Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH admin & clerical roles open to applicants based in Chicago, IL.
Most cushy admin & clerical 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 admin & clerical listings open to Chicago, IL applicants
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Timeline Optimization Group · Various
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Jacoby & Meyers Accident & Injury Lawyers · Various
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Careers In Travel | Destination Planners · Various
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ABS Kids · Various
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Hill's Lawn & Landscape · Various
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Boldly Premium Executive Assistants · Various
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Radiology Partners · Various
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Orchestrate Consulting Group · Various
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Verified listings in this category pay a median of $19/hour, ranging from $15 to $28/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.
Schedules meetings, prepares and formats documents, coordinates with vendors, manages travel bookings, handles light bookkeeping (expense reports, invoice tracking), and supports HR onboarding. Tools are typically Microsoft 365 (Outlook, Word, Excel, Teams) or Google Workspace, plus a project tool like Asana or Monday. Most days are 60–70% async work, 30–40% scheduled calls.
Some do — Public Trust is the most common requirement and takes 4–8 weeks after offer. Secret clearance takes 3–6 months. Many federal entry-level admin roles (GS-5, GS-6) require only Public Trust, which most US citizens with a clean background qualify for. Listings on USAJobs make clearance requirements explicit.