Youth Mentor​/Respite Support; Part-Time Kaleidoscope – Chicago, IL

$27/hour | Up to 20 hrs/week | Paid Travel + Mileage | Remote

This is a field-based position. You must live in Illinois and be able to travel throughout all of Cook County to visit youth in their homes, schools, and communities.

Make a real impact with youth across Chicago. Kaleidoscope is a child and family services agency dedicated to helping young people heal, grow, and thrive. We deliver individualized community-based support grounded in compassion, respect, and genuine partnership.

We are hiring Part-Time Youth Mentors to support our Enhanced Clinical Community Support (ECCS) Program. This role is ideal for someone who enjoys working directly with youth, values strong supervision, and wants to be part of a highly supportive and mission-driven team.

For a limited time, we are offering a $500 signing bonus!

• Travel across Cook County to visit youth in homes, schools, and community settings.
• Provide mentoring, support, and respite for youth and caregivers.
• Engage youth in positive community activities.
• Model coping, communication, and social skills.
• Transport youth as needed (paid travel time + mileage).
• Follow through on scheduled visits and commitments to families.
• Join team check-ins, supervision, and paid training provided in trauma-informed care, developmental delays, and therapeutic mentoring techniques.
• Complete clear, and timely documentation within 48 hours.

Schedule includes afternoons, evenings, and weekends.

• High school diploma or equivalent.
• 1+ year experience working with youth.
• Must live in Illinois and be willing to travel across Cook County for visits.
• Age 21+ with a valid driver’s license + insured vehicle.
• Strong communication, reliability, and patience.
• Comfortable using email and video meetings.

trauma-informed experience or bilingual.

Kaleidoscope is a supportive, mission-driven team. Our work is grounded in core principles that guide how we show up for youth, families, and each other:

• Lead with empathy and non-judgment.
• Practice self-awareness.
• Name power imbalances and structural limitations.
• Center youth, caregiver, and team voice and choice.
• Demonstrate flexibility and resourcefulness.
• Balance healthy boundaries with authentic relationships.
• Connect with our purpose.
• Prioritize self-care.
• Commit to critical thinking and curiosity.
• Celebrate strengths and successes.

• Paid travel time + mileage reimbursement.
• Paid training and ongoing development.
• Supportive team + strong supervision.
• Flexible, hands-on community work.
• Direct, meaningful impact on youth and families.

Our contract requires background checks that include: criminal, education, and motor vehicle.