Should I send a letter of interest to the University of Chicago waitlist, and what should it include?

Yes, sending a waitlist letter of continued interest to UChicago is usually worthwhile, especially if UChicago is one of your top choices and you have something concrete to say. The key is to send one strong letter, not multiple casual check-ins.

Your letter should do three things. First, clearly state that you want to remain on the waitlist and, if true, say that UChicago is your first choice or that you would enroll if admitted. Second, give meaningful updates since you applied, such as stronger grades, a new award, a leadership role, a research or project milestone, or a notable accomplishment. Third, explain specifically why UChicago is still a fit, using details that are distinctive to the school rather than generic praise.

For UChicago, the best school-specific reasons usually connect to its Core Curriculum, emphasis on discussion and inquiry, undergraduate research, or a program, institute, class, or student publication that genuinely matches your interests. Avoid vague lines about loving the campus or wanting a rigorous education, since those could apply to many colleges. A concise letter that sounds informed and sincere is much better than a dramatic or overly polished one.

Keep it to about one page. If you have no real updates, you can still send a short letter reaffirming interest and giving one or two specific reasons UChicago remains compelling, but it will be stronger if it includes new information.