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I'm currently a rising 3rd year securities/M&A associate in the Boston market, contemplating a move to Chicago. I've lived in Boston and NYC for my entire young adult/adult life and am looking to set down permanent roots (at least for the forseeable future, think next 10 years), and aside from NYC, Chicago is the only other serious consideration for me right now. If you live and work in Chicago's market, could you share your impression of the general firm culture there or if you have any relevant experience transitioning into Chicago's market? Things you wish you had known about the market (or the city), good or bad?

(Background: I don't have any ties to Chicago other than friends, I want to move there mostly because the quality of the city I live in is important to me, Boston isn't cutting it and Chicago was incredible and everything I wanted in a city to live in.)
*Anon because based on this post and my other posts, folks could easily figure out my firm...

I've been in Chicago for about a decade and work at one of the city's top firms. I've also done some time in NYC.

In general, Chicago is a much more relaxed market, and, at least at my firm, people get out of the office around dinner time and go home. Now, a lot of them get online during the night and continue to work, but it's much less like my time in NYC where I'd leave much later and there would still be a fair amount of folks in the office until ten or eleven.

The deals you'll work on will probably, on average, be smaller, but I wouldn't care too much about that. They'll still be objectively huge deals, and they'll still be very important to your clients' businesses.

As you know, the CoL difference is massive. It was immensely easier to build a emergency fund (that could also be significantly smaller due to far lower CoL), get a down payment on a nice place, save for retirement, and enjoy the city. Personally, I hated paying $2k a month to live in a closet in NYC. I hated eating out in Manhattan and feeling like I was getting robbed. Etc. In Chicago, that's just not a real problem.