The main problem with Chicago is it lacks an anchor industry. Is it the best place to be for finance? No, that's NYC. Is it healthcare? Boston, Baltimore, Cleveland or Rochester. Energy? Houston. Technology? SF. Entertainment? LA or NYC. Politics? DC.
What exactly is Chicago good at? They have Wilco, so that's cool.
There are a massive number of other companies headquartered here, like Boening, CNA, Kraft Foods, Walgreens, State Farm.
While NYC might be known for its comedy, it recruits directly from Second City in Chicago, and the numerous small comedy clubs and schools here feed into Second City. It has its own caliber of theatre it puts out as well, regardless of whether it matches NYC on notoriety.
Lastly, while having the benefits of a large city, Chicago also does not have the stupidly high rents of NYC or SF. It is a very livable city, even for those on modest incomes. Public transportation is excellent (though not as good as NYC).
And if you are doing well enough to have a six-figure salary, you can live very well here as opposed to how you would live even on an cost-of-living adjusted salary in SF and NYC.
The primary downside to this city is the weather. In my opinion, the secondary downside is how far it is from outdoor activities, but, then again, you can easily fly elsewhere via O'Hare/Midway.
I grew up and lived in Chicago for most of my adult life. I moved to the Bay Area in 2013. My main reasons were weather, crime, and jobs.
For some people, living with gray skies half the year with not-infrequent temperatures below zero or above 100 takes its toll. Also, the violent crime rate has gone through the roof in recent years, even in generally good neighborhoods.
On the jobs front, I'm in marketing and a more technical marketer at that. The job options in Chicago were largely unappealing, but more importantly was the major difference in culture. There are obviously exceptions, but Chicago seems to have a much more "conservative" corporate culture on the average. This means less competitive pay, 2 weeks of PTO, 2 weeks paternity (if that), stricter 8 or 9am start times, less free on-premise food, fewer perks overall, less competitive benefits, etc. Again, you can find exceptions, and large tech companies tend to have offices there as it is a hub (particularly for media companies like Google). But on the balance, due to the extreme concentration out here, it seems many Bay Area companies are forced to up their game and be much more in favor of the employee with regards to comp, perks, culture and benefits if they want to be competitive with the local giants.
I get very sad when I think about the cost of housing out here, but TBH, I'm not sure I could go back. Whenever I get off the return flight from a trip home and step out the doors at SFO, all of the color, sunshine etc. makes things look like technicolor compared to the ugly red brick, gray skies and black slush of Chicago.
Don't get me wrong--it will always have a place in my heart and I dearly love many things there. But depending on your priorities, in some cases there is no competition if you can afford enough to make it manageable.
This is a weird expectation. Why does a city have to be "the best" at something? Seattle isn't the best place for software but I'd still choose it over SF any day. Chicago has plenty of industry.
Also, not too many people aspire to be in insurance. I don't think you can put it on the same level as finance, arts, software, fashion, film, etc.
Do people aspire to work in health, energy or finance, or even software aside from the money? If so, what difference does it make?
The whole situation is dumb, overall I'd avoid living in CT for a ton of reasons. CT had a lot of industry going for it (Stanley Tools in New Britain, for example, and Hartford was the center of the gun industry 100 years ago) but those of course moved overseas. The insurance industry provided a safety net so it didn't go the way of the rust belt but, late capitalism y'know, so that was just a band-aid that's being slowly ripped off. This is happening everywhere but the systematic denial isn't as ingrained as in CT, it's weird.
Aerospace/Defense: Boeing
Agribusiness/Foodservice: ADM, Mondelez, McDonald's, US Foods, Ingredion
Communications: Anixter, Motorola, TDS
Energy: Exelon
Finance: Discover, JLL
Healthcare: Walgreens, AbbVie, Abbott, Baxter, Baxalta
Industrial/Manufacturing/B2B: ITW, CDW, Navistar, Grainger, Univar, Tenneco, LKQ, Dover, Packaging Corp., Essendant
Insurance: State Farm, Allstate, Old Republic, AJG
Publishing: RR Donnelley
Retail: Sears
Transport: United
If you intend to create technology for supporting businesses in those sectors, having a Chicago office would not be a bad idea. SV unicorns tend not to even want to solve problems like how to more efficiently route a single gigantic monolithic I-beam from the foundry to a building site without destroying buildings, bridges, and roads along the way. It isn't sexy, and doesn't attract money or eager and idealistic employees.
As far as entertainment goes, it's no accident that a huge number of comedians get their start in Chicago.
Chicago has tons of anchor industries, the real problem is that they don't translate well to the unicorn strategy of most start-ups.
https://en.wikipedia.org/wiki/Economy_of_Chicago
>Chicago and its suburbs, which together comprise the Chicago Metropolitan Area, is home to 29 Fortune 500 companies and is a transportation and distribution center. Manufacturing, printing, publishing, insurance and food processing also play major roles in the city's economy. The total economic output of Chicago in GMP totaled US$547B in 2012[1] making Chicago the 21st largest economy in the world[2] just surpassing the total economic output of Switzerland.
>The city houses one of the Federal Reserve Banks, established in 1914. There is also the Federal Home Loan Bank of Chicago. The largest banks in the Chicago region (by % of deposits) are: JPMorgan Chase, Bank of America (through its acquisition of LaSalle Bank), BMO Harris Bank (a BMO subsidiary), and Northern Trust. The largest banks headquartered in Chicago are: Northern Trust, Chase, BMO Harris Bank, Wintrust Financial, and First Midwest Bank. Many financial institutions are in the Loop.
>Chicago has five major financial exchanges, including the Chicago Stock Exchange (CHX), the Chicago Board Options Exchange (CBOE), the Chicago Mercantile Exchange (CME), the Chicago Board of Trade (CBOT), and NYSE Arca. While the city of Chicago houses most of the major brokerage firms, many insurance companies are in the city or suburbs, such as Allstate Corporation.
I have family in Rochester and it isn't known, at least to me, for healthcare in particular. The biggest Rochester companies are Xerox and Kodak neither of which are healthcare companies.
Geography.
Chicago's the primary water connection between the Great Lakes (which communicate with the Hudson and St. Lawrence Rivers) and the Mississippi River; that's the historic origin of its central role in commodities trading.
Corruption.