Hmm, meh, I feel like you can say a lot of pretty similar things about San Francisco and the Bay Area too. Let me defend Chicago with some counterpoints!

- Weather: Sure, SF Bay Area wins here in terms of what you might think of as regularly experienced weather, but it is not without its extremes. Let's recall that most of California, including surrounding SF Bay Area, has been in an extreme drought for the past several years [1], threatening local agriculture and water supply. Also, SF is famous for extremely devastating earthquakes that happen every so often [2] (though, you may not categorize seismic activity as weather, but still a natural occurrence sort of thing).

- Government: SF has its fair share of recent government corruption [3, 4] as well as historical seediness/lawlessness [5], not unlike some of Chicago's history.

- Traffic: Personally, I think the Bay Area has worse traffic than Chicago. The data in this report [6] seems to agree, ranking SF/Oakland as #3 worst in the country and San Jose as #5, whereas Chicago is #8 on the list. And, really, waiting on a few trains to pass for a sports game or special event is not unique to Chicago. Try taking the BART across the bay for a Giants game, Super Bowl 50, Bay to Breakers, Pride Parade, etc. I mean, every city's transportation system hits its limit with big events/gatherings. So what? It's part of living in a city that you learn to accept.

- Wages: Can't debate it. Chicago software engineers, making average of $76k/yr [9], do get paid less than SF, at $110k/yr [10]. But, also consider that income tax in Illinois is a flat 3.75% [11], whereas California's income tax for that bracket is 9.3% [12]. 5.5% more tax in CA is not small. (Federal income tax will also be lower in Chicago with the lower salary, but I haven't looked up those numbers.) And, let's consider cost of living more in general. This handy website [13] says that "A salary of $76,000 in Chicago, Illinois should increase to $178,313 in San Francisco, California", which is mainly due to housing being 428% more expensive in SF than in Chicago. That says a lot! You might interpret that as the $110k/yr average salary in SF actually gets you less quality of living than the $76k/yr in Chicago (according to this website). Or something like that. Don't know, but my housing quality in SF is twice as much for half the space as compared to what I had in Chicago. (What am I doing here?!)

- Crime: According to this (presumably reputable) data [7, 8] Chicago has been steadily improving in terms of crime over the past more than a decade. SF has been kind of steady, and, according to that data, is actually worse per capita than Chicago. I didn't expect that at first. Chicago is a much bigger city and than SF, so that kind of helps to dilute crime among the population, I suppose. Anyway, my anecdotal evidence from friends tell me that it is improving. We must have different kinds of Chicago friends. Or maybe we should trust data instead?

- Schools: SF public schools have a lottery system too [14]. I will grant, though, that CPS does have a lot of ongoing battles with the city and state for funding, like recent closings and strikes. That stuff sucks because it's usually the poorest schools that suffer the most. Ultimately, this is a bigger societal problem than us engineers debating about where the best place for us to live is on a web forum. (Probability of existential crisis increasing...)

Okay. Got that off my chest. I love Chicago. I hope you and others do too still. I may move back soon. Writing this stuff down has, well, made me think twice about wtf I'm doing out here on the West Coast...

1. http://droughtmonitor.unl.edu/Home/StateDroughtMonitor.aspx?...
2. https://en.wikipedia.org/wiki/1989_Loma_Prieta_earthquake
3. http://ww2.kqed.org/news/2016/01/22/3-former-fundraisers-for...
4. http://www.sfgate.com/crime/article/I-am-guilty-final-S-F-co...
5. https://en.wikipedia.org/wiki/Barbary_Coast,_San_Francisco
6. http://247wallst.com/special-report/2015/08/28/10-cities-wit...
7. http://www.city-data.com/crime/crime-Chicago-Illinois.html
8. http://www.city-data.com/crime/crime-San-Francisco-Californi...
9. https://www.glassdoor.com/Salaries/chicago-software-engineer...
10. https://www.glassdoor.com/Salaries/san-francisco-software-en...
11. http://www.bankrate.com/finance/taxes/state-taxes-illinois.a...
12. http://www.bankrate.com/finance/taxes/state-taxes-california...
13. http://www.bestplaces.net/cost-of-living/chicago-il/san-fran...
14. http://www.sfusd.edu/en/enroll-in-sfusd-schools/how-to-apply...