Anonymous wrote:OP here. Thanks for all the odes to Chicago but honestly, if we moved, we'd be a family of 4 with two small kids. We aren't going to be having regular meals at the chic restaurants, nor going to baseball/football/baskeball games, etc. Personally, I know 2-3 friends who LEFT Chicago for other places for lower-key pace of life. They lived in the city, but once they had 2+ kids, didn't want to deal with city living and schools and didn't want to start over moving to the 'burbs. I would love to hear from people with families talk about family life in Chicago.
Right now, we have a decent lifestyle by DC standards. I don't need a bigger house (we bought 10+ years ago and have re-fi'ed), our kid(s) are in very good JLKM schools, we have an easy 20-40 min commute to work. So most of the reasons people have for fleeing DC don't apply to us.
I'm 30, and ~20 years ago my parents were faced with the same choice you are making. We had a good life in NW DC, we were in a good JKLM school, generally happy with life, my parents had short commutes, etc. but my dad got the opportunity to transition from working in the government to working in private practice which he really wanted to do. Added to our situation, my dad's family is all in the Chicago area, which was a plus (although my mom grew up in the DC area, so we were already near one set of grandparents). They made the decision to move, and my parents love Chicago.
We grew up in Wilmette, which is not a crazy commute downtown, especially by Metra. It has access to both the Metra and the El, an excellent public school system, and it is pretty and leafy with a park district that has a lot of well organized activities. We did get the opportunity to take advantage of some of the cultural opportunities growing up (art institute, the aquarium, etc.) although we were the sort of family that generally did that because we spent a ton of time at the Smithsonian in DC. There are various issues with living in an affluent suburb that would happen in any metro area in the US, but it was a perfectly lovely, safe place to grow up. When I was a teenager, I really appreciated access to public transit so that I could escape suburbia (although frankly, we were 15 miles from downtown and less than 5 miles from the city limits, so it wasn't the desperate deep suburbia I thought as a dramatic teenager). Evanston and Oak Park are often considered good options if you want a more urban suburb with a shorter commute, but don't want to deal with the hassle of city schools. Like other cities, people move to the suburbs when they don't want to deal with the hassle of navigating an urban public school system after elementary school with the choice of evaluating a very small number of potentially acceptable open enrollment high schools, navigating test-in magnet programs, or deciding if private school is in the budget.
There are plenty of nice neighborhoods in the city and in suburbs to raise a family in Chicago, and a lot of cultural benefits to being in a big, vibrant city. But, DC is also great. I think you could have a good life in either place (we certainly did!). This decision for you really comes down to balancing the professional goals of you and DH.
The cold is indeed brutal, and I try to avoid living in the Midwest and Northeast for this reason. But, you buy the appropriate clothes and keep on with life. There are a lot of cities people move to where winter sucks (New York, Boston...)
Now my parents are empty nesters, they spend a ton of time going to chic restaurants, cool art shows, cubs games, sailing their little sailboat on Lake Michigan, and enjoying all the stuff that seems irrelevant to your life situation right now.