Mentor for a Teen or Young Adult in Chicago, by Video

Blackburn Mentoring offers online mentoring in Chicago: one-on-one mentoring and coaching by video for teens 13 and up, college students and young adults in the city, the North Shore and the suburbs, with sessions in Central time. Mentoring since 2014, it starts with a free 20 minute intro call, and new clients are matched with a mentor within 2 business days.

Our team is in Los Angeles, so Chicago clients work with us by video. Sessions run weekly or several times a week, with text and phone check-ins between them, so the plan keeps moving even when the weather does not.

Planning for the long winter

Chicagoans know the pattern. Fall is busy and energetic, then November arrives, the wind comes off the lake and daylight disappears early. By January, getting to the L or the Metra platform feels like an accomplishment. Motivation dips for students and adults alike, and good habits from September fade.

We plan for winter before it starts. A mentor helps a client set up:

A fixed wake-up time and morning routine that does not depend on sunlight
Indoor exercise that is scheduled, not hoped for
Weekly goals cut small enough to finish during the darkest stretch
Standing plans with friends or family, so weekends do not disappear

If winter brings a low mood that does not lift, a licensed professional is the right step, and a mentor can help you find and keep that appointment. In a crisis, call or text 988.

Session times from Chicago

Chicago is on Central time, only two hours ahead of our Pacific-based mentors, so the whole 4 to 8 pm window lands in a mentor’s afternoon.

After school: 4:00 pm Central is 2:00 pm Pacific, and 5:00 pm Central is 3:00 pm Pacific, once a student is home from practice.
After work: 7:00 pm Central is 5:00 pm Pacific; 8:00 pm Central is 6:00 pm Pacific, which helps after a long Metra ride from the Loop.
Early morning: a 7:00 am Central session before school or the commute can be set up with a mentor who starts early.
Weekends: many clients add a short Sunday session to plan the week before the Monday commute.

Chicago by the numbers

These figures cover the Chicago-Naperville-Elgin metro, which runs from the city through the collar counties into northwest Indiana and southern Wisconsin. Full profile on Census Reporter.

35.1 percent of Illinois adults ages 18 to 34 live with their parents, above the national 32.9 percent (FinanceBuzz analysis of 2024 Census data, state level). Plenty of Chicago-area graduates move back to the suburbs, and the real question is when the jump to a city apartment makes sense.
A 30.9 minute average commute, among the longest in the Midwest (U.S. Census Bureau, American Community Survey 2024, via Census Reporter). After an hour or more on the Kennedy or the Metra, most students and young professionals would rather meet from home.
A median owner-occupied home value of $339,700 (U.S. Census Bureau, American Community Survey 2024, via Census Reporter). That is far below the coasts, so independence is within reach for a young adult with steady work and a plan.
43.1 percent of metro adults 25 and older hold a bachelor’s degree or higher (U.S. Census Bureau, American Community Survey 2024, via Census Reporter), alongside a deep tradition of union apprenticeships. Families here weigh both paths, and a mentor helps a teen compare them honestly.
An 11.1 percent poverty rate across the metro (U.S. Census Bureau, American Community Survey 2024, via Census Reporter). Circumstances vary widely from one neighborhood or suburb to the next, and so do the goals families bring us.

The Chicago year, and what families ask

Chicago-area districts generally start in mid to late August, earlier than much of the East Coast, and winter break runs from late December into early January. Long, cold winters with lake-effect wind are the defining feature of the calendar, followed by a short, packed summer of lakefront beaches, street festivals and construction season. College students come home at Thanksgiving and winter break, which is when many Chicago parents first notice that a semester has gone sideways.

The regional economy is very large and diversified: finance and trading, professional services, health care, manufacturing, and a national rail, air and freight hub that employs many young people straight out of high school. The questions we hear most from Chicago families: how do we keep a high schooler on track with college applications in a competitive suburb, how do we help a young adult home from college with a job search and independence, can sessions fit around long commutes and after-school activities, and can a mentor help a student struggling away from home?

North Shore and suburban high school students

Families in Evanston, Wilmette, Winnetka, Glencoe, Highland Park and Lake Forest, and across the western suburbs, often have students in demanding public and independent schools. Many juggle a full course load with sports, music and summer programs. High school mentoring here focuses on the skills grades depend on: planning, follow-through, sleep and confidence. A parent or guardian can join the intro call, agree the goals and receive regular progress updates. Our mentors are not tutors or admissions counselors.

College students and young professionals

Students from Chicago often head to large state campuses across Illinois and neighboring states, where lecture halls are big and nobody notices a missed class. Others stay in the city and commute. College mentoring helps with a weekly schedule around class, work and commuting, office hours before grades slip, and internships back home in the summer. Graduates who settle in Lincoln Park, Lakeview or the West Loop use young adult mentoring for budgeting, routines and decisions about the next step.

Situations that come up often in the Chicago area

A young adult starting a building trades apprenticeship who has to be on a job site before sunrise.
A student commuting by Metra or the L to a campus in the city while working part time, with no time to linger after class.
A family relocating from a city neighborhood to a suburb, with a teen leaving every friend behind.

Common questions

Is video mentoring practical for Chicago families with long commutes?

It is one of the main reasons families here choose it. Nobody has to drive or ride anywhere, so a session still happens on a day with a 90 minute commute or a snowstorm, and a standing weekly time gives structure to the darkest months.

Illinois has a high share of 18 to 34 year olds living with parents. Can a mentor help a young adult move toward independence?

Yes. A mentor helps a young adult living at home set a job or school plan, a savings goal and a target date for a first apartment, then checks in weekly. With the young adult’s permission, parents get updates so the conversation at home stays practical.

What times work for Chicago clients in Central time?

Sessions are scheduled in Central time, two hours ahead of our team. A 4:00 pm after-school session is 2:00 pm Pacific, and a 7:00 pm session after work is 5:00 pm Pacific. Early-morning and Sunday sessions are available too.

Can a mentor support a Chicago student who goes away to college out of state?

Yes. The mentor works with the student by video wherever they study, updates the session time if they move to another time zone, and keeps working with them when they come home for breaks or a summer internship in the city.

Does a mentor meet in person in Chicago?

No. We work with Illinois clients by video, with text and phone check-ins between sessions. In-person sessions are available only in Los Angeles.

Is there one-on-one mentoring for teens and young adults in Chicago?

Yes. Blackburn Mentoring works with teens 13 and up, college students and young adults across Chicago and the suburbs by video, scheduled in Central time. It starts with a free 20 minute intro call, and new clients are matched with a mentor within 2 business days.

Get started

Looking for a mentor in Chicago? Call (888) 305-5422, email contact@blackburnmentoring.com or start with a short assessment. A member of our team reviews every assessment personally and sets up a free intro call.

Last updated November 2, 2026.

Book a free intro call Text us

Free, by video, 20 minutes, with a member of our team. Weekdays 9 to 5 Pacific.