How Ex-felons Can Rebuild Their Life in Chicago?

5 days ago5 min read

Life after incarceration can feel overwhelming. You will feel burdened by your experiences and face many challenges as you work to rebuild your life. However, Chicago offers several tools and programs to help you move forward.

In this blog post, you’ll learn about legal reentry, housing solutions, job opportunities, financial support, and civic participation to help reclaim your future. Each section gives you practical steps to overcome the obstacles in your path.

Overcoming Housing Barriers

Finding a safe place to live is essential. A criminal record can make renting or buying a home difficult. Many ex-felons face rejection from landlords and lenders. But hope isn’t lost. Illinois’ “Ban the Box” law prohibits landlords from asking about criminal history on initial applications. Use this to your advantage.

You can also access local support programs that assist with housing applications and provide guidance on securing a lease. Explore options like Section 8 housing or nonprofit organizations that help ex-offenders find affordable housing. Government programs like Temporary Assistance for Needy Families (TANF) offer financial assistance and support.

Accessing Employment Opportunities and Skill Development

Finding a job is a common challenge. You may face stigma when you apply for work. Chicago offers job fairs and reentry programs focusing on hiring people with criminal records. For example, United Legion One Nation (U-LON), a nonprofit, hosted its first-ever Project Hired Job Fair in 2023.

According to ABC7 Chicago, Peter Keller, a former gang affiliate and drug dealer turned activist, established this non-profit. He aims to help those with criminal backgrounds secure stable employment. At the job fair, employers interviewed candidates on the spot. Over 20+ companies hired dozens of ex-felons. One attendee, Maurice Brown, landed work after months of rejection, proving persistence pays off.

The Chicago Transit Authority (CTA) has supported this effort since 2011 with its Second Chance Program, one of the nation’s largest reentry initiatives. Over 3,000 Chicagoans have gained skills through paid apprenticeships in roles like bus mechanics or custodians. Connect with partner agencies like the Safer Foundation or St. Leonard’s Ministries to apply. These groups refer candidates to the program and provide job-readiness training.

Participants earn $16.67/hour, work up to 40 hours weekly, and receive free CTA transit passes during their 12-month term. After completing the program, many secure permanent roles at CTA—like 600+ graduates—or transition to private-sector jobs. Success hinges on consistent attendance and adherence to CTA policies. For details, call the Second Chance Hotline at 1-312-681-2293.

Reconnecting With Family and Community

Rebuilding your life means reconnecting with loved ones and becoming an active community member. Strong family ties and supportive friendships can significantly accelerate your rehabilitation process. Attending family gatherings, joining community events, or participating in support groups can provide emotional support, accountability, and a sense of belonging.

Simple acts—like attending a niece’s birthday party or joining a neighborhood clean-up—rebuild trust and purpose. But getting there isn’t always easy. Transportation barriers can isolate you from these critical moments. For example, group outings to therapy sessions or job fairs often require smooth rides. Reliable transportation, like Sprinter van rental in Chicago, lets you travel safely with family or peers to these events.

Eminent Limo reveals these services cost between $100 and $135 per hour. Also, vehicle choice will reflect the price. While it is a bit pricey, you can share it with other adults to offset the cost. Just imagine taking your kids to a museum or carpooling to a reentry workshop. These small steps strengthen relationships and accountability networks. You create a support system that accelerates your reintegration by prioritizing these connections.

Financial Empowerment and Business Opportunities

Many ex-felons struggle with financial instability, thinking their past limits their ability to secure loans or start a business. Yet, grants and funding options designed for such situations can help you.

NerdWallet discloses that you can access a variety of nonprofit and corporate grants designed for formerly incarcerated individuals. Programs like the LEAP Virtual Entrepreneurial Academy offer training to help you develop essential business skills. It can also provide a $1,000 microloan. The Rise Up, Get Started Grant Program includes a year-long mentorship, coaching, community support, and a small grant to jumpstart your venture.

The Georgetown Pivot Program in Washington, D.C., offers a full-time fellowship with a weekly stipend and prize money through a business pitch competition. You can also explore opportunities such as the Transform Business Grant, which gives a $1,000 microgrant alongside a customized year-long business development plan.

In addition, women entrepreneurs may consider the Amber Grant, which awards monthly and annual funding to help boost their business dreams. Furthermore, you may benefit from the NASE Growth Grant, which offers up to $4,000 in funding. Likewise, Bizee’s Fresh Start Business Grant covers incorporation costs and provides $2,500.

Government grants through Grants.gov and local Economic Development Offices also offer support. Finally, Help For Felons, Inmates to Entrepreneurs, Defy Ventures, Project Remade, Entre Capital, and Drive Change provide training and guidance to help you succeed.

Civic Participation and Overcoming Social Stigma

Being an active member of society is crucial. You have the right to vote and contribute to community betterment. Understanding your rights is the first step toward reclaiming your voice.

In Illinois, you can vote the day you leave prison—even on parole. However, you can’t vote if you’ve been sentenced or are serving jail time. Your voting rights are reinstated when administrators remove your data from the felony conviction registry. But you still have to re-enroll to vote once you complete your prison sentence.

Voting impacts policies like job programs and housing laws. Voting and engaging in local events helps you change negative perceptions about ex-felons. Your involvement strengthens the community and builds trust. For instance, after much discussion, Illinois will allow resentencing for those convicted under age 21.

Nelson Morris, a 17-year-old, was apprehended for double murder. He was awarded life imprisonment with no parole. According to the Chicago Tribune, after serving his sentence for nearly 3 decades, he was released in August 2020. Illinois has scrapped life sentences without parole for most offenders under 21.

This law means the state became the 26th state to outlaw such convictions from being implemented on those under 18. Morris is now a development manager at Restore Justice, a criminal justice reform organization.