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Plane departs at 9:10pm? So 8:40pm boarding time? I'd be leaving to go to the airport at 5pm sharp and no later. From 5pm-12am, if you are still stuck in a taxi trying to leave Times Square for a flight at 9:10pm, good luck. Traffic stands completely still 15 minutes at a time, pedestrians do NOT give a fuck and will crowd on to the street and not even acknowledge what a sidewalk curb is. If they see the traffic standing they will walk no matter what, which leads to more congestion when the lights change for the cars to go.
Most of those "Go to the top of" only goes up at certain intervals and you have to line up for tickets. No way you can go to one of those and not have to leave after for a flight.
Not sure if you get the scope of how busy New York actually is, but I wouldn't be too optimistic on seeing anything more than one attraction especially when you have a lunch reserved.
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