Would never have happened after 2000
One thing I noticed in our current culture is how convenient it is to have internet and cell phones. Due to not having either in 1990 (I'll explain the cell phone thing below), and the trees falling in the wind storm and messing up the phone lines (that's Chicago weather for you), and everyone on the street being gone during the holidays, Kevin was completely cut off from communicating with his family, and vice versa.
If this family had left Kevin behind today, they would have easily been able to talk to him on cell phones and Skype, regardless of what the trees did to the power lines today. It wouldn't have taken very long to fix those, and with WiFi, it would have taken a LOT more to cut Kevin's family off from communicating with him in this day and age.
Note: while cell phones did exist in 1990, and were invented in the late 70s/early 80s, nobody used them, save for very, very rich people, such as business executives and billionaires, and even then, they had limited range, were the size of bricks, and only worked in certain areas. Heck, cell phones didn't become cheap, easy to use, and have better reception until 2001/2002. So even if Kevin's family had owned a "brick phone," he was still screwed in Christmas of 1990.