How to Tell If Your Child Is Going to Get an Actual Education in a Chicago Private or Parochial School

Lessons from the parental trenches in admissions questions and school tours

So, you're considering sending your kid to a private or parochial school in Chicago.

Congratulations on dodging Chicago Public Schools (CPS) — educational roulette at its finest, where your zip code/tier determines whether you're signing your kid up for scholastic Squid Game or just worshipping at the altar of an intersectional dumpster fire (sacrificing your kid to the equity gods optional).

But here's your new problem: Trading one experiment for another.

Unless you ask the hard questions up front, you won’t know whether your child will become a guinea pig in some private or parochial school's latest educational crusade.

Trust me, you're not alone in this mess.

More parents are asking the same question: "Will my kid learn actual stuff or just master the art of performative empathy while eventually cramming for selective enrollment or standardized tests with an outside tutor?"

If the school you're considering is affiliated with NAIS, ISACS, or Prizmah, there's at least some chance it's been exposed to (or infiltrated by) the progressive mind virus — whether at the board, administrative, or teaching levels (or all three).

Here's the unvarnished truth from someone in the trenches (from a dad who's gone through it firsthand and whose better half is on a board at a private school and has seen it all).

‍The reading wars‍

First up, and arguably the most critical, are the reading wars. This topic shouldn't be political, but welcome to 2025.

Expecting your child to learn to read in school shouldn't be revolutionary, but don't take it for granted in K-6.

I've watched two of my kids struggle through this nightmare at a fancy North Side Chicago private school. And just this weekend, I caught up with another family (an old friend from childhood) dealing with the same circus at a different North Side institution.

It's a problem. And no number of Instagram-worthy reading nooks will fix it. Nobody cares about cute pillows if your kid can't read the books on them.

If the school says phonics is "too rigid" or claims it's outdated, they're either uninformed or choosing ideology over proven science. Phonics isn't rigid— it's effective.

Here's what to ask when touring schools:

‍Ask: "What's your reading program?"‍

Good answer: Wilson or Orton-Gillingham (or something similar that is battle-proven).

Red flag: "Balanced literacy," “whole Language”, “site reading,” or anything other than phonics (translation: your kid may need expensive tutoring).

‍Ask: "How do you track reading progress?"‍

Good answer: NWEA MAP, IAR and DIBELS (earlier in the educational journey)

Red flag: "We assess holistically" (translation: your guess is as good as ours).

‍Ask: "What happens to struggling readers?"‍

Good answer: "We flag them immediately, notify you before the next report card, and, with your permission, start intervention immediately."

Red flag: "Push-in services" (education-speak for band-aids) or "we can recommend out-of-classroom specialists/tutors" (translation: you'll be paying twice and likely too late to keep them at grade level in the formative early years).

Other reading red flags include schools that shy away from ability grouping in the spirit of "equity" or anything that sounds like a holdover from the Biden administration — such as "culturally responsive texts" at the expense of foundational skills.

Representation in books is fine if you care about that sort of thing, but it can't replace structured lessons in decoding, fluency, and comprehension. Schools focusing more on book themes than reading mechanics set children up for failure.

Reading is the foundation from K-6 (especially in the early years), but other areas can reveal a school's true colors and whether your educational investment is worth it.

‍Gender/sex‍

Direct questions get direct answers. For example: "How many genders do your biology and health classes teach?"

Sports and sex also matter — especially for girls.

You shouldn't have to worry about your daughter getting a broken nose (or worse) in volleyball or lacrosse from a biological male with a killer spike (or check) and a Y chromosome.

So ask:

"Are biological boys allowed to compete in girls' sports after they’ve gone through puberty?"

"Does your bathroom policy allow individuals with penises (or male genitalia, if you’re more proper than me) to use the girls' restroom?"

This is about ensuring basic dignity for all students. "Everyone shares everything" is not a policy — it's a recipe for disaster.

If a child is confused, by all means, let them use a single-room bathroom. But if the school's response is anything other than that, it’s a warning flag. 

‍Race, merit, and viewpoint diversity

If you’re touring a school for nursery, pre-K or K-6, ask if they have Amazeworks intersectional dolls, a valid first sign that anti-racism (read: racism) has indoctrinated at least someone at the place (note: At one private school in Chicago, a former parent, who yanked her kid out, but not before asking whether these dolls were appropriate, was allegedly labeled racist by an administrator for asking this question — who denied ever making the accusation when asked after the fact about the incident by Chicago Contrarian).

Beyond affinity group dolls, start by asking:

"Does the school treat all students equally, or are some treated differently based on their race, gender, or other identity factors?"

Look for signs of equity mission creep — like assigning privileges, punishments, or scholarships based on demographic checkboxes. Fairness isn't a buzzword; it's a foundation.

Other key questions:

"Do you include topics of race/racism in math and science?"

"Does the school divide students into affinity groups by race?"

This may sound like I’m crazy suggesting this, but I’m not. Some NAIS-affiliated schools teach that math and science are racist, even as part of physics class! 

So be sure the school teaches math as math — not as a tool of colonial oppression (spoiler: It isn't).

And affinity groups? That’s segregation under a new name. 

Hint: If it feels wrong or anyone is being treated differently (or segregated) based on any immutable basis, it probably is.

Also, ask how the school handles viewpoint diversity:

"Can students question the party line without being labeled problematic or harmful?"

"What's the school's commitment to intellectual diversity?"

Good schools have real-world proof: debates, guest speakers, and robust discussion — not slogans.

Finally, ask if disciplinary rules are applied evenly. If one kid gets detention for claiming there are two genders in health class or chewing gum in the hallway, but another walks free after disrupting class because of "trauma," you've got a problem.

‍Anti-Semitism

Being Jewish at some schools these days is like wearing a MAGA or IDF hat to a CTU rally—as Jordan Peterson might say, “good luck with that.” 

So ask, regardless of whether you’re Jewish, as it’s a great “tell” about the school, something like, “what's your school's policy on anti-Semitism?"

A good school has zero tolerance and clear examples of enforcement.

Drill down: "Does the school allow BDS activism?"

Supporting free speech is fine, but letting kids turn the cafeteria into a Hamas love-in that scares Jewish students away is not.

Finally, ask: “Does the school teach the Holocaust and Jewish history?"

If they gloss over 6 million deaths, they're not doing history — they're doing revisionism CTU style.

‍Bottom Line

You're not just buying education — you're buying twelve years of your kid's brain space. 

A good school will welcome these questions like a confident chef is ready for the Michelin reviewers. 

Bring ‘em on. 

If they start squirming, take your tuition elsewhere.

Remember: Your kid needs to learn about the world, not how to fix it, and must start by mastering reading and algebra. Let the Blue Sky activists (who fled X because they were triggered) mold the next Greta on their own time — you focus on finding a school that teaches your kid to read and, then, reason, not what to think.

Said another way: make sure your kid does the math, not “the work” — code for cultural Marxism in the classroom.

And if anyone gives you grief for asking these questions, it’s not the right place. And remind them that your tuition check buys you the right to be that parent — the one who asks uncomfortable questions now so their kid won't need uncomfortable therapy sessions later.

If more of us ask questions like this, Chicago’s private and parochial schools will return to focusing on academics, athletics, and character rather than preparing kids to collect unemployment in the fast-emerging AI/agent world that won’t care about their pronouns.

Now, please excuse me on this Sunday night. 

I’m about to pour my second Oban — Bryan Johnson be darned — and finish the second season of Squid Game (the actual show, not what happens inside CPS). 

‍

J.D. Busch is a technology entrepreneur, investor and essayist.