All: Yeah I know it is tight, but I booked with miles and that was a choice, so I am sure it is a 'legal' flight. Our flight arrives from SXM at 6:35 pm and departs for Chicago at 7:59. AA also has a flight listed after that departing at 10:35 pm. (It helps flying into one of the world's busiest airports.) We also have Global Entry.

And I expect the schedule to change.. I have seen the posts about AA's schedule changes.