I have a flight from DEN --> LGA, arrives LGA at 9:30pm on a Friday. I am wondering if it is possible to make an 11:00pm flight JFK --> BOS later that same evening.

I know it will be extremely tight, but am trying to get a sense of if it's at all possible. (I can't change the flight into LGA and there are no late flights from LGA --> BOS). I won't be checking any bags and am fairly familiar with both airports/taxi stands/ticket counters/etc.

So I'm wondering: 1) Does anyone do DEN --> LGA enough to know if flights are generally on time on Fridays and/or in the summer? 2) Does anyone do the LGA to JFK via cab frequently enough to give me a time estimate they've found to be generally consistent? 3) What are the security lines like at JFK on Friday nights in the summer? Thanks!