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Sofia's station is right at downtown, and I assume Chicago's downtown is warmer than Midway, so Midway is a much more appropriate station to use than O'Hare.
Both have pretty bad winters, but Chicago's is worse. It's close but if I had to choose, I'd choose Chicago for warmer and more humid summers and more thunderstorms. There isn't much of a sunshine difference considering the inflated US hours. Chicago is much more windy in winter, and that may make it closer than what the weather boxes suggest.
If I compare Chicago O'Hare to Sofia, Sofia seems slightly better.
Sofia seems a bit less continental, closer to Boston's climate, but with cooler summer and milder winter nights. While I prefer Chicago's additional precipitation, Sofia seems more comfortable in summer due to the lower humidity. I also prefer Sofia's milder winter, although Chicago has more sunshine.
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