You can grow Phalaenopsis in pots outside in Chicagoland. I'm not in Chicago but I have a similar weather condition here in Fort Wayne. When overnight temperatures remain above 55*F and there is no possibility of frost, I put all of my plants outside in my screen porch that is on the north east side of my house--around mid-May. They stay there until September's end.
If you are concerned with root rot, you should water your plants in the morning, shake off any water that is accumulating in the crown. Being outside, there is a lot of air movement that would dry off the rest of the water. In fact, I water my plants more often outside in the summertime.
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