As others have said, take a MOOC as a refresher. Don't sweat it. Just spend an hour a day on it, and maybe sit down with it for 4 hours on the weekend. You can do that -- just start today.
You have experience as a Java developer, and I don't know about Chicago specifically but I would wager that's half of all jobs there. Java has changed since then, but I'm reasonably sure it's all syntactic sugar and neato new features than you can mostly learn in a few hours of study.
The only real hard parts are:
1) Getting your shit and your resume together, and determining the narrative you're going to tell people. Try to make your time in entertainment as exciting and creatively fulfilling, that you were chasing a "dream." Talk about how strong you are with interpersonal skills and everything you've learned from the experience. Give them the impression you're ready to buckle down again and get serious. The right hiring manager will understand and perhaps envy you.
2) Facing all the interview rejection. But remember, you just need to get your first job. The next one after that will be easy.
I wouldn't suggest taking pricey courses since everything is available for free, unless you have more financial resources than you indicate (e.g. have rich parents willing to pay for it or something).
Here's a course for you:
If it turns out it's too advanced (you might need more recent web experience), find another one and do that. Just an hour every day.
You've got this.