Chicago native here. If you’re going to be staying in the city it’s not really the loop you want to stay in but more like the River North/Streeterville Area. Basically right along the river there are some great hotels right along Wacker and just North of there.
Navy Pier is going to be opening soon. Of course everyone (not sure why) is infatuated by The Bean. You can walk along the Lakefront (longish walk) to the Field Museum, Shedd Aquarium and the Planetarium. Closer in is the Art Institute which is amazing. Museum of Science and Industry which for some reason I’m not sure if it’s fully open, but if it is the big thing they’ve been talking about is the Marvel display, is further south in hyde park. Some public transportation routes are ok, others eh. You just need to be aware of your surroundings really. Personally, I would take a ride share down there. If you want to take a bus then it is MLK bus most likely but on google directions (whatever it’s called) you can check which public transportation to take.
Parts of the Loops you still have to be careful. There are a lot of homeless that are more of a nuisance than anything but you still have to be alert. South Loop has some shady areas, as does West Loop but much of it has been regentrified quite nicely. If you fly into Midway there have been a lot of car jackings lately there and south as well so again just really need to be on high alert like anywhere though in my opinion.
That cemetery looks like it’s near Woodlawn. Woodlawn is probably a no, but I can’t tell how far from Woodlawn it is and you’re not far off the expressway to go there. Harold Washington our former Mayor is buried there. But, I would just do a search on crime statistics nearby to really know if it’s a place worth going to or not.
Maybe ask your sister in law what she knows.
Also jumping on what @njsue said, 100% if the Chicago Architectural Cruises are running, you should definitely do that. It is fantastic. My kids would get to go on that for their photography class every year and I last went on it about 25 years ago. Can’t say enough how amazing it is. There’s also a boat ride that you can take along the lake front and see the skyline. I can’t remember what it’s called …maybe something like seadog…my son used to love it…get that near Navy Pier. The Architecture Tour by the River.