Travel Heading home for the holidays? Here are the cheapest day to fly, from a travel economist. October 26, 2022November 3, 2022Clare Mulroy, USA TODAYComments Off on Heading home for the holidays? Here are the cheapest day to fly, from a travel economist. Tuesdays and Wednesdays are the cheapest days to fly. The cheapest holiday travel days are Nov. 21, Thanksgiving Day, Dec. 19, Dec. 20 and Christmas.