> Chicago is the best city in the world from June-Sep
I'm a Chicagoan who works for a successful Chicago startup, and I'm planning to leave this year precisely because I strongly disagree with "Chicago is the best city" (at any time of year). There are things that I appreciate about the city (which can be gained from occasional visits rather than residence), but here are some of the things that are driving me out (I'm not sure the extent to which these things have a bearing on its success as a tech hub):
1. There's virtually no nature within a 2 hour drive (you can hardly get past the suburbs in 2 hours after work). There are a few decent state parks (e.g., Starved Rock) that one could do in a day or two, but it's not like Seattle, Denver, or Phoenix where you can be in the mountains in ~40 minutes during rush hour. It seems like Chicago is a great city if you're big into sportsball and clubbing, but for those who want more from life, it leaves a lot to be desired.
2. Chicago has a few charming neighborhoods and the architecture downtown is beautiful, but in general most of the city is kind of ugly (lots of trash blowing around the streets). I particularly hate all of the vomit-yellow brick buildings that plague the north/north-west sides of the city. The more charming neighborhoods are also pretty unaffordable for most Chicagoans.
3. Even with respect to the weather, Chicago is hot and humid from June through August, which makes it pretty unpleasant to be outdoors for most of the day unless you're on the lake (which is invariably crowded). And of course from January through May, Chicago is either cold and bleak or muddy and bleak. If Chicago has a peak time, I would argue that it's September through December.
4. Chicago is deeply politically dysfunctional with respect to fiscal policy, policing, prosecution, etc (and things at the state level aren't much better). I'm happy to pay more in tax to a government that uses that money effectively, but Chicago's taxes are steep and it doesn't seem like that revenue is efficiently used. It's also extremely segregated--when people talk about "Chicago", they're almost always talking about the north side specifically. South and west sides may as well be in different states (if not countries) to most of us north-siders except for the overflow of crime (which admittedly isn't as bad as the news makes it out to be--we're not the worst city in the US for violent crime, we're "merely" the tenth worst of the largest 100 cities).
6. The city lacks any prominent sense of community. Most people don't know their neighbors (although I'm sure there's the odd building or block for which this isn't true). It seems like the overwhelming majority of people are transient and isolated ("alone in a crowded city"). A lot of people seem depressed as a result.
7. Chicago's COL is only low by coastal standards. It's still quite high compared with most of the country. Of course, the present inflation crisis and likely recession are probably going to make these comparisons a bit messier until things reach a steady state.