I would never take the risk of trying to arrive same day for such an important onward connection on a non-Southwest flight.
Especially with things so screwed up with the Max8 situation. Too many moving parts. Flights get cancelled and delayed all the time.
On top of that, during summer thunderstorm months? No. Flying ex-MDW, I have plenty of experience with that.
Go the day before, stay the night, and relax.