How to Score Cheap Flights

How to Score Cheap Flights: 5 Cheap Flight Hacks

If you’re looking for tips on how to score cheap flights, you’ve come to the right place.

We’ve put together this step by step guide to the cheap flight hacks we use to get the best flight deals.

Two people can fly on the same plane and pay completely different flight prices of use a completely different amount of frequent flyer points. Let’s make sure YOU are the one with the best deal!

If you’ve been following our world travel challenge and wondering how we afford to travel as digital nomads, these travel hacks for cheap flights are the answer whether we are buying tickets or using Frequent Flyer miles.

How to Score Cheap Flights with Cheap Flight Hacks

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Our 5 Favorite Cheap Flight Hacks For Great Flight Deals

1. Let the Flight Price Determine Where You Go

When I’m planning a trip, I start with a region in mind instead of looking for flight deals to a specific airport. I try not to have too many parameters. I’m a little flexible with dates and I try to be flexible with cities.

For instance, if I am doing a trip to Vienna, I look at flights into Vienna, Bratislava, Budapest and Prague. They are all close to each other and on my trip I might be wanting to visit all those cities.

Obviously I don’t go where I don’t want to go but sometimes, I see a flight deal to a new destination that seems really exciting after learning more about it.

If a great deal is happening on a certain route, use it to your advantage. For instance, if you are flying from Los Angeles to the south of France, it may be cheaper to fly into a major hub like Paris and catch a cheap Ryanair flight from there to Nice.

Sometimes the cheapest deal involves a stop over of 24 hours where you get an extra day in a cool city.

We put together 17 beautiful cities in France, the best 22 places to visit in Spain and 22 Italy Weekend Breaks for this specific reason.

Score Cheap Flights Barcelona
The cheap flight hack I used for a trip to Santorini Greece was to fly through Barcelona for half the price.

2. Flexible Dates are Key to Cheap Flight Hacks

  • If you are using frequent flyer miles, search as far in advance as possible.
  • When you are paying for flights, sometimes it can be better to get your flight closer to the date. Typically the best time to buy flights is the season before you want to go. If you know you want to travel in fall, watch for the fall fares that airlines run in the end of summer.
  • If you really want to know how to score cheap flights, especially in Europe, take advantage of the budget airlines flights from late night to early morning. You have to be a serious trooper to go for these but they are often crazy good deals. We just paid $9 each for the 1.5 hour flight from Bratislava to Sofia on the 8am flight.
  • Always keep an eye out for advertised specials or mistake fares. If you do happen to find a mistake fare, book it right away. Airlines won’t always honor these but you do have a chance at getting the deal of a lifetime.

3. Use Flight Search Engines to Find the Best Flight Deals

I use Skyscanner and for flights, It’s good to have two options so you can check them against each other.

I also just started using WayAway, which shows a lot of promise for complete trips from flights to hotels to cars. I’ll keep your posted on how to use it best.

For this example, I’ll use to show how I search for flight deals. Skyscanner works in a similar fashion.

The key to finding the cheapest flights is knowing how to do the search. I’ve explained it step by step below.

How to Score Cheap Flights on Kiwi

How to Score Cheap Flights: Searching on

Let’s say you are going to Barcelona and want to visit another city while you’re in Europe and you are open to a few different options as to what the other city will be.

  1. Start your flight search clicking One-way, even if you are going round trip. You can get more information starting your search one way. Then do a one way search for the return.
  2. Choose the amount of people flying and the bags you are taking. In the example above I selected 1 adult and no bags. Usually I search with 2 adults and 2 carry-on bags. It will save you a lot of headache if you include bags at the beginning of the search.
  3. Enter the city where you will be originating travel in the FROM box.
  4. In the TO box, you can put up to 3 search places. You can put a country like Greece, or choose up to 3 specific cities, or pick a region like “Europe” or choose “Anywhere” to see every deal from the home airport.
  5. Choose dates in the DEPARTURE box. You can choose multiple departure dates. In the above example I picked 2 dates. You can also choose a specific month like “September” or you can choose “Anytime.”
  6. Narrow the options by using the pull down menus. Here you can choose things like non-stop. You can also pick a price range, days of the week, whether or not you are open to overnight stopovers, etc….
  7. Display your results by Cheapest or Popularity. On the right of the pull down menus, I choose to display my results by cheapest.
  8. Once the flights pop up, you can again sort by cheapest, best or fastest in the list of flight options. I usually look at best which takes price and convenience into consideration.
  9. Verify that you have the best deal. Once you’ve figured out what exact flight you want, you can then move to another site to make sure you really found the best deal. It only takes a few more minutes to check Skyscanner.

Look for cheap flights on Skyscanner also!

How to Score Cheap Flights Cappadocia
It took a little creativity but we found some amazing deals to spend 7 Days in Turkey

5 Important Things to Consider for Cheap Flight Hacks

1. Don’t forget the extra costs.

Are you paying for checked luggage, seats, or carry on bags? Try to account for the extras so you can factor them into your price decision.

Sometimes the higher priced flight on Southwest Airlines with 2 free checked bags is cheaper than the Basic Economy flight on United Airlines that becomes more expensive when you add a bag.

2. The value of your time.

We all want a good deal but the cheapest deal might not be worth it. If you are going on vacation for 7 days, you don’t want to take a flight that has a ton of stops.

Each time you stop, there is the possibility that a flight will get delayed or cancelled. If it’s a little more expensive for non-stop, think about what that means for you.

Multiple flights can also mean multiple baggage and seat charges, especially on low cost airlines.

3. Be careful with layovers.

If you find a great flight that involves 2 different airlines, make sure you have enough time in between.

If I book flights on multiple carriers, I use directly because they have a guarantee if you miss a flight.

Even with a long layover, flights can still get cancelled and you’ll lose your money if you’re not covered. The worst part is that you have to pay a high price for a last minute flight without insurance.

4. Buy travel insurance.

In the last few years, we have all learned the value of travel insurance. Beyond a world disruption, you need to protect yourself from unforeseen accidents, health issues, and trip interruptions.

We use SafetyWing travel insurance and the plan they refer to as nomad insurance. Policies are available from 5 days to 364 days. If your policy is over 90 days, it even covers you for a return trip to your home country.

Coverage includes medical insurance, chiropractic care, emergency dental, emergency medical and political evacuation, travel delay coverage, lost checked luggage, emergency response, natural disasters and personal liability.

The price varies by age up to 70 years old. High risk sports and pre-existing conditions are not covered.

5. Understand the value of your money and points.

Think about frequent flyer points as a foreign currency. You need to understand the exchange rate that you are getting. Sometimes that exchange rate is good and sometimes, it’s like robbery.

You need to learn how to score cheap flights to be able to evaluate the right frequent flyer deals. Use your points for the best redemptions. One great place to learn more is to sign up for the Daily Drop newsletter.

How to Score Cheap Flights to Bali
Wondering how to score a cheap flight to Bali? We did it by flying in October.

Avoid These Mistakes Using Frequent Flyer Points

I will be covering frequent flyer points in a separate post. In the meantime, I do want to mention some of the biggest frequent flyer point redemption mistakes.

Don’t waste your miles. You don’t want to be a hoarder and never use them but you want your redemptions to be really great.

  1. Not having a frequent flyer account. When you fly or stay in a hotel, make sure you get points. Then try to stay loyal to a brand or a few brands if possible so you can gain status or enough points to redeem.
  2. Be very careful using your points as dollars. Some travel agents will try to get you to use up your travel credit cards points as dollars. It’s usually better to transfer your points to an airline partner unless you find a really cheap airfare. That’s why it’s important to know how to find inexpensive flights before you start using frequent flyer miles.
  3. Only use your points for non-peak awards. Let’s say you want to fly American Airlines from LA to New York and the ticket is $400 round trip. You check the frequent flyer availability and all of the award saver tickets are gone. The anytime awards are between 30k to 65k each way for a coach ticket. You are much better off paying for that ticket and not using miles. On the other hand, if you can get the 12,500K each way saver tickets, it’s worth it.

Finding cheap flights is something you can get really good at if you invest some time learning how to do it. Here are the best travel credit card offers right now.

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  • Reply
    November 8, 2019 at 1:39 am

    This is interesting! I actually tried doing some in the list though I haven’t tried with I’ve also used up my velocity points when my family went to the states. Your post is very helpful, thanks for showing this.

    • Reply
      November 8, 2019 at 2:14 am

      I’ll be doing more posts about how to get points and flight deals!

  • Reply
    Barbie Holmes
    November 3, 2019 at 8:52 pm

    Wow! Thank you for the inside knowledge. I can’t wait for the day we have more flexibility to travel once Big Rich retires!

    • Reply
      November 3, 2019 at 9:40 pm

      Stay posted. This is the first article of many that will share a bunch of tips to get tons of bang for your travel buck.

  • Reply
    Elegant Duchess
    November 1, 2019 at 11:44 am

    Great tips, finding a bargain flight nowadays is next to impossible! xx
    Love xx
    Elegant Duchess

    • Reply
      November 3, 2019 at 3:04 pm

      Bargain flights are readily available if you use these tips to look for them and have some flexibility. I think you would be really surprised at the deals on Fare Drop.

  • Reply
    Yara Mabote
    October 31, 2019 at 8:09 pm

    Loving these tips! Another great point is to book for tuesday flights, tend to be cheaper!

    • Reply
      November 3, 2019 at 3:24 pm

      I agree that looking for flights on Tuesday can be a good idea. That said, all of my latest deals on my last 10 flights have been on Friday, Sunday and Monday (supposedly the most expensive days) so you never know. I think being flexible and open to any day is key.

  • Reply
    October 31, 2019 at 5:47 pm

    Great tips! I’m itching to travel again, hopefully I can score some good deals!

    • Reply
      October 31, 2019 at 7:57 pm

      I always seem to feel like that. Hope you go somewhere fun really soon!

  • Reply
    Julie | This Main Line Life
    October 31, 2019 at 3:59 pm

    These are such great tips. I’m definitely not very savvy when it comes to booking flights or vacations so this is really helpful.

    • Reply
      October 31, 2019 at 7:56 pm

      So glad it’s helpful! If you have any questions, feel free to post here.

  • Reply
    October 31, 2019 at 8:39 am

    Great tips because I love to travel and I adore bargains! Thank you.

  • Reply
    October 31, 2019 at 6:00 am

    Travel insurance is an absolute must indeed. Great tips dear!


    • Reply
      October 31, 2019 at 3:16 pm

      Thank you!

  • Reply
    Barbara Eskowitz
    October 30, 2019 at 4:19 pm

    Thanks for all this great information. I’m going to check out as well as Fare Drop for my upcoming travels. The only catch for me is typically my schedule is not flexible regarding the travel dates.

    • Reply
      October 30, 2019 at 5:27 pm

      Fare Drop has some deals that are 6 months out. You may surprise yourself with a destination that you always wanted to visit but hadn’t made plans yet. Even with set dates, you can still use these tips to get better pricing. I always find my deal on Kiwi and then double check it on Skyscanner or Google.

  • Reply
    October 30, 2019 at 1:24 pm

    I didn’t know about, I have to check it out next time. I find it such a struggle sometimes and so time consuming to find cheap flights or hotels. In the end though it’s worth the hassle, because you are able to save so much money when comparing the prices a bit. Your tips come in so handy!

    xx Simone

    • Reply
      October 30, 2019 at 3:55 pm

      You’ll be surprised how fast you can get info with Kiwi. It saves me so much time when I use the feature that lets me pick multiple locations or anywhere.

  • Reply
    Allie Mackin
    October 29, 2019 at 7:58 pm

    Oh wow, what an informative post. I will have to keep this all in mind if I go to Paris in February.

    Allie of

    • Reply
      October 30, 2019 at 12:18 am

      You might want to try the free trial of Fare Drop to see if a great deal to Paris comes up in the next month.

  • Reply
    October 29, 2019 at 2:48 pm

    These are so useful tips , and loved these pictures, so beautiful.

    • Reply
      October 29, 2019 at 5:06 pm

      Thank you!

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