Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH bookkeeping roles open to applicants based in Chicago, IL.
Most cushy bookkeeping 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 bookkeeping listings open to Chicago, IL applicants
Raff Law, APC · Various
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Red Square Accounting & Tax, LLC · Various
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CFS · Various
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Do Good Multnomah · Various
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MIS Solutions · Various
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Trettmann Sportgeräte GmbH · Various
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Custom Projects & Homes · Various
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Small Batch Standard · Various
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Corporate Green · Various
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Vito Courtney & Associates · Various
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Rio Izakaya · Various
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ProAutomated Inc · Various
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Weiss & Thompson · Various
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Tucker Accounting Services · Various
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CFO Dental Partners · Various
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RIGHT ANGLE CONSTRUCTION · Various
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ProAutomated Inc · Various
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One Way Pet · Various
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Startchurch · Various
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ProAutomated Inc · Various
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Remote Job Network · Various
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Mana Maoli · Various
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Startchurch · Various
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Kiwi Recovery LLC · Various
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Verified listings in this category pay a median of $26/hour, ranging from $20 to $42/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.
No — bookkeeping is distinct from accounting. Most listings require QuickBooks proficiency (Intuit ProAdvisor certification helps significantly) but no CPA license. A CPA is required for senior accounting, tax preparation, audit, and controller roles — those pay $40–$70/hr remote, but the entry path is bookkeeping first.
Cleanup specialists (entry-level): $20–$26/hour. Expert bookkeepers (1+ year with the program or external experience): $28–$34/hour. Seasonal tax-prep volunteers from October to April get bonus pay and access to advanced training. Intuit covers ProAdvisor certification and pays for state-licensing exams when applicable.