Leaving Oakland for Chicago or Toronto

I would move to Toronto.  Both Chicago and Toronto have violent crime but I would feel safer in Toronto.  https://www.nbcchicago.com/news/local/chicago-homicides-rose-by-139-per…

https://www.osac.gov/Country/Canada/Content/Detail/Report/6cffbda7-d425… your children become Canadian citizens, then the cost of college in Canada will be considerably less than the cost of college in the U.S.  The cost of medical care in Canada is less expensive than the U.S.

I lived in Chicago for 8 years and absolutely loved it. The winters are no fun, but you make it through. It's a bit segregated, but you can find neighborhoods that are more diverse; just be mindful of gentrification. Generally people are pretty open-minded and you can find pockets of progressiveness. For example, composting is not run by the city there, but you can find private services to do pickups. As for schools, I was never a parent there, but people generally found schools that worked for them. CPS has a bad reputation but I bet if you dig you can figure out which ones are decent. The best part about Chicago is the people are super friendly, so you can ask your neighbor which schools they like, etc. The food is excellent, and the whole city is bike-friendly!

Envious of your ability to move to Canada!  Putting that to one side, I can speak to Chicago, as I grew up there (ages 3-10 in Oak Park, then 10 through college in the city proper).  For me, Chicago was a great place to grow up.  As lots of people say, it's a city of neighborhoods -- many ethnic enclaves with first- and second- generation immigrants.  Food-wise, I'd put the Bay Area narrowly ahead only because we are able to eat so many fresh fruits and veg year round. But in terms of variety and affordability of ethnic food options, Chicago may actually have a narrow advantage!  Chicago is a city with a strong commitment to maintaining public spaces, including miles of lakefront for biking/walking, swimming beaches, and huge downtown parks with kid-friendly activities once COVID ends (skating, playgrounds, public outdoor concerts).  Great transit; I didn't learn how to drive until I moved out to California. Chicago also has an extensive magnet school program, which continues through high school, and which I attended (my parents actually moved into the city from the suburbs so my brothers and I would be eligible).  While I have some political reservations about magnet schools (the podcast Nice White Parents does a great job of breaking down how these schools serve white students at the expense of Black and Latinx kids), I am incredibly grateful for my experience in the Chicago Public Schools.  My high school was racially and socio-economically diverse, drew kids from the whole city, had really strong art and music programs, and -- despite having a decent chunk of kids go to top-ranked colleges -- never felt particularly competitive.  That may have changed in the intervening 20 years, but there are 5-6 similar high schools throughout the city.  In many ways, my brothers and I grew up like NYC kids -- navigating the El by ourselves, spending lots of time downtown with our friends (because they lived far away from us), using student passes at the museums -- but our parents could afford a 4-bedroom house (albeit on the far west side).   

Politically I think Chicagoans are less identity- and enviro-focused in what issues have salience, and less performative than Bay Area (which I appreciate, ha) but very progressive.

The biggest downside for me -- what I feel like I'd miss out on raising a kid there versus here -- is easy access to nature.  There are some regional parks for day trips and if you have the money and vacation time you can take road trips to national parks, but there just aren't the opportunities for hiking/camping/etc. and it's not really part of the culture there.  

I also want to acknowledge that my experience was that of a white kid with professional (but not wealthy) parents and that the city continues to suffer from brutal policing, redlining, and disinvestment (including several rounds of school closures in predominantly Black south side areas) -- as do most (if not all) American cities.  But despite frustration with the city's leadership, folks of *all* backgrounds I've spoken to who grew up there deeply love it and are working hard to make it better.

Ugh, we have finally reached the point where we are considering a similar move.  There are very few places where one can truly escape the worst effects of climate change, at least in the long run.  Chicago certainly has its share of challenges ahead too, but for us the seasonal wildfire smoke is making Northern California truly uninhabitable, as we have a respiratory condition in our household.  So we are also very reluctantly but very seriously contemplating throwing away everything we've built for ourselves and our family after spending more than two decades in the Bay Area and hoping to live here for the rest of our lives.  But to answer your question... I think that Evanston is a good place for you to be zeroing in on, as it certainly has a lot of the things you've listed as important and at least in the experience of our friends & family, the public schools there are outstanding and pretty diverse without being too pressure-cooker-y.  Good luck to you, we are likely following in your footsteps soon.    

Check out Oak Park, right outside of Chicago! It's on the "L", so easy access to downtown/lakefront, and it is fairly diverse with good schools. I lived in Chicago as a childless adult and it's my favorite city. Chicago has an interesting school set up--kids can apply to be in a variety of schools.  I worked with some of the high schools when I was there and there are several good ones. Good luck!!

I grew up in Toronto, have lived here in the Bay Area for over 20 years, and I still go back frequently.  I assume that your thoughts about Toronto probably include the sprawling suburbs where the public schools are probably more coveted?  Your kids may benefit the most if they get into the many public special programs from a young age.  Ontario's olympic athlete training+schooling programs are amazing from what I hear.  French immersion schools will only accept students from the ground floor.  Public magnet gifted programs still exist in some school districts.  The friends who stayed in Toronto proper have their kids in private schools or a public French immersion program.  I think folks in Toronto are more open minded because with the exception of a very few tiny WASP enclaves, black people do belong as much as Asian people, as much as any other person of color in any given neighborhood.  On a regular basis you will have a greater chance of encountering genuinely kind people who for some unfathomable reason are thinking about your best interests (vs just thinking about themselves).  Your kids will probably not grow up being fearful, untrusting, or expect less from themselves or any other person, regardless of race.  I suspect that downtown Toronto is still considered very safe after dark.  My parents had no issues with me going down there with my friends to shop, play, or for special events.  There is the occasional encounter with the mentally ill but there are so very many people on the downtown streets at night that it is was not a problem and probably still not a problem.  Toronto is a remarkably clean and proud city.  Good luck.

I grew up outside of Chicago, went to school in Chicago and lived there as a young adult. I have many friends and relatives still there. I think Chicago is a fantastic city. I love it. But Illinois is in a terrible financial hole that’s even worse than CA’s. My friends complain that their taxes have skyrocketed but services are being slashed because of under funded public pensions. One good friend has moved out of state b/c of this. Several sold their homes and switched to renting to avoid the property tax increases. Several are just waiting to get their kids through college before they leave. If I moved to Chicago one thing I’d probably do is rent not buy. On the other hand, house prices, particularly in the suburbs, have not appreciated in over a decade, so you might be able to buy a pretty nice house for not a lot. 

I hear you on all of these concerns — we just had our first baby in July and she has spent half her life indoors avoiding smoke!  I grew up in Oak Park, a suburb just west of Chicago, and went to grad school in Evanston, and I think they’re the two Chicago suburbs to consider based on your criteria.  Oak Park is by no means perfect (there was actually a Starz documentary about the high school called America to Me) but they do value diversity and strive to always do better.