January 25, 2016: Since airlines continue to find creative ways to rip off frequent travelers, we have to find creative ways to take advantage of their faulty, money sucking system. Fortunately, Industry insider, Rick Seaney, knows his way around the airline calendars and put together a list of the cheapest days to fly. Whether you’re visiting family a few states over, hitting the Caribbean shores this spring, or adventuring to the other side of the globe, be sure to shoot for these dates for the best deal possible.