There is a lot of work at UChicago by that I mean school work. It would be very difficult to work more than a few hours per week. My son has a job for approximately 5 hours a week (flexible and relatively high paying but it’s federal work study which you would probably not qualify for) and it has been touch and go if he can keep that job. He chose to take hard classes and a full 4 course load when lots take 3 classes 1st quarter of first year. Renting books wouldn’t hep because a lot of the classes use the same books for multiple quarters. The dining plan for first years is $6000 per year. No other option. The only meal it doesn’t include is Saturday dinner so you would have to pay for that too.