Best time to go to Chicago, December or February?!

December better than February. Winter can be bitterly cold in Chicago. December has a chance of being mild more than February.

I went in December and remember there being a lot of Christmas lights but that was a very long time ago. It was still flipping cold for a Brit like me though.
I was once in Ann Arbor Michigan looking out my hotel one morning at snow, snow and more snow and the weather report says "Likely to be below zero". I even say out loud back at the tv "No shit Sherlock" until I remembered that he meant below zero Fahrenheit. 🤦🏼‍♂

I have been in December - they really decorate for Christmas and I enjoyed it a lot. Don’t know about Feb. - never been.

Thanks for sharing your full itinerary.

Definitely December... I did a trip there in late January, and it was brutal cold and snow covered. I stayed at the Drake that time, and the winds off the lake near froze me even wearing my heaviest coat.

December is best. Do the Kris Kringle market downtown. Hopefully it will snow while you’re there so you can fully immerse yourself in the experience.

Great Ideas, Everyone! I'll start planning at the end of this month!

I would go in December and do your Christmas Shopping there.

December for holidays. After that the winters are dreadful

Definitely December....February gets pretty raw!!!

February will be the coldest and snowiest month.

I went in May so I really have nothing to compare to

Any other month than those !!

Go for the holidays.

No, hahaha

Dec for sure!

June

April, unless you want to freeze