Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH content moderation roles open to applicants based in Chicago, IL.
Most cushy content moderation 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 content moderation listings open to Chicago, IL applicants
Wulf Werkstattausrüstung GmbH · Various
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Crossing Hurdles · Various
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Crossing Hurdles · Various
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Vaco by Highspring · Various
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TELUS Digital · Various
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Cypress HCM · Various
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Saleshead Recruiting · Various
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The Sage Group · Various
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LinguaSenseAI · Various
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Krieger MIS GmbH · Various
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Concentrix · Business
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ICUC · Various
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ICUC · Various
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Kiwimo-Product GmbH · Various
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Martell Media · Various
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Jobgether · Various
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everydays · Various
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Talentwert Digital Research Studio · Various
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RG&T Solutions · Various
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Foodiary GmbH · Various
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Ecoturn GmbH · Various
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Martell Media · Various
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TELUS Digital · Various
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Jobgether · Various
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Verified listings in this category pay a median of $19/hour, ranging from $14 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.
Most cushy content-moderation work today is benign — search-quality rating, AI training data labeling, LLM response evaluation. The minority involving distressing user-generated content (typical for social-media trust-and-safety roles) is clearly labeled in our listings and pays a premium of $4–$8/hr above standard. We exclude trust-and-safety roles handling CSAM, terrorism content, or gore from this category entirely; those are specialized roles with mental-health support requirements and shouldn't be sold as "cushy."
Yes — both are large publicly-traded AI data companies (Appen on the ASX, Telus on the NYSE). Pay is reliable when work is available, but project assignments are intermittent — you may go weeks between active projects. Both run rolling 1099 contractor programs in the US, no relocation, no minimum hours, no shift schedule. Glassdoor ratings hover around 3.4–3.6, reflecting the project-availability variance rather than pay reliability.