I have signed up for the Run for the Animals, and am thinking about the others. Subject to change completely as I look at the rest of life. I want to run primarily 5Ks, but throw in a few other races to push me. I might change some of these to get into larger races where I will more people I can pace with. The Run for the Animals is big (over 1500 runners in the 5K) but I have not read about the others.
The Elmhurst race (July 21) is where I ran my last race eight years ago. Running it again, comparing times might be fun (or depressing). I chose the others largely because of proximity to home. Running this many races is so that I am constantly testing myself. The Spivey track workouts will do that in one way, but those are pure training, and times become less important. The races will be part training and part testing.
All goals are subject to change based on progress up until that point. They are aggressively set and may not at all reflect reality. However, to run a 20:00 5K by September 30, the pattern below makes sense.
Date - Name - Distance - Location - Goal
Sat Jun 02 - Run for the Animals - 5k - Wheaton - TDB
Sun Jun 10 - Commit To Be Fit - 5k - Downers Grove - 24:45
Sat Jun 16 - Fox River 5k - 5k - Batavia - 24:30
Sat Jun 23 - Celebrate Life - 5k - Carol Stream - 24:15
Wed Jul 04 - Great Western Freedom 4 - 4 M - St Charles - 31:00
Sat Jul 21 - Elmhurst Run for Hunger - 5k - Elmhurst - 23:00
Sat Aug 11 - Winfield Run - 5k - Winfield - 22:00
Sun Aug 26 - Windrunner - 10k - Wheaton - 45:00
Mon Sep 03 - St Petronille 5K - 5k - Glen Ellyn - 21:00
Sun Sep 30 - Morton Arboretum Fall Color 5K - 5K - Lisle - 20:00
source: Chicago Area Runners Association Race Calendar