Updated June 25, 2026 · Insurance HQs + central-time-zone customer service.
Cushy WFH transcription roles open to applicants based in Chicago, IL.
Most cushy transcription 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 transcription listings open to Chicago, IL applicants
Mercor · Various
Posted just now · ✓ Verified just now
Medical Transcription Service · Various
Posted just now · ✓ Verified just now
Western Canadian Place Fitness Centre · Various
Posted just now · ✓ Verified just now
HireArt · Various
Posted just now · ✓ Verified just now
Mercor · Various
Posted just now · ✓ Verified just now
CrowdGen by Appen · Various
Posted 21 days ago · ✓ Verified just now
Alignerr · Various
Posted just now · ✓ Verified just now
Crossing Hurdles · Various
Posted just now · ✓ Verified just now
Mercor · Various
Posted just now · ✓ Verified just now
CrowdGen by Appen · Various
Posted 21 days ago · ✓ Verified just now
Allegis Transcription · Various
Posted just now · ✓ Verified just now
NTW Solutions Limited · Various
Posted just now · ✓ Verified just now
GMR Transcription Services, Inc. · Various
Posted just now · ✓ Verified just now
FWI (FedWriters, Inc.) · Various
Posted just now · ✓ Verified just now
CrowdGen by Appen · Various
Posted 21 days ago · ✓ Verified just now
Alignerr · Various
Posted just now · ✓ Verified just now
Wellstar Health System · Various
Posted just now · ✓ Verified just now
University of Southern California · Various
Posted just now · ✓ Verified just now
Ascendion · Various
Posted just now · ✓ Verified just now
eScribers, LLC · Various
Posted just now · ✓ Verified just now
CrowdGen by Appen · Various
Posted 21 days ago · ✓ Verified just now
CrowdGen by Appen · Various
Posted 21 days ago · ✓ Verified just now
CrowdGen by Appen · Various
Posted 21 days ago · ✓ Verified just now
GMR Transcription Services, Inc. · Various
Posted just now · ✓ Verified just now
Verified listings in this category pay a median of $17/hour, ranging from $12 to $35/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.
General transcription pays $0.30–$1.10 per audio minute, working out to $9–$25/hr depending on speed. Medical transcription pays $22–35/hr but requires certification.
No — Rev, TranscribeMe, and GoTranscript all hire entry-level transcribers after passing a short test (typically 5–10 minutes of audio).