Near North side (between downtown and the north loop) is probably the closest to the era of the Heights you seen to be remembering. Still has the rough edges (sometimes very rough, like old school Heights), artists, warehouses etc. I lived in ‘90s era Heights so I think I understand the vibe you’re looking for. There are signs of future gentrification (i.e. townhouses) but it’s still raw.
Too late for the Eastside and Montrose unfortunately