Still a bit out there, but we are getting close enough to be able to dive into some specifics.
I'd say there could be a couple shots to approach the all-time record low at ORD. The first coming on Wednesday morning, which is more of an advective driven cold at that point with a bitter airmass aloft and winds staying fairly elevated. Then another one potentially coming on Thursday morning after having an extremely cold starting point Wednesday evening. Overall, Wednesday night/Thursday morning certainly looks like a better radiational cooling setup than Wednesday morning, though even then it appears the winds may not completely die off especially in/around the city. Also, the airmass aloft looks like it will be warming by late Wednesday into Thursday, so not having full decoupling could be a problem.
I'm still not ready to predict an all-time record low for ORD, but to me, if it happens, the better chance of it occurring is on Wednesday morning because that is when the radiational cooling component is minimized, and anybody who pays attention knows that ORD can have problems with radiating. That being said, Thursday can't be ruled out due to what was mentioned above about the extremely cold starting point.
Just my 2 cents and thoughts subject to change.