ORD got some decent rain today, but MDW did not (only 0.04" there).
This brings me to tomorrow and my thoughts on hitting 100F in Chicago. ORD is the official observation site of course, but we pay attention to MDW too.
850 mb temps in the mid 20s C and mixing to that level would support 100F temps, but the issue is that progged mixing heights look to be a bit below that level. Based on this being such a marginal setup to begin with, today's rains, and temperature performance at ORD so far this warm season, I do not believe that ORD has a meaningful chance to hit the century mark tomorrow.
MDW is a more interesting one. Given the lack of recent rain and it tending to run warmer than ORD, I believe there's a shot of touching 100 there... I'd give it maybe about a 40% chance at this point. Here's some "benchmark" temps that I'd want to see if MDW is to have a good chance of triple digits:
10 am: 89
Noon: 95
2 pm: 98
These are not hard rules, and failure to meet those marks wouldn't necessarily preclude a high of 100, but I think it's a pretty good guideline of target numbers to try to reach.