This is the Chicago block I grew up on. It's less dense than Oak Park. It's easy find blocks like it elsewhere in Chicago. Jeff Park in Chicago and Oak Park are basically clones of each other.
This is really what most of Chicago looks like (modulo economic conditions in the different neighborhoods --- they're not all this upscale). It's a city of neighborhoods. Most of the streetscapes that jump to mind about Chicago, if you don't live here, are places people basically don't live.
Wow, you weren't kidding about the relative density between those areas. I'd consider Oak Park dense compared to most suburbs, just not as dense as some neighborhoods in Chicago. I'm most familiar with the north side neighborhoods and had those kind of lots in mind, with their near non-existent front yards, with front steps right off the sidewalk, and virtually no front driveways.
Apartment building on Pine Grove in Lakeview for me and then a beautiful old two flat in Ravenswood. My rent in Pine Grove in 1999 was $400 I think for a two room apartment.
Small world, my wife and I literally just moved to Beverly not far from there. This area is a bit of liminal space between city and suburbs (or at least my definition of them) and it can vary quite a bit block to block. I'm walking distance to a grocery store, the Metra, coffee shops, restaurants, parks, etc., which is unfortunately more than many areas of Chicago can say.
I moved from a denser part of Bridgeport, so it definitely has been an adjustment (particularly in variety). But even some areas of Bridgeport, which is much closer to downtown, had pockets that are equivalently walkable to where I'm at now, or maybe even less so. Anyone surprised to see SFHs and front yards in Chicago probably hasn't ventured far out of downtown/a handful of North Side neighborhoods.
https://www.google.com/maps/@41.7099143,-87.6801127,3a,75y,1...
This is really what most of Chicago looks like (modulo economic conditions in the different neighborhoods --- they're not all this upscale). It's a city of neighborhoods. Most of the streetscapes that jump to mind about Chicago, if you don't live here, are places people basically don't live.