Safety schools are important, but if the OP chooses to ED0 to U Chicago and sends in their application early in the window, the notification date is so early (and rolling!) that they could wait until being notified before submitting other applications (even to meet EA or ED1 deadlines). Safetyish schools typically have simple enough applications that OP could choose them and put together applications in October, if denied from UChicago.
From https://summer.uchicago.edu/pre-college/admitted-students/ssen/
Eligible students may apply using this option from September 1 to October 15, and will receive an admissions decision three weeks (or prior to November 1) after completing their full application during this time frame.