Thanks everyone!
Those are the answers I expected. Maybe, If, stars aligned, and yes.
The issue is we like to fly in and out of a smaller airport closer to the house and avoid LGA and JFK. The next one is 6:30 PM and we'd rather not have to kill a day waiting in the airport so I wanted to gather other people's thoughts. I'm a "need to be there two hours before" kind of person and it will probably stress me out if we go that way. Maybe will just fly back to NYC and avoid the stress.
Thanks again for taking the time to answer.