Felony‑Friendly Jobs & Reentry Toolkit for Chicago & Cook County

Purpose: A practical handbook for justice‑impacted job seekers in Chicago and suburban Cook County—covering felony‑friendly employers, transitional jobs, training, record relief, and how to apply, with verified contacts.

Updated: December 11, 2025

Quick 5‑Step Path to Your Next Job

Connect with a reentry employment program:
- Chicago Cook Workforce Partnership (American Job Centers): career coaching, training, and direct employer links (1 N. Dearborn St., Ste 750; site, programs). ^[1][2]
- Safer Foundation: specialized placement for people with records; downtown office at 571 W Jackson Blvd; (312) 922‑2200. ^[3][4]
Apply for transitional or second‑chance work:
- City of Chicago DFSS – Transitional Jobs for Returning Residents: paid, time‑limited jobs + coaching; operator locations and phone numbers listed on the City page. ^[5]
- CTA Second Chance Program: holistic paid work and training; apply via partner referral (Cara, Safer Foundation, St. Leonard’s, St. Sabina, Westside Health Authority). ^[6]
Leverage statewide tools:
- IDES Re‑Entry Employment Service Program (RESP): job prep, IllinoisJobLink.com, and employer incentives (Fidelity Bonding, WOTC). ^[7]
Clear or mitigate your record (in parallel):
- CGLA Expungement/Sealing Help Desks (Daley Center Room 1006; Markham Courthouse Room 102J) + RAP sheet guidance. ^[8][9]
- Certificates of Good Conduct & Relief from Disabilities (OSAD forms & how‑to). ^[10][11]
Use verified directories:
- Illinois DHS Reentry Resource Hub. ^[12]
- CareerOneStop Reentry Program Finder. ^[13]
- City of Chicago Office of Reentry – Jobs & Workforce Training (Fair Chance Hiring employer). ^[14]

Featured Organizations & How to Apply

Safer Foundation

Services: Job readiness, immediate & long‑term placement (light industrial, janitorial, logistics), transitional employment, construction training (RTP), entrepreneurship supports. ^[]

Apply: Register as a client via Safer’s site or call (312) 922‑2200; South Side Job Placement: (872) 298‑1617; address: 571 W Jackson Blvd, Chicago, IL 60661. ^[3][4]

Chicago Cook Workforce Partnership & American Job Centers (AJCs)

Services: Career coaching, ConstructionWorks training, sector pathways (Good Jobs Chicagoland), and the Road Home reentry navigation program with paid work experiences. ^[2][16]

Apply: Use Find a Center to request intake (phone: (708) 580‑8686). ^[1]

City of Chicago DFSS – Transitional Jobs

Services: Paid transitional employment + wraparound services; operator locations (Cara, NLEN, Haymarket, Westside Health Authority, Salvation Army Harbor Light, etc.) and phone numbers listed on the City page. ^[5]

Apply: Call your nearest operator from the City page and enroll for paid work experience with coaching. ^[5]

CTA Second Chance Program

Services: One of the largest reentry employment programs nationwide; paid temporary full‑time assignments, training, mentoring, and pathways to permanent roles; apply via partner referral. ^[6]

Partner Examples & Contacts: Cara Program (312‑798‑3300), St. Leonard’s Ministries/Michael Barlow Center (312‑226‑6270), St. Sabina ERC (773‑783‑3760), Westside Health Authority (773‑786‑0226). ^[6]