Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH chat & email support roles open to applicants based in Chicago, IL.
Most cushy chat & email support 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 chat & email support listings open to Chicago, IL applicants
Quince · Various
Posted just now · ✓ Verified just now
NoGigiddy · Various
Posted 3 days ago · ✓ Verified just now
Didi Hirsch Mental Health Services · Various
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RG&T Solutions · Various
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Jobright.ai · Various
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ms consultpartner · Various
Posted just now · ✓ Verified just now
NoGigiddy · Various
Posted 3 days ago · ✓ Verified just now
WVSU · Various
Posted just now · ✓ Verified just now
Turtles · Various
Posted just now · ✓ Verified just now
Aisle and Abroad · Various
Posted just now · ✓ Verified just now
Positive Behavior Steps · Various
Posted just now · ✓ Verified just now
Embrace Software Inc · Various
Posted just now · ✓ Verified just now
ms consultpartner · Various
Posted just now · ✓ Verified just now
Aisle and Abroad · Various
Posted just now · ✓ Verified just now
Didi Hirsch Mental Health Services · Various
Posted just now · ✓ Verified just now
Agile Financial Systems · Various
Posted just now · ✓ Verified just now
CapeTalent · Various
Posted just now · ✓ Verified just now
1-800 Contacts · Various
Posted just now · ✓ Verified just now
Absorb Software · Various
Posted just now · ✓ Verified just now
Jack Henry & Associates · Various
Posted just now · ✓ Verified just now
OnlineJobs.PH · Various
Posted just now · ✓ Verified just now
Canvia · Various
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Empathy · Various
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Concentrix · Business
Posted just now · ✓ Verified just now
Verified listings in this category pay a median of $19/hour, ranging from $16 to $26/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.
Yes — well-designed chat-only roles never ask you to take voice calls. We tag every listing with whether phone work is required and only list this category page jobs where chat or email is the sole channel. A small subset of listings labeled "omnichannel" expect occasional phone backup; those are filed under customer service, not here.
Most ask for 40–50 WPM minimum, with 95%+ accuracy. Tools like Intercom, Zendesk, and Help Scout auto-suggest replies and offer canned-response macros, so practical chat speed feels lower than raw typing. Email roles are slower (one well-crafted reply every 5–8 minutes) and weight clarity over speed.