Chicago is the least stressful because of options ORD, MDW, drive, I once even took the megabus back....Never again. Downside is it’s a big club.
NYC isn’t terrible if your good with public transit. EWR is getting easier again with an additional 170 and swapping a 145 for a bus. Plus fedex as a last resort.
DEN would be great if it wasn’t so many 50 seaters. You can get to DEN by 7am and there’s a late swa flight home.
ATL might be the easiest I can think of mainline metal every hour pretty much between DAL and SWA. Best part you don’t have to switch trains except for the terminal train.
Dallas see all my complaints about Chicago with less service, not drivable and no public transit.
Good Luck! Stay away from the west coast as it’s less fun then trying to find street parking in Clayton.