Street Outreach and Aftercare Case Manager

Covenant House Illinois • Chicago, IL

2h • $47,000 - $58,000 • Hybrid

About The Position

The Outreach Case Manager plays a critical role in connecting youth experiencing homelessness with housing, resources, and long-term support. This position provides street-based outreach and intensive case management for youth who are unsheltered or in temporary housing, helping them overcome barriers to stability and independence.

This role requires frequent travel throughout Chicago to engage youth where they are — including on the streets, in shelters, hospitals, and other community settings. The Outreach Case Manager works collaboratively with internal teams and community partners to deliver compassionate, goal-oriented, trauma-informed services.

Requirements

• Bachelor’s degree in Social Work, Human Services, or a related field required
• 2–3 years of experience working with at-risk or unhoused youth
• Strong understanding of homelessness, housing instability, and youth development
• Experience working within Harm Reduction, Housing First, Trauma-Informed Care, and Motivational Interviewing frameworks
• Excellent organizational, communication, and time-management skills
• Ability to work independently in a fast-paced, dynamic environment
• Effective crisis intervention and de-escalation skills
• Comfort working with highly vulnerable populations in non-traditional settings
• Ability to accurately document services and manage data systems (HMIS, ETO, or similar)
• Commitment to ongoing learning and professional development
• Ability to manage emotional demands of the role using healthy self-care practices
• Valid Illinois Driver’s License with acceptable driving record
• Ability to drive agency or personal vehicles as needed

Nice To Haves

• Master’s degree preferred
• Experience providing street-based or community outreach services strongly preferred

Responsibilities

• Conduct street-based outreach to engage youth experiencing unsheltered and unstable housing
• Build trust and rapport with youth through consistent, respectful, and trauma-informed engagement
• Provide housing navigation support, including assistance with applications, documentation, and referrals
• Engage youth in diverse environments such as streets, shelters, hospitals, and community locations
• Participate in citywide homeless outreach systems and coordinated outreach efforts
• Respond to youth inquiries via social media and email regarding shelter and services
• Provide ongoing case management and aftercare support for youth transitioning into housing
• Support youth for up to six months post-housing with biweekly check-ins
• Link youth to healthcare, mental health, education, employment, and workforce services
• Assist youth in obtaining identification and enrolling in mainstream benefits
• Attend appointments with youth as needed to support engagement and follow-through
• Coordinate referrals with community-based organizations and service providers
• Develop and maintain strong relationships with community partners, outreach teams, and stakeholders
• Advocate for the needs of youth within community systems and service networks
• Maintain accurate, timely, and organized case records
• Enter data into required systems (e.g., HMIS, ETO)
• Participate in case conferencing, team meetings, and program evaluation
• Conduct follow-ups and wellness checks on outreach and aftercare youth
• Participate in staff meetings, trainings, supervision, and professional development activities
• Support a team-based, respectful, and mission-aligned work environment
• Participate in weekend and holiday rotations to support 24/7 clinical coverage
• Perform other duties as assigned

Benefits

• Safety, shelter, and supportive services
• Wraparound, trauma-informed services
• Interim and transitional housing
• Street outreach
• Workforce and education programs
• Clinical case management
• Life-skills development
• Newly renovated West Side campus
• Recently launched three-year strategic plan
• Expanding impact and deepening commitment to helping young people achieve long-term housing stability and independence
• Youth-affirming work
• Harm reduction grounded services
• Dignity, safety, and respect centered workplace
• Team-based, respectful, and mission-aligned work environment
• Professional development activities
• Diversity, Equity & Inclusion initiatives

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level