Eat at the bar
There are lots of places where you can eat at the bar. Two in the Loop that come to mind are tesori (Italian cuisine, the bar in the dining room is a granite counter facing the open kitchen so you can watch them prep the food; they also have a separate room in front with a bar that's primarily for bartenders making drinks) and the Florentine (also Italian cuisine, the bar is a large island in the middle of the room that's primarily for bartenders making drinks).
>> My ideal would be something like tipsy parson in NYC
Can you describe the kind of place that your ideal is like?