I think Chicago and IL are slept on in general but have a lot of long term positives. IL (thanks to Pritzker and a post-Magidan House) is starting to shore up fiscally, Lake Michigan (for both recreation and water supply) and a decent public transit system make it very appealing.

Chicago is a good choice but a lot of people wouldn't be able to tolerate the winter.

It can be brutal to get through. The bonus on the other side of it is that the summers are amazing with all of the public beaches and summer events going on.

Chicago is a great city.

Cold climate, warm people, actual downtown with actual transit, great food, great diversity, affordable, actual amenities and great intellectual life.

The cold climate isn’t too different from Toronto (and no it’s really not that windy).

Down 22.7% in Work Trips to its metro area compared to SF's 32%. It's possible that it's less dependent on the foot traffic, though.