Advice about Moving to the Midwest

I grew up in Evanston, IL and it fits a lot of what you described.  Its a university town, with Northwestern there, and quite diverse and liberal with an easy train or El ride into Chicago.  My knowledge of it is a bit dated, but I loved growing up there.

You should check out Ann Arbor, Michigan! It meets all of your criteria and has a wonderful community. Good luck! 

My mom is from Evanston, IL and I grew up visiting during the summers and then also during Thanksgiving and wintertime. I'm not sure about the recycling, etc. part, but this city checks all the other boxes except maybe when it's snowing/too cold to be outside for too long; I don't think their winters are typically as bad as some other Midwest/East Coast cities though. It's a beautiful city and right on Lake Michigan.

Hi there! I would highly recommend Evanston. It has racial diversity, college town, safe, very good neighborhood vibes, close to public transportation and most schools there are good. It's very liberal. I love all of the northern suburbs along the lake, but you get less diverse as you go up the shore -- Highland Park and Wilmette are awesome, for instance, but 98% white (Evanston is more like 70%). I personally know several families who live in Evanston (and I lived there too!) I also know the mayor of Highland Park really well and she is fighting for more diversity and equality - happy to put you in touch if you are interested. I will note that I am biased as I am a Northwestern grad :). The burbs get a lot more conservative as you head away from the lake. 

I can't think of any towns that fit all that criteria (esp. "lots of outdoor activities year round"--midwestern winters can be pretty harsh, as you likely know already) but from experience Iowa City, Iowa and Madison, Wisconsin might be worth looking into. Madison does have more diversity as it is a city, not a town, but has neighborhoods within it that are more "town" like and self-contained. I can't speak to the school situation there, though. Iowa City is smaller but it and nearby Coralville have a decent range of ethnic restaurants--and the presence of the University of Iowa lends cultural richness, so the city is less white than Iowa as a whole. That said--still pretty white. It's a liberal island in a fairly conservative state. Has the best bookstore in Iowa (Prairie Lights) and good K-12 schools. Cedar Rapids airport is near so flying in and out of Chicago is an easy, short flight. Good luck with your search!

Sounds like Madison to me!

But there are other college towns that would fit a lot of those categories - with the racial diversity being the most challenging on your list. Sure, many college towns are moderately diverse, but not compared to here. We are a mixed-race family, which is more rare in parts of the Midwest. I've also lived in Urbana, IL- which is has more of a smaller town feel than Madison, but if your jobs aren't affiliated with the University, there are less opportunities.

Check out Evanston and maybe Oak Park. Not sure about "outdoor fun year round" -- when its 20 below, that may feel less appealing.  ;-)

Hey! My husband and I grew up in Evanston, which is just outside of Chicago. It's got pretty much everything you're looking for. I'd check it out. If my husband's job wasn't so completely Bay Area-focused, I'd move back there in a heartbeat. It's a great place to grow up and live! If you want to ask any questions, you can email me at joey.harmon [at] gmail.com

Evanston, Oak Park

Best place to live would be Evanston, Il 

Hello, I moved here 2 years ago after 12 years in the Chicago area. A few things I think may be helpful:
~ By good schools do you mean public? If so, there are great public schools both in the city and burbs HOWEVER:
~ If you go public, and want some diversity (it will be less than the Bay Area esp black Americans - Chicago is still very segregated), I'd look at Oak Park, Evanston and Hyde Park. I love all these neighborhoods. Hyde Park is where Obama lived and U of Chicago. Oak Park is famous for Frank Lloyd Wrights home and studio, and pretty "liberal" by Midwest standards. Evanston is on the lake and gorgeous, good public schools and some diversity. A little pricier than Oak Park and Hyde Park. 
~ All the above, and city neighborhoods are walkable for the most part, but biking is biggest along the lake (lake trail). 
~ Portage Park is up and coming and super cute (so is Logan Square)
~ Once you get further out of the city (true suburbs like Naperville, Winnetka, etc) you'll lose the diversity and liberal leanings.
 
Hope that helps! Diana 

Many such places exist! In fact, I'd argue they're easier to find--and much, much more affordable--than in the Bay Area. Except maybe the "outdoor fun year round" part--depends on your hardiness for extreme heat and cold and how attached you are to mountains :D. 

Basically, look for college towns. Champaign-Urbana, IL; Ann Arbor, MI; Madison, WI; Bloomington, IN; Oberlin, OH (very small). I've never been there, but have heard Lincoln, NE and Iowa City are nice (maybe not that diverse).

You didn't mention if you're looking for urban, small-town, or suburban environment. If you want a city, Chicago has a lot of what you want--schools can be an issue, but city that size has a lot of different options. Some of its suburbs might be options. Milwaukee--similar, though smaller. Pittsburgh (if you consider that Midwest) has quite a buzz around it in recent years. Cincinnati seems to have a lot going for it (not sure about schools). 

General advice: don't carry coastal attitudes about "flyover country" in your search. That's just baggage--drop it. The Midwest is rich, diverse (ethnically, racially, politically). A lot of progressive, social-justice, and sustainability ideas and movements have emerged from the Midwest and continue to do so. And I found the places I lived in that region much more community-oriented than the West Coast. You get out what you put in. 

Check out Evanston and Oak Park Illinois.

I grew up near Evanston. It might check a lot of the boxes you mentioned. I also have friends who live in Oak Park and it sounds similar to what you’re looking for.

Good luck with the move!

Evenston! Hands Down!

Without a doubt.

Well this isn't super close to Chicago, but you mentioned the midwest - Cincinnati seems to have an artistic diverse vibe. One area that appears really cute and walkable but may be too urban if you have a family is the Over-the-Rhine neighborhood, with tons of cafes and shops that is also walkable to the downtown with its main library and other cultural things. 

Right across the river (still walking distance or biking) is Bellevue KY. I had never thought of either of these places but a vlog I watch on youtube sometimes about an alternative family ("Fight for together") who live in Bellevue revealed how interesting the area is but not yet cutsified. Look at a few of their youtube videos, they walk to places or jog so you can see how easy it is to live there - both on the KY and Cincinnati side. Not sure on the weather but they pretty much live like that all year so somehow manage it.

Seems like a lot of arty types around. I also came across this BBC bit on a family living in Cincinnati during covid and it also shows it has an interesting group of people there https://www.bbc.com/news/world-us-canada-52358591

I have also heard good things about Fort Wayne IN - not for alternative or artsy but just affordable and safe. Doesn't sound like the downtown has yet revitalized but is undergoing some.

It sounds like a college town would be up your alley. If you want to stay close, check out Evanston, IL. It's a suburb, but has a pretty dense walkable downtown that feels like a small city. Other northern suburbs are nice too, but I think Evanston is maybe the most progressive? I lived in Chicago 10-15 yrs ago, and Chicago itself tends to lean very democrat, but it's a different kind of liberal than, say, Berkeley... not really environmentalist or anti-capitalist at all. If you can go a little farther, consider Madison, Ann Arbor, or Minneapolis/St. Paul (not really a college town, but very progressive).

I have no idea what "people who value anti-capitalism" means, but to your other points, I'd consider Evanston and Oak Park in the Chicago area, which is where I'm from originally.  Elsewhere, consider Madison, Ann Arbor, Iowa City, and the Twin Cities.  I've also heard great things about Columbus, OH.

We just moved here from St. Paul, MN. It's pretty liberal, quite diverse (my kids went to our neighborhood public school where students of color comprised about 50% of the children), and really green (we lived by Como Park, which has a lake, zoo, conservatory, and a small amusement park).  We loved our neighborhood but I will tell you, once you go outside of the blue bubble of the Twin Cities, not even 10 minutes out you will encounter Trump signs, racist folks (yes, I am a POC and my POC friends/family and I regularly encountered it inside and outside the cities), bigotry and many, many small-minded people who have never been outside of MN.  Just being real. 

I was thinking Evanston and Madison as I read these responses. Thought this may be of interest:
https://www.google.com/amp/s/www.apartmenttherapy.com/evanston-illinois-guide-32252469%3famp=1

Ignore the folks who caution you won’t be outside, simply isn’t true with kids especially. Yes it will be different activities but warm layers have changed greatly and now are so much less bulky—be sure to outfit yourself well too so you can be out with your family. No it won’t be 68 and sunny in January but it was always amazing to me how “warm” 38 and sunny can feel and that fresh air feels amazing! 😊

You will find like minded folks and though you may not check off all those boxes, maybe you can bring that change to an open and receptive community or those needs/wants may change once you are out of the Bay Area. 
 

All the best!