Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH customer service roles open to applicants based in Chicago, IL.
Most cushy customer service 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.
24 verified customer service listings open to Chicago, IL applicants
RG&T Solutions · Various
Posted just now · ✓ Verified just now
val's services · Various
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Home Health Focus AI · Various
Posted just now · ✓ Verified just now
Casella Waste Systems, Inc. · Various
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Tactacam · Various
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Concentrix · Business
Posted just now · ✓ Verified just now
DataAnnotation · Various
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Pricebook Digital · Various
Posted just now · ✓ Verified just now
Gilder Search Group · Various
Posted just now · ✓ Verified just now
DataAnnotation · Various
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Akkodis · Various
Posted just now · ✓ Verified just now
Concentrix · Business
Posted just now · ✓ Verified just now
Resonance CX Partners · Various
Posted just now · ✓ Verified just now
TestHiring · Various
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DataAnnotation · Various
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Quince · Various
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Mosaic Talent Consulting · Various
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Department of Veterans Affairs · Various
Posted just now · ✓ Verified just now
Brenmar Associates · Various
Posted 7 days ago · ✓ Verified just now
Concentrix · Business
Posted just now · ✓ Verified just now
Destinee Travel · Various
Posted just now · ✓ Verified just now
Cyber Focus AI · Various
Posted just now · ✓ Verified just now
DataAnnotation · Various
Posted just now · ✓ Verified just now
Concentrix · Business
Posted just now · ✓ Verified just now
Verified listings in this category pay a median of $18/hour, ranging from $15 to $27/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.
Based on 1,438 verified listings on Cushy Jobs, remote customer service roles pay a median of $18/hour, ranging from $15 to $27/hour. Healthcare and insurance customer service tend to pay $1–3/hour above average.
No — about 31% of the listings we track explicitly say no prior experience is required. Most BPOs (Concentrix, TTEC, Sutherland) provide 2–4 weeks of paid training before you take live calls.