Cushy Jobs

Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.

Virtual assistant jobs in Chicago, IL

Cushy WFH virtual assistant roles open to applicants based in Chicago, IL.

Most cushy virtual assistant 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 virtual assistant listings open to Chicago, IL applicants

Common questions about virtual assistant jobs in Chicago, IL

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