How to Find Cheap Flights: A Practical Flight Booking Checklist
Cheap Flights Checklist
Finding cheap flights can be hit or miss but persistence and flexibility is key to finding the best fares. Follow our checklist for well learned tips and travel hacks to book the most affordable flights.
Where & How to Track Flights
Websites to Track Flights. We always begin tracking flights on Google Flights. The search by map and calendar features make it easy to visually choose a destination and time to go. We also like comparing across travel search engines like Sky Scanner and Hopper. Lastly, search directly on the airline’s websites. Some airlines have better routes and prices that don’t always show up on flight tracking websites.
Track Multiple Destinations. If you’re like us and have a travel bucket list, track flights to multiple destinations around when you’re planning to travel. This also helps us learn what prices are considered low or high to various places during different times of the year. This method works for near term and distant travel dates.
Tracking Ahead. If you plan on traveling in several months from now and want to go somewhere tropical, track flights to various tropical destinations during that time and book the most affordable option.
Tracking Last Minute. The same method works for spontaneous trips. If you’re planning a getaway this weekend, track flights from your nearest airport to any destinations reachable from there. Sometimes you’ll be surprised to find a very affordable last minute flight.
Know The Best Dates & Times to Travel
Have Flexible Dates and Times. Be flexible when searching for flights. Sometimes departing a day earlier or later can mean spending hundreds of dollars less. This is true of the time of day, especially on well traveled routes.
Book the Red Eye Flight. It might not be the most comfortable time of day to travel, especially if you can’t sleep on airplanes, however the prices almost always cost less in the middle of the night than during mornings or afternoons.
Travel on Grim Dates. Flights are almost always cheaper on days like Friday the 13th or September 11th, especially if booking months out.
Travel During the Curb or Off Seasons. The weather might not be “perfect” but that doesn’t mean you won’t enjoy your trip. We’ve often enjoyed smaller crowds, better service and made stronger connections with local culture and other travelers during the off season.
Plan a Season Ahead. Track and book flights months ahead of time, ideally the season before most travelers have even given it any thought. For example, we begin tracking spring break trips around Thanksgiving, summer travels during the holidays before the New Year and fall getaways during the late spring and early summer.
Travel Abroad on Thanksgiving. If you’re traveling from the United States, international flights are frequently more affordable on Thanksgiving while most travelers are flying domestically.
Don’t Wait to Book. If you feel good about a ticket’s price, don’t wait to book it. Chances are the price won’t be available 24 hours later, especially if it seems too good to be true. Most flights, even if non-refundable, are fully refundable within 24 hours if you change your mind of fine a better flight elsewhere. Alternately, some airlines offer the option to “freeze” a price for up to 72 hours for a small fee.
Consider Your Departure & Destination Locations
Check Multiple Airports. Many major hubs have multiple airports. Flights to and from the smaller or lesser desired airport may be the more affordable option. If you’re based in-between multiple regional airports, flights from one vs the other may make all the difference, even if more distant than your nearest airport.
Book One Way Flights. If you plan it right, one way flights with separate airlines are occasionally cheaper than round trip flights with the same airline. This is especially true if traveling between multiple destinations before returning home.
Avoid Skiplagging. Skiplagging is when you book a flight with a layover but stay in the connecting city. Travelers do this when the connecting route costs less than the direct route. While not illegal, airlines often impose hefty fees, cancel remaining legs of the journey or ban passengers from flying with them.
Choosing An Airline
Book the Budget Airline. We’ve all heard of or have our own horror story from booking with a budget airline. Though there’s usually less leg room, higher baggage fees and less flexibility, most flights depart without issue. The biggest risk is an overbooked flight, a risk worth taking for booking at a significantly lesser cost. If unfamiliar with the budget airline, research recent customer experiences on review sites or Reddit.
Be Aware of Baggage Fees. We rarely check a bag however we always verify baggage fees and restrictions. They frequently change between airlines and countries. Before booking, confirm how many bags are included, what the weight and size restrictions are, if they can be carried on or have to be checked. Fees can quickly add up if you’re not paying attention.
Check for Stopover Programs. Several airlines offer free stopovers, discounted stays or city tours when stopping over in their home city or country. Taking advantage of them is a great way to fit in an additional destination in route to your planned destination.
Lottery Upgrades. Some airlines offer a lottery to upgrade flights to a premium seat up to a week before the flight departs. Place a bid, usually a few dollars higher than the recommended bid to win a chance at upgrading for significantly less than the actual cost.
Volunteer if Asked. We’ve earned hundreds of dollars in flight vouchers and Visa cards on multiple occasions by volunteering to take the next flight on overbooked flight. Though not common, it can really pay off if not in a rush.
Earn Points by Traveling
Sign Up for Frequent Flyer Programs. Most airlines have their own frequent flyer or mileage program to earn points towards booking future flights and covering baggage fees. Several airlines are part of the same network or alliance making it easier to consolidate points if booking with different airlines. Though it can take years to accumulate a meaningful amount of points, simply signing up comes with perks. We’ve received free upgrades, been assigned better seats and received refunds or travel credits on otherwise non-refundable flights.
Use Travel Credit Cards. Sign up for a travel credit card to earn points that cover the cost of flights and other travel related expenses. We have multiple travel credit cards but routinely use two over others.
Chase Sapphire Reserve. A premium travel credit card with steep annual fees but generous travel credits. Amongst other perks, it comes with a Priority Pass that offers access to many airport lounges. Any travel related expenses earn 3 points per dollar spent on the card. Over time, it adds up and more than pays itself off.
Capital One Venture. A travel credit card with minimal annual fees and easy ways to build a bank of points. Any travel related expenses earn 2 points per dollar spent on the card. Their daily shopping offers provide generous points multipliers on various purchases including car rentals and booking platforms like Viator, Get Your Guide, Booking and Expedia.
Persistence & Flexibility
If you’ve read this far, you can tell there are many ways to find the most affordable flights. It’s often a combination of methods on our checklist, the most important of which is persistence and flexibility. Being persistent about finding cheap flights and willing to be flexible to book them is often what lands us the best fares.

