Nothing sad about watching 737 action at MDW
. As far as approach, you can sit and eat at White Castle on Cicero and the planes fly almost directly over head. The best place to spot at MDW
I have found to be TZ
's (WN's as of February) hanger. Awesome! Amazing how the 737's take more of the runway than the 757's to take off. So, if you have real good connections and can get in to a hanger, that is the ticket.
Most of the airport has blast fences, so spotting is not too good, unless you can get out to the end of "B" concourse. Then again, if you can get in a hanger, you can get in there.