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How I Plan Travel: Your Step-By-Step Guide

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Fun fact: One of my favorite things to do is book travel.

Of course, I also enjoy the traveling part, but I really do get as much joy out of the planning process as I do actually going on a trip. I know that's weird, but it's good news for you. Because below, I'm sharing how to score the best deal on the most expensive part of your trip: your flights. 

So the next time you feel like your entire Instagram feed is full of bloggers and frenemies off on fabulous trips abroad (just me?), remember -- that could be you! ;)


Step 1: Tracking

Once I know I've got a trip coming up -- or, more likely, if I want to get a sense as to whether or not I can afford a trip -- the first thing I'll do is go to Google Flights and set up a tracking alert. Input your destination and dates, and you'll get a list of options. Once you've sorted for nonstop flights or applied any other filters you like, you'll see "track prices" appear above your flight options. Toggle that on -- or, if you see one specific flight you want, click into that and then select "track prices" for that flight only. You'll get email alerts if the price of the any of the flights you're watching changes, and you can go back to Google Flights at any time to see a graph of prices over time.

After a few weeks, I'll have a sense as to how much a flight "should" cost based on the average of the fluctuations. (This sounds WAY more complicated than it actually is, I promise. It just gives me more confidence when I go to buy my flights that I'm not getting ripped off.) 

Step 2: Dollars vs. Points

I assume that, if you're reading this, you probably already have a credit card that earns you points for travel. If you don't, this guide to the best travel rewards cards from the Points Guy will point you in the right direction (there are some great offers available right now!).

Here's how I normally solve this dilemma. Since I'm already tracking my flights, I have a general sense as to what they'll cost me if I pay in dollars. If that feels like a good deal (e.g. cross-country flights for under $350), I'll pay for my ticket. But if it's anything short of a good deal, I'll check the value on points or miles.

Depending on your credit card rewards program, you'll be able to transfer points to different airline programs. So let's say, for example, that I want to go to London, and the flights from San Francisco are about $1200. That feels too expensive to me. So I'll take a look at the flights I'm interested in on Google Flights, and I can see there are both British Airways and Virgin Atlantic flights that I'd be happy taking. Then I'll go back to Chase Sapphire (my credit card program), check to see if I'm able to transfer points to either of those airlines, and then go to those airlines' websites to see if they have any award tickets available. In this case, I see British Airways has a roundtrip award ticket available, so I'd call BA to hold the ticket for me (and double check it's available), then transfer my Chase points to BA and book.

A few pro tips here:
  • I never transfer credit card points to an airline until I've called to make sure the award ticket is available. Once you transfer those points, you can't transfer them back, so it's worth double-checking.
  • In order to search for award tickets on any given airline, you'll typically need to make an account. Don't let that deter you -- it takes 30 seconds!
  • Whenever possible, I try to save my credit card points for international travel, as I tend to find the best deals there (in fact, I've found some of the best value award tickets in business class!). 
  • Make sure to look up the value of your credit card points as to transfer them to airline partners to ensure you're at least getting a 1:1 value.

Step 3: Pulling the Trigger

So, when's the right time to actually book your flight? 

Skyscanner just released an analysis of flight booking data from the past two years, and according to their research, it's best to book domestic flights 2-3 weeks in advance, and international flights two months in advance. As a planner, this goes against every fiber in my body. In an ideal world, I'll book international or long-haul domestic flights 4-6 months in advance, and domestic flights three months in advance.

I also typically book flights on Tuesdays because that used to be the cheapest day on average, but according to this new data from Skyscanner, Sunday is actually the best day to book. As for timing, they claim 5:00am gets you the most potential savings, but come on. So not worth it. I would avoid booking flights in the evening, though -- the idea is to book when supply is high and demand is low. But again, your tracking will give you a much better sense as to when you're getting the best deal. The only time I stray from these rules is when booking with points -- when I find a good deal on points, I snag it immediately.

Lastly, for you last-minute, spontaneous travelers out there (please, someone tell me what that's like), there's Scott's Cheap Flights, which started off as a side project of a daily newsletter and developed a cult following in the past year or so. Scott catches mistake fares or flash sales and blasts them out to subscribers so they can get in on the deal before it's too late. Though I've never actually purchased one of his recommendations, it's just fun to know I could!


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