The sensor was moved many years ago, and it's probably in one of the better possible areas it can be at this time. The NW/W/SW side of the airport has the most bits and pieces of open land at this time, and even that is going to vanish eventually. After Route 390, I-490 and the new terminal are fully complete several years from now, there really won't be a "good" place for the ASOS. I'm guessing that is when ORD will have a shot to overtake MDW as the consistently warmer location.
It's all relative really. ORD was 76.7 this summer and MDW was 76.4...So MDW still would have tied the record. If you dig into it even further, in 2012 ORD was 76.1 (now 4th warmest summer), but MDW was 77.3...which would have blown away the old 1921 record and new 2020 record for warmest summer.
Re: Jan 2019 cold...ORD was right on par with MDW and PWK for low temps during that time. The coldest readings were in the usual cold spots, outside of the immediate metro.