• Jeff @ i-Global Travel

Basic Tools to Book Air if You Have Flexible Dates

If you have flexible travel dates, you’ll have a much easier time finding less expensive flights. Searching for flights only on specific travel dates leaves little wiggle room to find the best prices for on your next trip; sometimes it only requires shuffling your travel dates by a few days. There is no magic day to buy airfare, but there are certain times of the year and days of the week when it’s usually cheaper to fly. It is usually cheapest to fly on Tuesdays and Wednesdays and in the shoulder seasons - late January to early March; May to early June; September to mid-November; and early December (however, cheap flights can pop-up at any time). The internet has some great tools that will search multiple travel dates at once so you can always find out when (and where) it’s cheapest to fly. Here are some of our favorite tools for finding the cheapest flights.

How to Use Google Flights

Google Flights is one of best overall flexible date search tools. Just enter a departure city, arrival city, and any desired travel dates. You will see a list of flights for those travel dates along with many other search filters where you can fine-tune your search by the number of stops, airlines, price range, flight times, connecting airports, flight duration, and even add any potential bag fees. You can enter up to 7 airports in both the departure or arrival fields to search for flights from or to multiple different cities at once. Just separate each airport with a comma after typing in the airport code to add multiple airports. Adjust the filters as you wish and then click on the calendar icon in the “departure date” field to see two months of pricing at once. Unfortunately, you can’t choose a range for the trip length and Google will only search for a specific trip length at one time. It may help to search one-way flights in each direction first and then combine cheap dates in a roundtrip search since not all airlines sell one-way tickets for half the roundtrip price. If your dates are set but you’re flexible on where you want to travel, Google’s explore feature is an excellent tool to just browse where there are cheap flights on the map. Just enter your departure city and travel dates - leave the arrival city blank or just type in a general region such as “Europe” or “South America”. It will then give you a map view with prices all over the globe. You can zoom in/out and scroll around the world to find where it is cheap to fly on those dates. If you enter a departure city and choose the “flexible dates” button when choosing dates it will give you the option to choose any month in the next six months or all months. While Google is a great flexible date search tool, it’s not perfect (it doesn’t show pricing on all airlines - most notably Southwest and often misses other airlines such as Aeromexico and Turkish Airlines).

How to Use Kayak to Find Cheap Flights

Kayak is a good for those who want to search for a flight with a range of trip lengths. You may be willing to stay an extra day or two or leave a day earlier in order to find the best deal. Enter your departure and arrival cities (you can insert up to 3 in each). When choosing your dates, you’ll see color-coded approximate pricing on the calendar, but for a better flex search choose either “Weekend” or “Month” from the left-hand column. The weekend search allows you search for cheap flights departing Thursday, Friday, or Saturday, returning Sunday or Monday, over a 4-week period. The month search allows you to choose a start date for the search and your desired trip duration. You can make this a set number or a range of up to 7 nights. For example, you can choose a trip length of 7 nights, 6-8 nights, 4-11 nights, or 26-33 nights, but not 10-20 nights. It will then search flights for 4 weeks from the start date and gives you the results in a calendar view. It’s always a good idea to click on the “find more options for the same dates” link in the bottom left of this pop-up. This will show you more flight options—some of which may even be a lower price. Kayak is great at finding prices from many different Online Travel Agencies (OTAs), which means it may unearth cheaper flights than Google. It does not include all airlines and routings. Kayak has an explore tool similar to Google. Enter a departure city and leave the arrival blank by clicking on the “Can’t decide where to go?” text. This gives you some great flexibility by being able to choose any month up to a year out or “anytime” to search for cheap flights to anywhere throughout the year. It also has a holiday search tool where you can search for cheap flights during specific holiday periods.

How to Use Skyscanner to Find Cheap Flights

Skyscanner is one of the most popular search engines worldwide. It was one of the first to adopt low-cost carriers in its search results and it continues to provide a very clean and straightforward search for travelers with flexible travel plans. Click on the “whole month” tab when choosing dates, this will allow you to choose any specific month or just choose the cheapest month. A calendar will then appear allowing you to see the best prices for both the outbound and inbound flight at the same time. These results may not be entirely accurate since the price for the return date may depend on the departure date, but it’s a great way to get an idea of when cheap flights may be offered. Once you’ve chosen dates, it will bring you to the list of flights where you can filter your search further to weed out any airlines, trip durations, or the number of stops as you wish. Unfortunately, it’s not possible to filter out airlines or certain schedules before doing a flex search. The only filter possible before you conduct your search is to choose nonstop flights only. This means you can’t weed out any low-cost airlines until you are on the specific dates landing page. Skyscanner includes different OTAs that sometimes have lower fares than what you’ll find on Kayak. The lack of filters available before you conduct a search, however, means it’s often easier to find exactly what you’re looking for with a flex search on Google or Kayak first, and then checking Skyscanner to see if there is better pricing.

How to Use CheapAir to Find Cheap Flights

CheapAir is an online travel agency (OTA) with a unique way to search for cheap flights. From the home page, choose the flexible dates tab and then enter your from and to cities. The flex search tool will only work for certain domestic U.S. markets. It will work for the more popular routes and from smaller markets to major cities, but you may get an error if you try to search from small market to small market. You’ll see a list of fares to choose from; it will tell you the airline and whether or not it is a Basic Economy fare from the start. You’ll also get some brief details on the fare explaining what months it’s available, days of the week it’s offered, and how far in advance of travel you need to purchase. Choose a fare that you want to check for availability and it will bring you to a calendar indicating which days that fare is available and also other dates where you’d have to pay more to fly. Choose dates with the airplane logo to get the price you’re looking for and then choose specific flights. Sometimes many of the fares are only available on very limited dates, but you may be able to unearth fares you didn’t know existed by only searching other sites. The major downside to CheapAir is that it includes a booking fee in the fare you see, which means you can almost always find the same flights for a slightly cheaper price on the airline’s website or another booking engine. However, there are times when CheapAir may still have inventory of a low fare that other sites don’t have or allow for combinations of airlines you won’t find on other booking engines. CheapAir also offers a Price Drop Payback that will give you a credit up to $100 per ticket if the price drops on the same itinerary any time before your trip. This is a nice perk, which may make it worthwhile to pay the small booking fee and book with CheapAir.

How to Use Orbitz to Find Cheap Flights

To search on Orbitz, make sure you have the “Flights” tab highlighted since Orbitz will often default to a “Packages” search. Then, all you have to do is enter your cities, dates, and select the “My dates are flexible” checkbox. If you click on the advanced options, you can choose nonstop or refundable flights, preferred airline, and preferred class. On the next page, you’ll see a matrix grid of prices for travel dates +/- 3 days from what you chose. The lowest fares will be highlighted in green. On the left-hand side of the page, you can filter by number of stops, airlines, departure/arrival times, and nearby airports. Adjusting the filters will not adjust the prices shown in the matrix grid - only the results shown for the exact dates that are chosen. One nice feature of Orbitz is its flight score. It gives each particular flight a score between 1-10 taking into account the airline, flight time, aircraft, and fare. It gets these scores from Routehappy, which is a service that many booking sites use to rate flights. Orbitz also clearly displays baggage fees and other important info by clicking on the “Details & baggage fees” dropdown just under the flight rating. On the "Review your trip" page, you’ll be given options to choose a different type of fare, such as upgrading from Basic Economy to Main Cabin, if available. Orbitz will also clearly state if a fare is eligible for free cancellation within 24 hours at the bottom of this page. Orbitz is part of Expedia Group, which also includes Travelocity, Hotwire, Cheaptickets, and Expedia (of course), among other travel sites. You’ll notice these sites all look very similar and you’ll usually see identical pricing across all of these sites, but there are times when prices can vary. Only Orbitz and CheapTickets have the “My dates are flexible” checkbox from the initial search page.

Airline Sites with the Best Flexible Date Search Tools

There are airlines that have great flexible search tools on their own websites. Although you won’t be able to compare other airlines with these searches, you can sometimes find lower fares on an airline’s site than anywhere else. And in some cases—like Southwest—it’s the only place you’ll find those airlines’ fares.


You won’t be able to book Southwest fares anywhere else so it’s always a good idea to check its low fare calendar in addition to other search engines. There is a link right below the arrival box on the home page.


JetBlue has a somewhat hidden flex search tool. You can find a link by clicking on the “Book” header and then choosing “Best Fare Finder”. It will first display just the current month. Click on the “see more months” link to show more.


Delta’s flex search is also hidden from its homepage. Use to start a search in calendar view by clicking on the “flexible dates” check box and selecting the “5 weeks” option before searching. Delta’s flex search has a unique feature that allows you to filter out Basic Economy fares if you wish.


From United’s home page, click on the “Calendar Shop” checkbox before searching. Then, just choose a month and desired trip length and you’ll be brought to a flexible date calendar. Another option is to start your search from the advanced search page and click on the “My dates are flexible” checkbox.

Alaska Airlines

On Alaska’s homepage, click on the “all search options” box just below the “adults” dropdown field. From there, you can click on a “Flexible dates” checkbox to start a search with a calendar view. You can also switch to a calendar view after doing an exact date search by choosing the “calendar” button in the “view by” section on the left-hand side of the page when choosing flights.

Hawaiian Airlines

At the bottom of the search box on, you’ll see a link for a “Price Calendar”. Click this link to see fares in a calendar view. You can also toggle to a bar graph chart if you prefer.


To find a monthly calendar on, you’ll first have to conduct an exact date search. This will default to a one-week flex search. You can toggle to a month view search by clicking “month” at the top of weekly view of fares. Toggle between the months using the arrows on either side of the calendar.


Frontier also requires you to first search for exact dates and then toggle to a “month view” calendar on the top right of the following page. Unfortunately, you can’t exclude Discount Den fares from the calendar view, but you’ll notice that the standard fares are usually only slightly higher than the Discount Den fares you see on the calendar view.


Like the other ultra-low-cost carriers, Allegiant requires you to search for exact dates first. On the following page, you’ll see a “rate calendar” button on the top right of both the departing and returning flight sections. Click these buttons to see fares on a flexible date calendar. Booking a roundtrip flight on Allegiant often gives you a small discount.

Adapted from AirfareWatchdog, May 2019

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