Gonna channel my inner Alek and throw out a 5 day call.
For Wednesday, I'll go 97 at ORD and 99 at MDW. Multi-model agreement on 850 mb temps around 23-24C with fairly good mixing, the precise details of which will matter. Although I didn't bite yet, I still feel like there's a reasonable shot of triple digits at MDW.
What I would want to see to seriously entertain the idea of 100 at O'Hare would be a more solid indication of deep mixing or a trend toward slightly warmer 850 mb temps. It's just not there, at least at this point. As of now, would have to bet on it coming up short, much to my chagrin.
On another note, Thursday morning could be very warm barring any interference from convection/outflow from the north.