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MDW is much easier in general to use than ORD so probably the best you can do is keep an eye on your flight status on the airline's app (Southwest I assume). Also would recommend downloading the TSA app if you haven't already since that has TSA wait times etc.
Also some info here: https://thepointsguy.com/news/flight-cancellations-government-shutdown/
I flew out of MDW last weekend. Flight was delayed about an hour but that was due to maintenance issues on incoming plane. The TSA precheck lines were fine. Standard TSA was pretty backed up however I don’t think it was anything unreasonable. Clear is pretty generous with the free trials if they want an additional power up. I’d say getting there an hour before boarding should be fine.
Rising Star
Midway is usually pretty easy / quick to get through security. I don't think anyone can tell you whether the shutdown will have any affect this weekend. Presumably it will re-open this week and one would hope that air traffic controllers and TSA agents will be back at work - but it may take some time until the back pay comes in and some people who might have had to take on some side work are able to be fully back. My completely uninformed opinion says have them give themselves an extra 20-30 minutes more than whatever they are normally comfortable with in terms of arriving at the airport.