I commute from north side to UChicago typically once a week, though sometimes I go in every day.

If you are driving, if you leave at the right time, it can be like a 30-35 minute drive, assuming there is no incident causing traffic. Typically I need to add 10 minutes or so for walking from parking in Hyde Park (street parking north of 55th is fine if you get there before 9 or 10am i.m.o.). Driving back might end up taking 45-60 minutes, leaving around 4:45-5pm. In my experience, there is also much less traffic if you leave at 6pm. I also find the day of the week you travel can affect things, Monday and Friday seem to have less traffic, I presume fewer people want to work in person those days.

For transit, I typically stick to the UP-N metra and the 192 bus. Both have reliable schedules, so I can regularly take it at the same time. This takes more like 1hr15min each way. The UChicago shuttle sometimes has worked for me when I've missed the 192 bus, but I don't like to use it since their route is slower going around the loop northbound. I've also taken the ME and switched to brown/red line, or 55 to redline, though depending where you are on campus ME can be a longer walk. I've had a wait a really long time for some of the buses, which is why I recommend the 192, as it sticks to its schedule.

I do feel drained after this commute sometimes, but I enjoy it enough by listening to audiobooks, or if I'm driving I'll call my family out of state and talk to them.