Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH insurance remote roles open to applicants based in Chicago, IL.
Most cushy insurance remote jobs are fully remote and US-eligible, so applicants in Chicago, IL qualify for the same listings as anywhere else in the country. We surface listings here that specifically prefer or list Chicago, IL in their applicant criteria, plus the broader US-remote pool.
Chicago is the historic insurance industry capital — Allstate is headquartered in the Chicago suburbs, and Aon, Zurich, and CNA maintain substantial Chicago-anchored remote claims and customer service teams. Central time zone makes Chicago particularly attractive for BPO customer service supporting nationwide clients — workers can cover both East Coast morning peaks and West Coast afternoon peaks. Conduent and Concentrix run major Chicago BPO operations.
No insurance remote openings showing for Chicago, IL right now — check back soon or set an alert below.
Verified listings in this category pay a median of $24/hour, ranging from $19 to $38/hour. Most fully remote roles pay the same nationally regardless of where you live.
Most are open to anyone in the United States. We surface Chicago, IL explicitly when employers list it as a preferred or eligible location.
For agent / sales roles: yes — typically a state P&C (Property & Casualty) license, sometimes life/health. Most major carriers (Allstate, Progressive, USAA) pay for your study materials, exam fees, and training time as a new hire — you don't pay for licensing yourself.
Licensed claims adjuster pays $24–$36/hr, a notch above general customer service ($19–$26). Both pay above the broader cushy WFH average. Licensed sales agents on commission can exceed $40/hr equivalent in good months but with quota pressure that cushy seekers often want to avoid.