There are very early flights, like 6 or 8 am but I'd be ok with 9 or 10 am. A 2 am Uber at O'Hare does not feel reliable to me. The flights home are on Saturday, so we don't have to be at work the next day or anything.
Problem is flights to CR are awful this year and $$$. I have booked flights to CR on SW from MDW and flights home on AA to ORD so we can't take our car either way. It would be a different airport.
ETA on closer inspection, all our seats are separate on the new flights and while I can be separate from DH, I'm not thrilled with DS in a middle seat with 2 strangers for 5 hours. I may just forget AA and pay the 53k pp on SW (omg 106k pp RT for SW
)