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Samantha Maloney

How to find cheap flights to anywhere

Updated: Dec 21, 2023

The holidays are upon us! More get-togethers means more traveling to visit friends and family. Here are my top tips to find cheap flights to anywhere for the holiday season and all year round! 

airplane view of Chicago

  • One-way tickets vs round trip tickets

    • Sometimes you can get a little bit of a deal if you book 2 one way tickets rather than booking a roundtrip ticket. It’s not the most common but it’s been known to happen!

  • Mix and match airlines and airports

    • When I fly to Florida I find that that taking spirit is usually the cheapest but you might be able to find a great deal your departure flight and arrival flight are 2 different airlines. Kind of the same idea of 2 one way tickets versus a round trip ticket. I live in Chicago so I can also see if it would be cheaper to fly out of O’hare and back into Midway and vice versa! You can’t always do that with round trip tickets

  • Bundles vs booking flights and accommodations separately

    • One of my favorite travel sites is Expedia. I love it so much that I applied for the Expedia+ Voyager credit card with Citi Bank, which unfortunately is no longer available. Regardless, I think it’s the easiest travel comparison website because you can easily compare flights and hotels rather than having a million pop-ups making you click from window to window to compare prices. You can also get a discount on bundle deals. 

    • For flights alone, I like using Google flights. They list all airlines (except Southwest, I believe) right on their site for you to compare. Just be sure to clear your cookies or go incognito which leads me to my next tip...

  • Clear your browsing history/ search incognito 

    • Let’s back WAY up. Airlines price their flights based on interest. The more interest in a flight or location the price is likely to go up. When you’re constantly searching for flights on Expedia, Google, and especially the airlines website itself the browser saves your search history and cookies then the airline can use this info to price the flight accordingly. On Google Chrome you can start an incognito tab that doesn’t save your search history or cookies.

  • Book your flight WAY in advance

    • Like I mentioned in my last point airline websites price flights based on people’s interest in that flight. If you know you’re going to be traveling for the holidays, either book your flight way in advance before airlines start gauging interest and price accordingly. On the flip side, you could wait to see if you see a better price closer to the departure date but then you MUST purchase it because chances are the price will go up. I love using the hopper app. Personally, I find it to be the most accurate. I went to Dapper Day at Disney World last minute because Hopper told me when to book a flight for  $120 round trip! 

  • Enroll in a frequent flyer program or credit card

    • As I said before I have an Expedia+ Voyager credit card and I (used to) earn points on every purchase PLUS 4x points on Expedia purchases, 2x the points on dining and entertainment and 1x on everything else so naturally I try and use this card for all my purchases and watch the points add up! I find this card is one of the most rewarding because your points are worth double on VIP hotels and on Expedia you can apply points to your purchase whereas with an airline you have to either pay in full with points/miles or pay in cash. Airline credit cards are the hardest to redeem because you usually only get 1x the points on purchases (maybe 2x on airline purchases) but you need 10k - 30k points before you can even redeem them. With the Expedia+ card you also get a $100 annual credit to use for things like in-flight purchases, baggage fees and TSA precheck (which is amazing btw! Let me know if you want me to share my experience with precheck!)

  • Travel Hacking

    • This is when you open new credit cards all the time in order to cash in on the new member rewards like 60k miles when you open an AA credit card or a free night when you open a Marriott card. TBH, I kind of hate this tip BUT it works for some people so I had to include it. I dont like it because if youre frugal like me, trying to pay off your previous credit card debt, or just plain cant be trusted with credit, youre going to be tempted to use it all the time and then all of a sudden you have tons of credit card debt. no thanks. BUT like I said it works for some people so you decide.

Hope this helps you get cheap flights for all your upcoming travels!


Until next time!

xoxo

Sam


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