It’s probably worth pointing out that historically the majority of the wealthiest pockets of Chicago were on the south side. There are a lot of grand streets with magnificent homes, broad sidewalks with enough space for the tree canopies to develop nicely, etc. All that exists on the north side too, just not as frequently. And where it does it’s 2-3x more expensive.

There’s a couple streets down in Kenwood that I don’t think have any equivalent on the north side though…