![]() ![]() ![]() □ Check out our Chicago hotel guide.Ĭhicago’s brief warm temperatures are as muggy as they are brief, so many tourists prefer to visit during cooler times. Of course, there’s often much warmer weather, albeit briefly, during our construction season in late June, July, and August. You see, in Chicago, we only have 2 seasons - “winter” and a brief period we like to call “construction.” In Chicago, you can expect cold weather from September all the way through to June (sometimes even in the summer). What to Wear in Chicago: Cold Weather Outfit Guide.
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