Tent caterpillars feed during the day, so maybe try pay attention to when the damage is happening. I assume Chicago would have similar bug risks as central Canada.
The hook in the bite on the right-most leaf looks like caterpillar, as they lay along the edge of the leaf and move their head down to eat until it curls back up to reach their body. But the upper left leaf in the picture looks more like a tear than a curved bite. You could have a few different things attacking it, but the majority of the damage is curved.
Are there any strands of silk anywhere on the plant, particularly the forks of the branches? Can be hard to notice unless there's a bunch of them.
Googling for leaf cutter bee damage pictures, they seem to leave damage with both edges round. Same with the ants.. The pictured damage seems less "circley".
You could try putting some sort of home-made glue trap around the base of the plant. If you inspect the plant and decide there are no pests on it, then cut off the ground-based approach, you're only left with air-borne pests.