Quote Quoting Mr. Knowitall
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JFK is a very busy airport. Check with the customs office to determine the hours of passport control for the night of your arrival. The easiest option may be to wait out the two hours and fifteen minutes before going to passport control. You can try earlier and see if the entry officer allows you to enter a couple of hours early, which is not outside the realm of possibility. Entry as a tourist followed by adjustment of status or working unlawfully then leaving and re-entering, seems a lot more complicated than spending a couple of hours reading a book before trying to enter the U.S., and there's obvious risk to working unlawfully after entering on a tourist visa.

If you want to know the policies of your airline for boarding the flight, you will need to inquire with your airline.
Hi, thanks for your answer! Actually the idea of entering with the Esta and then get to Canada and re-enter with the H1B did non imply any unlawful work, since I will not officially start working until August 22. And actually I was not thinking of changing my status, but simply get the Esta together with the H1B., and then forget the esta once I am in with the H1B. My first idea - and probably the one I would follow - was the one you suggested me. I am only afraid that the flight attendant, at the check in, would not let me board on the plane. Do you think it might be possible? or I am just overthinking?