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

My family's coverage ended with the layoff and we have a prescription we cannot skip. I would rather hear the honest version than the polite one. I do not want a gap in coverage. How fast did coverage start?

Losing job-based coverage usually opens a special enrolment window, so check the deadline on the official marketplace site. I missed it by a day once and regretted it.