I made 50k (like 30k after taxes) over the last year due to my summer internship and work throughout the school year; it is definitely possible to meet your goal. However, you can’t do it with minimum wage jobs, you will need to be skilled at a specific discipline. What is your intended major?
Here are some basic run downs on how many hours you need to work:
Low-wage job: $15/hour means you will need to work about 3000 hours during the year to make enough money after taxes. For a 12 week summer internship at 40 hours/week, you will have 480 covered. This means you have 2520 hours left to do. Add 4 weeks of full-time work for winter and spring break, that brings you to 2360 hours left. Given that there are about 33 weeks in the UChicago school year, this means you will need to work nearly 70 hours a week during the school year to meet your target!
Good-wage job: $45/hour means you will need to work about 1000 hours during the year to meet your target. Summer internship + winter/spring full time work will bring you down to 360 hours remaining. This comes down to about 10 hours a week of work during the school year, which is manageable with a UChicago schedule.
Also, is 53k your total cost of attendance? If so, how much of it is actual tuition, and how much is for food/housing, travel, and other expenses? You can cut the latter part to half of what they estimate by moving off campus (during second year), and spending conservatively.