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Why the Best Holiday Travel Comes Before the Holidays

PORTLAND, Ore. (TheStreet) -- Every year, I sit down with travel experts and listen to them advise my readers to take advantage of "dark" weeks on the holiday travel calendar and book trips when other travelers typically don't. Every year, I wave those same readers farewell while remaining shackled to my workstation, never taking those recommendations myself.

This year, that that unfortunate tradition comes to an end.

My wife was assigned to four days of training at the Centers For Disease Control in Atlanta by her lab in early November and didn't want to take the trip alone. After years of hearing my father's stories about his own trip to Atlanta during his days with AT&T (T), it seemed like a good place to keep myself busy during the day and meet up with my wife for dinner at night after she'd finished her day of training.

In early November, we booked tickets that took us out of Portland on Dec. 15 and brought us back on Dec. 19. Her lab got her a flight on Delta (DAL) while I found a direct flight on Alaska Airlines (ALK) that came in at $250 less than the Department of Transportation's average fare for the two destinations. When we arrived for our flights that were scheduled to leave at roughly 9:30 a.m. on a Sunday, we found Portland International Airport looking far emptier than when we'd taken flights to Philadelphia out of it at 6 a.m. on a Saturday just a month earlier.

It would be a stretch to call the airport dead, but it wasn't exactly bustling either. I made my way through security in less than 15 minutes, was able to get a cup of coffee without snaking through lines and found a seat with outlets for laptops and device chargers without having to squeeze in.

Despite this, my Alaska flight still had concerns about accommodating everyone's carry-on luggage. I'll never advise using a carry-on to avoid baggage fees again, because it's clear every traveler in the U.S. has received that message. What they may not realize, however, is that their glut of carry-ons has created an even better perk for the average U.S. flyer: Free checked luggage. Without fail, folks at the gate will point out that everyone is wheeling a larger carry-on onto the plane, stuffing all of the overhead compartments and making boarding an exiting a protracted nightmare.

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