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[quote=Anonymous]NP. I have lived in Chicago and DC (and Wisconsin, actually, but that was a while ago) -- in both cases, in the cities themselves. My kids, when I was in DC, weren't of school age yet but I still have lots of friends with kids in the DC schools now. When I lived in DC, I worked in an office downtown but now I work from home in Chicago so don't have apples to apples commute comparisons.

Friendliness of people -- I personally think that's a wash. DC people tend to be very smart, and I always really liked that at any dinner party, you'd have someone interesting to talk to. Everyone has traveled a lot, the city is racially diverse (although economically segregated and there are obviously racial implications there). I made life-long friends in DC because they're kind of "my people" -- extremely educated, a little sarcastic, "worldly." In Chicago, people are warmer and I have found that my social network is much more racially *and* economically diverse (although I live on the south side, not sure that would be the case if I lived on the north side). But that kind of "Minnesota nice" is real -- it can be hard to get truly let in, and sometimes I feel like my guard is up. My best friend here, who I really adore, didn't even know what my job was until 3 years into our relationship. Our friendship is based around our kids and shared non-political interests. I have a much longer list of friendly acquaintances and early friendships here than I did in DC, and am much more likely to run into someone at the grocery store. Similarly, cashiers at my local restaurants and libraries and the post office recognize me and are likely to joke around, although in a very casual way. That never happened to me in DC. The bad thing about DC friends is that they are almost always a flight risk. Of my best friends in DC, 75% of them have left the region. Oh, and politics is a thing worth mentioning -- DC is very liberal. So am I. So is Chicago. But politics is close to the heart of a lot of people in DC in a way it isn't anywhere else in the country, so it's a very common topic of conversation.

Hustle and Bustle -- Chicago is famous for its bad traffic, but I find that it is MUCH better than DC. DC has no major in-town thoroughfares -- I remember constantly swearing while driving down Georgia because of all the damn uncoordinated traffic lights. It would be infuriating, taking 25 minutes to go .25 miles. Chicago is easier to get around, IME, and there are always "alternatives" to the major clogs on the highways. The public transportation in Chicago is vastly superior. In DC, the metro is the best bet but it has some serious issues and doesn't have great coverage of the city. Definitely nothing like London. People tend to drive places. The really noticeable thing about DC is that since so many people work 9-5 office jobs, getting something like an oil change or going to Costco on the weekend can be an absolute nightmare because EVERYONE does it on the weekend. If you're going to SAH, that will be a nonissue since you'll be able to take care of things like that when other people are working in their offices. I have nightmares about trying to get out of the Arlington Costco parking lot during rush hour in December.

School competitiveness -- basically the same, from what I hear. In Chicago, there's a lottery and a testing system (not the case in DC, just a lottery for most schools). Rich people in both areas often go private, especially if the lottery fails them. Kids in both cities are pushed into extracurriculars of all sorts.

Anyway, I could go on, but those are my thoughts. There's also a quick covid note -- DC people are uber cautious. That'll be new to you if you're coming from Wisconsin. 
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