I hear you. Supposedly travel demand is currently way down from 9/15-12/15. So fingers crossed no flight cancellations. I returned from Ireland 5/5 with no issues. I believe it was about two weeks later that travel went crazy including Dublin airport.
Midway by far. Easy to get out of and closer to ND. The other airport takes a long time to get out of and traffic is horrible. Lived you there for 40 years never would I use ohare. Hotels depends on what you want to do
They are both good options. You can Uber, taxi, or train to your hotel. O'Hare is on the Blue Line and Midway is on the Orange Line. O'Hare is currently in the middle of big construction and can be more of a pain for drop off these days. It is also the larger airport and has more options for food and drink. SWA recently added service to O'Hare (they've been at Midway forever), but their gates are in the International Terminal, which is off on it's own. I've been sticking with SWA out of Midway so I can't really speak to that.
If you are picking up a rental car at the airport the drive to the loop is about a wash. As you move further north the drive shifts in O'Hare's favor. Just depends on where your hotel is located.