@hs2020dad Welcome to the University and the Hyde Park/Kenwood/North Woodlawn neighborhood. I am in Hyde Park right now and I am quite familiar with this area.
There are two links that you and your first year should start with:
https://maps.uchicago.edu
https://safety-security.uchicago.edu/transportation/
The first one will tell you where the major academic buildings are. The second one will tell you how to get around.
Generally speaking, the University of Chicago like many of her urban peers is located within a very secure bubble. Roughly speaking, you are safe in the general area from 47th Street to 63rd Street and from the lakefront all the way to Cottage Grove Avenue. Within the actual campus of the University, you are exceedingly safe. I have no problem of walking alone at 3 am inside the Main Quad. And this being U of C, you may find students walk to and from Reg (Regenstein Library) literally at any time of the day.
All the horror stories you hear about Chicago street violence are unfortunately true. But they all happen OUTSIDE the Hyde Park/Kenwood/North Woodlawn community. Depending on your political inclination, you may find reassurance in the fact that U of Chicago Police Department (UCPD) is the second largest police force in the entire State of Illinois. The double presence of UCPD and CPD provides the much needed security that is essential for the survival of the University amidst the urban slums surrounding it.
I had lived in Hyde Park many years ago when crime was much worse. Now I feel safe walking around in areas that I wouldn’t dream of doing so thirty years ago. Indeed one fairly common compliant from the nearby communities is the gradual expansion of the University and the gentrification of neighborhoods as well as the displacement of long time local residents. Nowadays many students routinely walk across Midway Plaisance in the wee hours of the morning without any fear. Along 59th Street and many busy spots inside the University there are security guards standing there 24/7 365 days per year (except during Polar Vortex a few years ago when the windchill dropped to minus 45 degree).
Under the Getting Around tab you will the University Shuttle link. The primary buses for students are UGo Shuttles. UGo Shuttles have Day route and Night Route. Depends on which dorm you kid ends up in, you may want to study the Shuttle Map so that he knows where he can get on the bus and where he can get off.
My guess will be for most 1st Year they will not be doing much cooking. I like Hyde Park Produce for their fresh veggies. But it is out of the way at 53rd for most students living in dorm. Jewel Osco (of the national supermarket company Albertson) is the largest grocery chain in Chicagoland. The store at 61st and Cottage Grove was opened 18 months ago and provides a much needed full fledged supermarket in the community. It is very safe to shop there (and the tough looking and armed security guard standing by the entrance probably helps ).
Because of COVID, the usual orientation excursions to downtown or beyond are likely curtailed. U of Chicago campus is relatively small. Most students would walk between campus buildings during normal school hours. And with a significant portion of classes being online, honestly I think in the first couple of months your kid will likely just stay in Hyde Park. And that will give him plenty of time to adjust to city life.