I did that commute for a yr. I chose BWI because of train option to get home when NYC airports close.
MDW has non stops on us. To get to/from BWI you have to go off line. Delta has a 9pm out of JFK that’s always open. I’d take that for my AM flight the next day. For a PM report delta has. 8-9 am flight that gets you in in time. Also United has a flight out of EWR in morning that gets you in in time for PM RAP.
Coming home almost always was delayed. If an AM flight or reserve delta and AA had flights mid day and afternoon. The last flight out was the United at 1930 but sometimes it’s was on a dash8 100 so weight limited but I was only affected by this once.
Like I said when the NYC airports close in the winter there is always the train $80-100 one way last min. If you booked when you got schedule it’s around $40 and refundable so you could go that route. Train is awesome. 2:45 and never crowded. Can get to from train by free shuttle at BWI.
I only came home through ISP a few times. Our flights don’t correspond with train sched so definitely last option.
A few times we had a ferry to LGA. jumped on that. (Best option)

All that being said I moved to a base and wouldn’t look back.