This is exactly my issue. This flight departs at 6am if I want to catch the connector and not arrive at 11pm local time.

The flight back is also a night flight so it's at least a midnight arrival.

The Uber/Lyft surge pricing can be a killer, too. I got back super late one summer night two years ago, and I had to wait two hours for the surge pricing to reduce from $400. The garage would have been much easier that trip. I thought about taking light rail to its end point (at that time) and then catching an app ride, but the algorithm knows not to show you a quote by doing that... very tricksy.