At this scale probably. I don't know the details of the CBA, but I guarantee the guys don't fly economy, it business or above. I bet they also use to have a travel staff, to handle the booking not to mention last minutes change and delay.
Excluding injured players (or those returning for personal reasons, like family death or birth of child), players are nominally flying with the team.
While AHL and ECHL teams fly commercial, I believe the CBA mandates NHL charter flights.
It IS a competitive advantage to fly charter over commercial. No 60-90 minutes arriving early. No excess baggage fees for equipment. Dedicated security line and straight on to plane. And if doing crossing borders, the immigration/customs agent(s) often come to the plane.
The teams also can control the quality of foodstuffs on the plane served to the players, as well as the timing of any meals.
(Do you recall that the NHL teams in Europe for the European Premiere games were "stuck" there for a bit after 9/11. As they had charter flights, they actually returned a bit earlier than many other flights. Some teams even offered to transport a few Americans stranded in their locale back to US.)
wow - those are some weak graphics. 
