A little background info on 100+ degree days for Chicago in case it becomes relevant...
There have been 65 such days since records began. In earlier years, the official observation site for the city was located downtown, which suggests that there would've been more 100+ degree days in earlier decades had the official site been located farther inland (less prone to lake breeze).
Conversely, with the move of the official observation site to Midway Airport and then to O'Hare as of 1980, it's possible that some 100+ degree days at those locations may not have been as hot downtown. Just some things to keep in mind.
Anyway, as said, there have officially been 65 days of 100+ for Chicago. Of those 65, only 6 of them have occurred on or before June 21, so all in all we are looking to accomplish something that is quite rare this Tuesday. By the way, all of the years that produced a 100 degree temp on/before 6/21 went on to produce at least 1 more, but would caution about small sample size.
Monthly breakdown of 100+ degree days for Chicago:
Jun: 14
Jul: 36
Aug: 11
Sep: 4