Chicago ERA matched participants with a career and income advisor (CIA) who counseled them about how to advance in their current jobs and apply for higher-paying jobs. Participants could receive other education and training services and financial incentives for maintaining contact with their case manager to verify their work hours. A30-hour work requirement was part of their TANF participation, and failure to work at this level could result in a sanction of their TANF benefits. The program served participants for up to  two years, even if they left TANF.

Traditional Case Management participants worked with one case manager to improve educational and vocational skills and with a separate income maintenance case manager to determine their welfare eligibility and payment issuance. Participants who did not have a high school diploma or general education diploma were assigned to basic education classes; participants with basic education credentials were assigned to vocational training, postsecondary education, or work experience. Case managers provided job search assistance after they determined that participants were employable.

STEP participants received home visits from community liaisons to identify and mitigate any barriers that might prevent participants from traveling to the program offices. In the program offices, participants were assigned a case coordinator, who conducted assessments to determine barriers to employment. Case coordinators worked with no more than 20 participants at a time. The case coordinator and specialized vocational rehabilitation staff developed a plan to address the barriers, and participants began activities tailored to overcoming their barriers.