Booking Cheap Flights Made Simple: Your Step-By-Step Guide For 2023

I think the main reason we all hate booking flights is that we never know if we overpaid… 

…and ain’t nobody wanna overpay. It just hurts. 🤕 

Sadly, there is simply no way to guarantee you’re getting the best price…  

…but with the following tips, you’ll be 95% there and can rest easy because it’ll be as close to the cheapest airfare as possible as anyone is getting without fine-tuning their ESP skills. 🔮 

We’re going to break this down into two categories to make it even easier on ya: if you are open to dates, and if you have specific dates picked. 

Let’s start with the open calendar route…  

Open To Dates

booking cheap flights

If have a specific destination but are open to dates, you’ll have a much better chance at cheaper flights. Here are a few options for hacking with this variable:      

  • Check out your “prime booking window” on This will tell you when your best shot is at booking a flight to your destination.       
  • Use Google Flights‘ “date graph” to see a calendar view of prices. We also use their ITA Matrix but Google Flights is more intuitive and lately, we’re finding you can nab better deals with it. Use this in cahoots with the prime booking window to really get the cheapest.     
  • Sign up for Dollar Flight Club and get alerted by email of hugely discounted airfare to your destination. We’re talking 60-90% off! They have a free account, which is slightly more limited, but still worth signing up for.  

Ideally, what you want to do is look yourself for flights while you monitor the alerts that come in. This way you’ll truly have your finger on the pulse of what’s available for your destination. 

Those tools alone can save you hundreds or thousands on your next flights. But what if you have specific dates and a sole destination?

Specific Dates

It becomes a bit more work to find and book cheap flights if you have specific dates, but we’ve got you covered… 

Here’s the formula for you:      

  1. Get a gauge on the best time to book with CheapAir’s “prime booking window” because when you book matters the most (on average this is 2-3 months out for domestic and 3-8 months out for international, but the tool will tell you more).      
  2. Search your dates in Google Flights.      
  3. Search the same dates in Momondo to double check you found the lowest (at least for the time you’re looking).      
  4. Search SkipLagged (who finds loopholes in airline pricing not usually posted elsewhere) as one last check.      
  5. If you don’t like the prices you see, keep track of them while also setting up price drop alerts on Hopper for push and/orAirfarewatchdog for email. Also use Dollar Flight Club because although it won’t monitor your specific route, you still might luck out with a doozie of a deal.      
  6. Once you find a good price you’re happy with, book it, turn off all your flight alerts, and don’t look back!   

This process will ensure you get a pretty damn good deal, so don’t waste your time scouring and scouring to save a few more bucks(and stress yourself out while doing so). KNOW you got a good deal and be happy with it.   

Here are a few additional tips to remember:

  • If you find a flight through a price comparison site, always attempt to book on the airline’s site first because it will save you a LOT of hassle with any changes you may need to make (and you can log some extra points too).      
  • Many flight aggregators don’t include “budget carriers.” So take note of the low-cost carriers in your area and double check their websites before you book elsewhere.      
  • If flying with two or more people, compare the price of a single ticket to that for your party. You’ll often find that it doesn’t shake out and that the single is cheaper. Airlines “group” seats together and often bump the group up a fare level (depending on how many seats were available at the lower fare).  

That takes care of booking flights on the cheap! I hope this serves you well in booking cheaper airfare so you can jump on a plane more often! 

Onwards and upwards, amigo! ✈️

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