Categories: Tips & Tricks

How to Play Flight Roulette and Travel Cheap!

Trust me when I say…if there’s one person who can find cheap flights, it’s me. In fact, the reason why I was able to travel to so many countries was because of a little game I made up called Flight Roulette.

Essentially what I do is type in “Everywhere” as my destination, and “Entire Month” as my date, then marvel at the search results. Listed in order from cheapest to most expensive are all the countries I can go to, and I simply pick the cheapest ones I haven’t gone to yet!

This works best if you have an extended period of time to hop around countries, but it can also save you money booking flights to one destination. Essentially, you create your own layover. It’s sometimes not as convenient, but if you’re more into saving money, you’ll appreciate it!

 Here’s How to Play Flight Roulette

  1. I usually use Skyscanner but any cheap-fare-finder site with a flexible destination and date tool will work. Open a NEW window (ideally clear cookies and whatnot) and head there first.
  2. Type in your current location as the departure city (unless you’re looking up a future trip from somewhere else)
  3. THEN! Instead of typing in a destination, click on the box for destination and choose the option that says “EVERYWHERE”.
  4. IF you can do flexible dates, it will really help! To see the pricing of different dates, tap on the date-box and click “Whole Month”. Or if you’re really flexible and really want to save the most, you can also click “Cheapest Month”.
  5. Hit search, and voila! You will find the cheapest destinations to fly to from where you entered, and also the cheapest dates to fly!

Check out the tutorial I did below on Snapchat a while ago showing how I booked flights to 4 countries for about $400!

Free flight comparison with Skyscanner, your flight search starts here! 

Alyssa Ramos
Alyssa Ramos of @MyLifesATravelMovie is one of the original Solo Female Travel Blogger/influencers for 11+ years! She's been to 140+ Countries, all 7 Continents, 7 World Wonders, 7 Wonders of Nature, and has climbed Mt. Kilimanjaro and Everest Basecamp! Alyssa is also the original creator of Influencer-Hosted Group Trips, and hosts 4-5 adventures per year to unique, remote, and stereotypical "dangerous" places. Tap the Group Trips tab to learn more! After being fully nomadic for 8 years, she now owns an apartment in Tulum and lives part time in Italy with her fiance.
Alyssa Ramos

Alyssa Ramos of @MyLifesATravelMovie is one of the original Solo Female Travel Blogger/influencers for 11+ years! She's been to 140+ Countries, all 7 Continents, 7 World Wonders, 7 Wonders of Nature, and has climbed Mt. Kilimanjaro and Everest Basecamp! Alyssa is also the original creator of Influencer-Hosted Group Trips, and hosts 4-5 adventures per year to unique, remote, and stereotypical "dangerous" places. Tap the Group Trips tab to learn more! After being fully nomadic for 8 years, she now owns an apartment in Tulum and lives part time in Italy with her fiance.

View Comments

  • Alyssa, this does work but I think that it is more about being flexible with destination and/or date of travel. I do think it is a brilliant travel hack however.

    • Yeah that's kind of the point lol, I have another tutorial that's exactly that, I call it using the "flexible option", I'm actually working with Skyscanner next week in Indonesia to promote it! ;)

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