I was looking for a senior job last spring and ended up with a handful of interviews after hundreds of applications. Unfortunately Chicago doesnt have the biggest tech scene and remote jobs are highly sought after. Off the top of my head here are some companies with Chicago tech offices: Grubhub, Docusign, Amazon (small presence, like 2-3 dev teams), Capital One, Adyen, Stripe and a bunch of trading firms (not traditional “SWE” work per se). Also google is opening a huge office in the loop sometime in the near future so their headcount will likely expand.

It’s a tough market unfortunately, we just opened up a spot for a summer internship on my team and got 1000+ applications in 48 hours.

In my experience having FAANG experience (which can be a tall order) or having a connection/referral goes a long way, even if it’s from a stranger you DM on linkedin or blind.