Having lived in New York, San Francisco and Chicago for a minimum of seven years in each city and being a New Yorker by birth I feel I can give a fairly balanced answer.

New York - very aggressive and ambitious, life can’t exist west of the Hudson River, pseudo sophisticates only due to their spending, flock to the Hamptons because that is what sophisticates are supposed to do, send your kids away to prep schools because that’s what sophisticated people do. A lot of culture but mostly used by tourists.

San Francisco - not very aggressive or ambitious (ex Silicon Valley types), view CA as a country unto itself with the rest of the country being pretty irrelevant, leisure time a higher priority than other parts of the country (weather related). Plenty of culture but people are avoiding the city.

Chicago - pretty ambitious and work hard, but definitely not NY ambition or aggressiveness. People love the city in the summer where in NYC people exit as often as possible. Great museums, small theaters and music venues. Midwest values do exist as the people are really very nice and family oriented.

All three cities have great medical facilities and universities.

When we got transferred from NY to Chicago we weren’t happy but after a number of years there we decided not to go back to NY. SF was beautiful because of the weather and physical beauty but we didn’t like the CA centric attitude plus the governance.

Just my personal anecdata, the people I know from Chicago are cool. The people I know from NYC are meh. Everyone I know who moved from Chicago to NYC is miserable there.

I do not consider it unsophisticated at all. It’s the third largest city in the entire country and second only to NYC as far as an actual city vibe and feel.

Google hit for 'Chicago unsophisticated' got this juicy story. A billionaire and his now ex wife had an allegedly violent argument when discussing their pre-nup because she wanted the freedom to move to San Francisco or New York City in the event of a divorce because she found the Windy City “unsophisticated,” according to a court filing: https://www.chicagotribune.com/2015/02/20/ken-griffin-wife-found-chicago-unsophisticated/

The ex wife's bio: Born in France, undergrad at Georgetown, MBA from Harvard: https://en.wikipedia.org/wiki/Anne_Dias-Griffin

It is a midwestern town. So I assume people think this (I am from the Midwest).

I don’t really think about it. I’ve been a couple of times and found it nice enough—good restaurants and that kind of thing.

I think of it as geographically isolated, but not unsophisticated.

No.

What? No.

— East coaster

No, I don’t see it as unsophisticated.

No, I'm from this area and do not view Chicago as unsophisticated. My issue is that I have a bias again beaches that aren't ocean beaches

I come from Europe and all I know is that Chicago is supposed to be cold and windy.

To put it bluntly, where I come from, the US in general is thought of as slightly awkward and uncultured. That's not what *I* think. I love the US! But that is the perception. People don't make a distinction between the coasts and the middle

No. But I have cousins in Chicago and have spent enough time there to know that the terror of being thought less-than is a constant spectre for them. It's bizarre. Once while visiting from NYC I had a guy in a bar scream when he heard where I was from "It's not called the Second City because it's second to New York!" Yes, I know that, but now I also know this is a thing you're afraid that people think, which is odd.

Chicago is a world class city, filled with people who are concerned you might not recognize it as such.

Less sophisticated than the coasts but I wouldn't go so far as to say unsophisticated.

A work colleague based in Manhattan on zoom earlier today called it a gorgeous city "but unfortunately, it's rather unsophisticated." Others on the zoom nodded and chuckled in agreement, including people from Chicago who now live elsewhere.