Chicagoan here as well. XXX Racing-Athletico puts on a practice crit series that starts in April and goes through June on Tuesday nights at LaBagh Woods. Cat 5 racers can earn race completion points even though its an open format. I’d recommend that to build bike/pack skills with in addition to your weekend races.
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Yeah, I agree strongly with this – rather than entering a full-fledged crit as your first race, a practice crit would be a great start. There will be first timers, juniors, masters, etc, all out there on the field, so you can fall in with people of your own speed and skill. There’s also no chance of being pulled and it’s totally okay to take a couple laps rest, then try to get back on and hang with the pack.
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Came here to say this. 
Check out if your area has any mentorship programs too! They will coach you some and you can earn points toward an upgrade just by doing the clinic. Good luck out there!
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Another thing I might recommend is working on your position on the bike. Get as low as possible and get comfortable putting out power in the drops. 28 weeks is a long time to prepare you for that.
On my very first crit, my normalized power on the first two laps was around 350w (my FTP was nowhere near 350w). I got dropped after a few laps.
I later saw myself on someone else’s Youtube video and I looked like a sail compared to all the fast guys. I was practically upright.
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I’m looking forward to doing the LaBagh Woods practice crits next year, it’s been on my to do list for a while now. I’ve done a few of their Saturday training rides as well.
Thanks!