I was born and raised on the SouthWest side of Chicago. The South and SouthWest parts of Chicago are full of native Chicagoans.
I think it is a great part of town.
The North side is full of transplants, that is anyone who want to move to “The City” from out of State, Suburbs or wherever moves to the North Side. The South side is easier to get around, there are more single family homes, 2 flats, three flats etc. Parking is easier because we are not wall to wall high rises, thus densely populated like the North side.
You can easily visit someone and find free on street parking on the South and South West Side.
Also driving on my side of town is a lot easier.
If and when I go up North or to the Loop (downtown) I take CTA (the transit in Chicago) because of all the traffic, lack of parking etc.
The South and SouthWest side are where you find real Chicagoans, many 2nd, 3rd or more generation. It’s where authenitic Chicago Food is.
The North side is trendy and has all trendy etc