Southside nikkas was the same way.
At least on the south side, some parts have been able to maintain some sophistication. Virtually none on the west side.
Although, West Loop looking like its continuing to push its boundaries further past Ashland to Western and beyond.
Washington Park is not sweet, at all. Yeah they got a few things like the art gallery and currency exchange cafe on 55th and a few other restaurants but I wouldn’t venture further south than that at night. I’m down in WP st least once a week and typically try not to be there past 6pm especially near South Michigan(Murder Row)/Indiana/Prairie between 57th and 63rd.
OP make sure to hit up Randolph near Halsted in the West Loop. Some of the best acclaimed restaurants in the city are there. Go sailing on the lake. Best views of the city are actually from the water.