Health coverage after losing my job: marketplace or Medicaid? (Chicago)

I have 14 weeks left on my current insurance and I am comparing options. It has been a long 23 weeks. I do not want a gap in coverage. What did you choose and how was the process?

Thanks for writing this out. I went through something close to it 13 months ago, and it got easier once I kept a simple log of every call and form.

Keep everything in writing and save the confirmation numbers. It saved me later.