It rampages through the city like a plague every December through March.
Leave home in the dark, get home in the dark, it's overcast when you do go outside.
Snow comes and goes, it gently falls constantly due to "lake effect", and you'll have a few 10" snowstorms from November through February. Plus a couple random 40-60 degree days where it all melts off.
There is a ski hill (Cannonsburg) half an hour away, but it's only a hill - not a mountain. People ice fish, snowmobile, play hockey, and generally enjoy the winter - but you have to get out and use the right lights, or else you'll join most of the rest of the city in some mild depression.
When my son graduates high school, and our network of great schools, family, and friends becomes less of a tie, I'm running.
Now the summer time is a completely different story...
Here is Grand Rapids [2].
[1] https://www.usclimatedata.com/
[2] https://www.usclimatedata.com/climate/grand-rapids/michigan/...
I was born here so I am fine but I have met SE Asian, Indian and Japanese people here who were kind of miserable. But you get used to it after a while.
Lake Michigan has a large impact on weather patterns. Grand Rapids on the east and Chicago on the west do not have the same weather in the winter. Lake-effect snow is rare in Chicago, and the colder it gets the higher the likelihood of sunshine. Many days it will feel as though sunglasses are a safety item.