Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH online tutoring roles open to applicants based in Chicago, IL.
Most cushy online tutoring 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 online tutoring listings open to Chicago, IL applicants
iLearning · Various
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TeachMe.To · Various
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The Colleges of Law · Various
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Brightest Owl Tutoring · Various
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Tutero · Various
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DataAnnotation · Various
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FindTutors · Various
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Brightest Owl Tutoring · Various
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We Connect Academy · Various
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Hire Feed · Various
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TUS Media · Various
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OpenEd · Various
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Saga Education · Various
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GFN GmbH · Various
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TeachMe.To · Various
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TeachMe.To · Various
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TeachMe.To · Various
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Marigold Prep · Various
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Learner Education · Various
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QMP Education · Various
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Learner Education · Various
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Larson Tutoring & Test Prep LLC · Various
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TeachMe.To · Various
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More Than Mere Shelter · Various
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Verified listings in this category pay a median of $24/hour, ranging from $14 to $60/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.
For most paid platforms, no — but a bachelor’s degree in any field is typically required. Cambly, which focuses on conversational English, only requires native English fluency.
Wyzant lets you set your own rate (most charge $30–60/hr). Tutor.com pays a fixed $11–17/hr. Outschool varies — popular K-12 teachers earn $30–80/hr by setting their own class prices.