How to Get Cheap flights: Flexible Dates and Destination

If you love cheap flights (I mean, who doesn’t?) then this guide is for you. I’m going to show you how I find the best fares when I’m flexible on both my dates and destination.

If that’s not right for your situation, the following guides will be coming very soon.

  • Cheap flights | Specific destination and dates
  • Cheap flights | Specific destination and flexible date
  • Cheap flights | Specific dates and flexible destination
  • Cheap flights | Alternative travel hacks
Chelsea Holiday Scams to Avoid

Before We Book Our Cheap Flights

There are some helpful things to bear in mind before we begin booking our cheap flights:

  •  Do your searches in private browsing mode
    Some search engines say they don’t use your browsing data in this way and others even question the effectiveness of this approach, but it sure doesn’t hurt to keep your search history private so there’s no chance anyone can bump up their prices based on your previous activity

  • Book your flights on the ‘best day’
    Now, this is very subjective and whilst there’s been many studies on ‘the right time to book’, the data is always changing. In general I would just try to avoid booking at a time when there’s been a surge in interest – i.e. if a big festival or sporting event has just been announced at a location, or a mainstream TV show has just shown a programme about a destination, these factors are likely to bump up prices at that moment

  • Book your flights 5-8 weeks in advance
    In general the numbers say that booking too far out and too close  can mean forking out more. My biggest tip here is that if you need to book a flight in the next week or so, just get it booked. It’s unlikely it’s getting cheaper and also the reason why nobody turns up at the airport on the day of to catch a last minute deal any more. It doesn’t work that way!
money, card, business
  • If spending over £100, buy on a credit card
    If you’re spending over £100 you’ll get an extra level of protection thanks to Section 75 of the Consumer Credit Act which basically says that if you don’t get what you paid for, your credit card company can help you get the cost back – it’s come in very handy to those who have recently been after refund from travel affected by COVID-19
  • If spending under £100 or paying on a debit card, be aware of your chargeback rights
    Whilst less of a protection than Section 75, chargeback allows you to ask for your money back if you don’t get what you pay for and the purchase was made in the last 120 days. Payment companies like Paypal can also protected your rights too.
  •  Get insurance once you’ve booked rather than waiting until you travel
    Once your holiday is booked you want to be covered straightaway rather than leaving it until your travel dates. This is so if anything goes awry that impacts your ability to travel, you’ll be covered. The good news is that there’s even COVID-19 travel insurance now!
My top tips on how to get a free flight upgrade to Business Class including over 50 real life examples of those who were successful.

How to Book Cheap Flights When You're Flexible on Dates and Destination

Being this flexible can be a blessing and a curse. You may be able to jump on whatever deal you see but it does mean your options are endless.

In fact, if you really want to help filter through the results, you may find selecting 5 destinations and then following my guide to booking when you know your destination and not your dates may help.

But if not, here’s a few of the ways I look for cheap holiday inspiration when I’ve got the option to go anywhere at any time.


  1. Head to Skyscanner
  2. Fill in your departure airport
    You can click ‘add nearby airports’ or even type in ‘United Kingdom’ if you really want to open your options up
  3. Type ‘Everywhere’ as your destination
  4. Select your dates
    Click on the box below ‘Depart’ and select ‘Whole Month’. You can then either opt for a Whole month, such as ‘June 2021’ or simply select Cheapest month


  1. Head to Google Flights
  2. Fill in your departure airport
  3. Leave the destination blank 
  4. Select any dates
    You will be able to change this afterwards but at this stage it’s just important to get to the next page
  5. Click ‘Search’
    You’ll then see the next page which shows you a map view and gives you so many more options to play with
  1. Click on your departure date and selectFlexible dates’
  2. Select ‘all’ or what month you’d like to travel and click ‘Done’ You can also opt to search for trips just across the weekend, or that are one or two weeks long here
  3. Search the map for destinations You can use the price, stops, airlines, bags and duration options to filter down your choices too – and don’t forget you can zoom in and out on the map to see more or less options


  1. Head to Kayak
  2. Fill in your departure airport
    Click on the plus sign to add in multiple airports or select add nearby airports
  3. Leave the destination blank 
    Kayak will then prompt you to select the Explore option
  4. Click ‘Anywhere’
    Here you can select a continent to search if that helps you filter your results
  5. Click ‘Any time, Any duration’
    This allows you to filter your search by a month and by an amount of days
  6. Explore the map
    Similar to Google Flights, you can zoom in and out of the map or drag the map to the area you’d like to explore


  1. Head to Momondo
  2. Fill in your departure airport
    Click on the plus sign to add in multiple airports or select add nearby airports
  3. Leave the destination blank 
    Momondo will then prompt you to select ‘Anywhere’
  4. Click ‘Anywhere’
    You can also select a continent to search if that helps you filter your results
  5. Select your dates
    There’s slightly less flexibility here but you can click on ‘exact’ and select up to + 3 days. You can also search for the weekend trips, Thurs – Sun, where it will search with a flexibility of 4 weeks for you


  1. Head to Ryanair
  2. Fill in your departure airport
    You can’t select multiple here so you will have to do each airport individually
  3. Leave as ‘Anywhere’
    Otherwise you’ll need to note your exact destination
  4. Click on ‘Budget’ 
    Select the amount you want or type it in
  5. Click on ‘Let’s go’
  6. Click on ‘Fly out’
    You can select Entire month or Next 3 months here but my favourite is Date range which allows you to select several days which you could leave on, and the same for coming back


Another option is to look into online groups that specialise in cheap flights.

  • Secret Flying
    Their website and Facebook page regularly post cheap fares but it’s up to you to do the work to find the ones that apply to you! The website does allow you to specify your departure airport so if you want to stick to free tools, I’d start there.
  • Jack’s Flight Club
    Free email updates about great UK deals or you can select to pay £39 a year to access all deals as part of their premium membership
  •  Faredrop
    Similar to Jack’s Flight Club, you can pay £39 a year to get tailored deals sent straight to your inbox

One last important tip

No matter what website I use to find the journey, I always check the prices across: 

It doesn’t make sense, I know, but so often they all throw up different prices so it’s worth checking every single time

Whether you know your dates and destination or just your budget, here's my guide on how to book cheap flights for every occasion.

Did That Help?

I really hope so – I absolutely love hearing about people saving money on their holidays!!

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