10 Ways to Prepare Your Freshman for High School in Chicago

By Debra Flanagan, Macaroni KID Chicago Northside August 9, 2023

It's hard to believe summer is almost over. If you have a rising high school freshman at home, you might be getting a little anxious right about now. Having gone through this process just last year, we have a few recommendations to prepare you and your child for high school.

  1. Start practicing the CTA, (if not for commuting to school, for their soon-to-be-growing social life.)
    • Note, schools will issue Ventra cards to students, but if you have one already, they will be able to connect it to their student ID to obtain student fares.
    • First day of school on CTA is free.
    • High School students pay a reduced fare on CTA during student fare hours only. ($0.75 M-F 5:30am-8:30pm)
    • Register your card at or download the app, for online account management features.
    • Highly recommend setting their cards up to automatically reload when the value gets low, so they are never left stranded!
    • For more information go to
  2. Set them up with a debit card.
    • Many banks offer student debit cards.
    • Those partnered with Greenlight Debit, include automated ways for students to earn money from the completion of designated chores or weekly allowances.
    • It gives the parents a way to see what the kids are spending their money on. (My daughter spent an unreasonable amount her first weeks of high school at school vending machines!)
    • Since you have the power of adding money to their account at any time, it is an easy way to get money to them in case of an emergency too.
  3. For holidays/gifts, ask family to give your student gift cards to the various eateries around their high school, especially if they have off-campus lunch privileges.
  4. Add the Uber, Lyft, or Curb apps to their phones linked to your payment method.
    • This will give you a little peace of mind that they always have a way to get home safely.
  5. Consider a personal alarm, such as Birdie, but there are tons of brands out there, particularly if they will be using public transit.
  6. High School students typically wait til school starts to find out what school supplies they need. 
    • However, get a sturdy backpack. 
    • Depending on their locker locations, they may be carrying quite heavy loads around all day, not to mention potential sporting equipment, etc.
    • Note, some of the expensive calculators required for algebra may be rented for the year.
    • They may have special requirements for swim class, i.e. one piece bathing suit, swim cap, etc.
  7. Purchase some locker accessories.
    • Depending on whether they are sharing a locker or not, there are some great items on Amazon to help organize their lockers, such as: hanging shelves, magnetic mirrors, magnetic dry erase boards, Command hooks for coats, and even magnetic wallpaper.
  8. Anticipate school fees at the onset of the year that can run in the hundreds of dollars depending on the school. 
    • These fees cover things like gym uniforms, combination locks, student ids, yearbooks, lab fees, etc.
  9. Make sure their space at home is clean, organized, and ready for studying on day one.
  10. If not already, you might want to consider a parental control app for their phones, like Bark or Life360.
    • We observed a huge change in kids over the summer between 8th and 9th grades. Freshmen are drinking, freshmen are vaping, freshmen are having sex. It is alarming and it is no time to take your foot off the parenting gas. They need you now more than ever.