Life·4 min read

Up, Up and Away: How to Book Holiday Travel Like a Pro

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Nov 18, 2019

We're bringing you tips and tricks to Celebrate Smarter this holiday season. Check it out.

The Story

Traveling around the holidays can be a real ho-ho-hot mess. Between being (approximately) one of one million people flying at the same time, the constant texts from family asking about your ETA, and worries about winter weather, there’s… a lot. 

Already panicking. 

Breathe out. Here’s how to have the smoothest trip possible when it’s time to head home.  

For when flight delays are your biggest nightmare...

We live in this airport forever now. 

Here’s a secret: book the 6 AM flight. Hear us out. Studies have shown that early morning flights have significantly fewer delays. Especially around the holidays, the last thing you want is to get stuck at the airport, watching your flight time get pushed back and dreaming of your childhood bedroom. Plus, if you live in a major city, you won’t have to worry about traffic getting to the airport if you leave home at the crack of dawn. So set your alarm now, and thank us later.

For when you want to save a few bucks…

First, download an app that will help you find the most affordable flights – Hopper is a good one. And as a general rule, try to stay away longer. Not only will you benefit from unlimited (free) leftovers, your flights will be cheaper. So if you can swing it, stay a few days past the big holiday, and look for flights on less popular travel days — say, the Monday after Thanksgiving instead of Sunday.  

Oh and PS: if you’re planning to go wheels up and you haven’t booked your travel yet, do it ASAP. There tend to be fewer last-minute deals in December. Tick tock. 

For when you just want to go somewhere warm...

Beach the change you want to see in the world. Use this tool on Kayak to see what you might be able to swing. Just enter the dates you’re interested in and you’ll get a quick overview of what it will cost to fly where. 

And if your passport has been staring at you, begging to be picked up…this might be the time. Flights out of the country are sometimes cheaper than domestic ones this time of year. European vacation, justified. 

For when you’re not a sprinter…

Not the time to test your Olympic abilities. Planes are packed this time of year, so be careful about booking connecting flights without much time in between. 

If you’re not flying direct, look for connecting flights that leave you at least 60 to 90 minutes for a domestic flight, and at least two hours for an international one. 

For when you can’t face the security line…

TSA pre-check is your friend. Or Global Entry. Or Clear. The point is, you have options that don’t include standing barefoot in a long line of other people also standing barefoot. Here they are:

  • TSA pre-check is the simplest and cheapest option. For $85, you get five years of expedited security (translation: a shorter line, shoes on, and your laptop stays in your bag). To qualify, first submit an online application, then schedule an in-person appointment that will include a background check and fingerprinting. After that, the process takes about two or three weeks to complete. 

  • Global Entry is just a little bit pricier: it’s $100 for five years, with the same benefits applied to international travel. This also involves an online application followed by (you guessed it) an in-person interview. After that, expect to get your Global Entry card within two weeks. 

  • Clear will cost you the most by far ($149 for one year), and will get you in a separate security line that lets you through with a fingerprint or eye scan instead of traditional ID.  You can enroll at any Clear location, and they say it only takes five minutes. 

For when you’ve finally made it to the airport…

Home stretch. But there are some things you’ll want easy access to pre- and in-flight. So don’t forget to pack your…

  • Liquids separately. Enter those cute mini bottles. Keep them in a separate bag so that you’re not fumbling through your makeup bag at security. 

  • Charging cord. Airports have outlets galore, but you still need the gear. 

  • Extra scarf or blanket. It tends to be chilly on planes, and there’s nothing worse than shivering through a long flight. 

  • Neck pillow and eye mask. Because you need optimal conditions to catch some zzs.

  • Book (or newspaper. Or knitting). We’re talking about some form of non-electronic entertainment. Good to have on hand in case of terrible in-flight entertainment options. You hate to see it. 


Travel this season doesn’t have to be (quite) as bad as they say. If you’re strategic about booking flights and deliberate about what you bring, you’ll jingle all the way home (or wherever) with your holiday spirit intact. 

PS: If you purchase anything in this article, theSkimm may get something in return. If something’s out of stock, oops, it was there when we published. Thanks.

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