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I think there is an unwritten code in Chicago to start fretting over school options somewhere between the time the stick turns blue and the time you square away your co-pay on the way out of the doctors office. Ok, maybe it's not that fast, but I am not that far off. I remember taking my son to the park at around 10 months and getting roped in to a school conversation. What?! My son just spit up breast milk and I am supposed to have his future mapped out? When I left the park that day, I couldn't help but feel we were "already behind the 8 Ball" regarding school choice.
At two and a half we found a nice fit at a Montessori school for our son. We felt Montessori fit his personality and fit our schedules as well. Before that, we had managed to get by without daycare so this was our first "split" from our son. At over a thousand dollars per month, the price tag put us in the poorhouse for a bit, but in the end we feel it set Leo up on the right path.
The fun really started when it came time to start the search for kindergarten. Every dinner-party, play-date, stroll-in-the-park, line-at-the-DMV conversation turned to school updates. Who applied where, who visited here, who had an "in" somewhere, who put the bop in the bop shoo bop, etc. I remember going to an open house at an up-and-coming public school and having to stand in line 20-something deep to shake the principal's hand. Last time I waited in a line like that it had a roller coaster at the end of it.
In the end we chose a private Catholic school for our son. We had been accepted to some nice public schools on the north side but at the end of the day, we had to make the decision based on what school was the best fit for him.