I loved Chicago last time I was here, so I'm planning ahead.

I've been told Chicago is known for it's super awful winters, so when does the Chicago cold/winter weather kick in? As much as I'd love to be snowed in I do have school to get back to.

Thank you! :3

Having lived in Chicago for my entire life, Chicago's weather can be rather unpredictable between seasons.  The coldest months are usually January-February, but December can get pretty cold too.  As for snow, that's even more unpredictable.  Although in the past, some of the biggest snowstorm have occurred in January and February.

Some winter have been pretty mild too, in regards to temps and snow, so you just never know.  I think the best thing to do is to keep checking the extend forecast as winter approaches.

The weather has been super bipolar... So it's hard to exactly point out the polar vortex conditions..  

Spring & fall are beautiful in Chicago the weather is purf, not too hot & not too cold  

Hope this helps  

Like Gemma said, the last few winters here have been very mild in comparison to the norm. Snow has been starting in late December/January over the last few months, and January isn't a time you'd want to come here anyway. Really super cold days normally don't show consistently until mid January.  

Assuming we have repeats of the last few winters, it'll be in the high 20's/low 30s well into December, with some colder days overall. You'll need a winter jacket for sure, and perhaps an umbrella (it rains a lot in the latter part of November/beginning of December) but you won't be knee-deep in snow for a while.  

Of course, weather can be unpredictable, but it has been milder over the last few years.  

Good luck!