Updated May 9, 2026
Cushy WFH insurance remote jobs roles open to applicants based in Chicago, IL.
Most cushy insurance remote jobs 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.
0 sample listings (real data lands with ingestion)
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.