Moving from TX with infant. What is it like raising a baby in Chicago?

I (31 F) am thinking of moving from Texas to Chicago with my family— husband (32 M) and son (11 months). I adore Chicago and lived there for a couple of years during college, but have since moved around a bit (Colorado, California, Texas). We live in Texas because of proximity with my family, and have been thinking about moving for a while as it’s less aligned with our personalities but decided to stay when we learned I was pregnant so we could have support from my mom.

My sister-in-law lives in Chicago, but has a very full personal and social schedule as she is child free by choice.

I want to get the good the bad and the ugly of living in Chicago..

What it’s like living with a tiny person in the cold (I myself can tolerate the cold but have fear that it’s a lot for him), if it could be not too difficult to build community again, children activities year round, cost of living , what it’s like raising a child at all stages (infant/toddler/teen), schools, neighborhoods, culture, or anything that you would like a family or friend to know..

I’m probably going to move up there for a couple months to try it out first, and then decide if we want to make it a longer stay with a proper move as we own a home in Texas that we bought when interests were low… so we cannot sell that home .

Thank you!