Santa Claus will start Billings flyover at 5:15 p.m. Christmas Eve Q2 News / Mitch Lagge The lights that comprise Santa's reindeer await their flight around the city at Billings Flying Service Wednesday. and last updated 2020-12-23 20:11:55-05 BILLINGS â Santa Claus will make his annual flight around Billings, Lockwood, and Laurel starting at 5:15 p.m. on Christmas Eve, a source close to the Christmas icon told Q2 on Wednesday. Since about 1980, Santa has gotten a bit of help on his journey from pilots with the Blain family, who own Billings Flying Service. The company's pilots are usually out fighting wildfires or lifting heavy objects into tight places, but their part-time job is to spread cheer on Christmas Eve.