and straightforwardly by most applicants.

While the second question is optional, most students answer it.  This prompt reads:

Share with us a few of your favorite books, poems, authors, films, plays, pieces of music, musicians, performers, paintings, artists, blogs, magazines, or newspapers. Feel free to touch on one, some, or all of the categories listed, or add a category of your own.

When I worked at Chicago, this question was a fun one to review.  As the question permits, some applicants would list favorites from all categories, some from just a few, and some would just list one.  Others, instead of providing a list would explain a bit about the items they chose.  All of the above was fine!  This question was simply an interesting way to get a sense of a student’s interests and likes.

The extended essay questions are the ones that get Chicago all the attention, the ones that attract Chicago-like students to Chicago.  My best advice here is that you not try and guess which is the “best” topic or the topic the Chicago admission readers want you to answer, for there is no such thing.  Each topic they list is fair game, and it’s the applicant’s job to figure out which one will allow her to express herself best.  Some topics are clearly tongue-in-cheek, like this year’s first essay option: “Orange is the new black, fifty’s the new thirty, comedy is the new rock ‘n’ roll, ____ is the new ____. What’s in, what’s out, and why is it being replaced?” and the third: “Joan of Arkansas. Queen Elizabeth Cady Stanton. Babe Ruth Bader Ginsburg. Mash up a historical figure with a new time period, environment, location, or occupation, and tell us their story.”  If these grab you and your response to the prompt is humorous, go with it.  However, if your writing style is more naturally serious, you might want to try the other essay options.

Chicago also gives the option of posing your own essay question.  While this was certainly permissible and led to some great essays when I was a reader there, it was also where we saw students simply submitting essays that didn’t have the verve or interest of a “Chicago” essay.  Often we could tell that the student had simply pasted an essay there that he had written for another school.  I definitely don’t recommend doing that.  It can seem like a wise decision to make when you’re time-crunched and trying to get your applications done, but it isn’t really in the true spirit of the University of Chicago.

So, if none of this year’s topics speak to you, what are you to do?  Look to the final option and go to Chicago’s archives of questions.  There, you should easily be able to find one that speaks to you.  And you will still be true to the spirit of the Chicago application.

This is a prompt that appears every year. This essay really poses the highest risk but also the highest potential reward. Writing your own question allows you to write an innovative essay that either tackles a difficult or controversial topic (for example, our founder Vinay Bhaskara’s essay tackled why mainstream Hollywood films are more valuable than seemingly more intellectual independent films), or presents the information with a unique format (such as a conversation with a dead historical figure).


Using a prompt from past years also allows you to write an essay that is thematically and tonally different from many other applicants (as they will mostly be writing about the first five prompts offered above).


Generally speaking, your best payoff to this essay comes if you want to try something unconventional, such as writing an essay that describes the four years of high school as Hell, Purgatory, Paradise, and Heaven, and is written in the style of the divine comedy.


There are a variety of possibilities here ranging from the idiotic (you probably don’t want to write your own variation on the alt-right’s platform referring to events in your high school life) to the (relatively) overdone — they’ve probably seen several essays that have been written in iambic pentameter as an ode to Chaucer.


And we’ll reiterate the note above: This type of essay has the highest variance in terms of outcome. If done well, an unconventional essay can captivate the right admissions counselor in a way that no conventional essay can. Conversely, if the essay is executed poorly or even if it isn’t, your essay may go over the admissions counselor’s head or bore them. So this is only a strategy that you should try if you are confident in your abilities and have at least a couple of sources of high-quality feedback.


This is also an optimal prompt for truly diving into an academic passion, particularly if it is of an advanced level or unique tenor. For example, if you know a lot about Soviet cars produced between 1957 and 1983, then writing a custom prompt that allows you to explore that passion may be easier than trying to bend that topic to match one of the prompts provided.


As with any academically oriented essay, you do want to make sure that any jargon you use is made clear, either via explicit explanation or context clues. You shouldn’t shy away from jargon — it’s one of the things that helps position you as an expert on the subject of your essay. But you don’t want to render the essay unintelligible to your reader.


One broader note on writing your own prompt — it doesn’t have to be as complex or convoluted as the other UChicago prompts, and you mainly just want to find a prompt that matches the essay that you want to write, even if it is straightforward.


We wish you the best of luck writing your UChicago essay!


If you’d like assistance on your essay, learn about our essay editing program.

0 thoughts on “Chicago Essay Questions”


Leave a Comment

Your email address will not be published. Required fields are marked *