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I'm a special education teacher >with a pretty far commute to work.... Should I tell my >administration that I'm looking?

No one can give you perfect advice here. You really need recommendation letters to apply, but that entails telling your boss you're looking. Bad situation. You know your boss better than anyone on this site. If he/she is the kind who would take it badly that you're looking for another job, then you should probably keep it quiet. If they're sensible, and might understand the long commute is a reason to look, then maybe take a shot. It's impossible to know for sure, but if he/she is known for holding petty grudges, you might not want to let them know.

Now, I would at least wait on telling them until the dead-line has passed in your district for non-rehires. Unless it's longer by union contract, it is 45 calendar days before the end of the school year by Illinois School Code. This is likely coming up soon if it hasn't already passed.

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