How to Find Cheap Flights When Dates are Flexible

We’ve all been there, haven’t we? You’re planning that dream vacation, daydreaming of exotic places, only to be rudely awakened by exorbitant flight prices that could fund a small kingdom.

But hold on my dear co-hort. If you’re not bound by pesky things like specific travel dates, you’re already ahead of the game.

Yes, knowing how to find cheap flights when dates are flexible is like having a golden ticket in the travel world. Some may say it’s all luck, but it’s not. Buckle your bib…eh, seatbelt, because here are some top tips and strategies to snag the best deal on those sometimes elusive airfares.

How to Find Cheap Flights When Dates are Flexible

Be Flexible on Departure and Arrival Cities (If Possible)

Ah, flexibility – not just a useful trait for yoga enthusiasts. If you can be flexible with your departure and arrival cities, you’re one step closer to bagging that dreamy airfare deal. Here’s how to work this little bit of travel magic:

1. Opt for Alternate Airports

Many major cities have more than one airport. Flying into or out of an alternate airport can sometimes mean significant savings. For instance, instead of flying into LAX in Los Angeles, consider Burbank or Long Beach. In New York? JFK might be the crowd-pleaser, but don’t snub LaGuardia or Newark. Your wallet will thank you.

2. Consider Nearby Cities

Sometimes, you find the cheapest savings aren’t even in your desired city. Plot twist, right? If you’re aiming for San Francisco, flights to San Jose or Oakland might be cheaper, and they’re both just a short drive or train ride away. You get to see an extra city, and you save money. It’s like buying one shirt and getting a second one at half price. Score!

Use Google Flights

Alright, put down that crystal ball. You don’t need psychic abilities to find cheap flights; you just need Google Flights. The future of cheap flight- booking is already here, folks.

1. The Price Graph Feature

Why guess when Google Flights can literally show you when it’s the cheapest flight to fly? The Price Graph feature gives you a visual of prices over a range of dates. It’s like having X-ray vision, but for flight prices.

2. Explore Destinations

For those times when wanderlust hits and you think, “I just want to go somewhere… but where?” Google Flights has your back. Their “Explore” feature lets you input your home city and see prices for the cheapest flights to various destinations. You might discover an affordable gem you hadn’t even considered.

3. Price Tracking

Are you the sort who sets ten alarms in the morning? Then you’ll appreciate this: Google Flights can notify you when prices drop for a return flight on your desired route. It’s like having a personal butler who taps you on the shoulder saying, “Pardon me, but your cheaper flight is ready.”

4. Mix and Match Airlines

Don’t be loyal to just one airline. It’s not a relationship; it’s business. Google Flights allows you to see combo options, which means departing on one airline and returning on another. It’s the mixtape of flight bookings.

Speaking of Google Flights, Check Out These Engines & OTA’s:

While Google Flights might be the dazzling starlet of the flight search party, it’s not the only one on the red carpet. There are a bevy of other options out there, each with its own set of features that are almost as irresistible as a plate of freshly baked cookies. Let’s take a look at the competition:

Skyscanner (Use the Flexible Dates Feature)

Now, if Google Flights is the diligent student in the front row, Skyscanner is its laid-back, yet equally intelligent counterpart chilling in the back. Its flexible dates feature lets you see prices for a range of dates, much like that aforementioned starlet. Oh, and its “Everywhere” search? It’s like the mystery flavor lollipop of flight searches – you’re not sure where you’ll end up, but the journey’s sure to be sweet.


Momondo is like that friend who has the inside scoop on all the best deals and isn’t afraid to share. Its colorful interface isn’t just pretty; it’s also incredibly functional, offering multi-city searches and even a nifty flight insights feature that gives advice on the best days to fly. Who knew a search engine could also be a travel guru?

Kiwi? No, we’re not talking about the fruit or the bird here. is a gem for those willing to be a bit adventurous. Its specialty? Piecing together different airlines for the cheapest possible journey. The result? Occasionally quirky layovers and a truly unique itinerary. It’s like making a pizza with both classic and unexpected toppings. A bit of a wild choice, but oh so satisfying.

Kayak (Can be good… sometimes)

Kayak is the classic hit that’s been on the charts for years. Sometimes it’s the top song, other times it’s overshadowed by newer tunes. While it’s known for its comprehensive searches, be sure to cross-check with other platforms, as sometimes the deals might not be as hot as they seem. Remember, even the best of us have our off days.

Timing Is Everything, Except When It's Not: Finding Flights a Week Before and After Your Ideal Date

Let’s face it: in an ideal world, we’d all plan our vacations six months in advance, nailing down the best deals with the precision of a surgeon. But back here in the real world? Life happens. Maybe you were waiting for your paycheck, perhaps a spontaneous whim took hold, or you just plain forgot. (Don’t worry, we won’t judge too harshly.) The point is, sometimes you’re trying to find that magical fare just a smidge off your perfect date. Well, dear traveler, here’s how to turn that near-miss into a near-hitch.

1. The Magical World of +/- 3 Days

Most booking engines, like the high and mighty Google Flights, Skyscanner, and even the sometimes underwhelming Kayak, offer a +/- 3 days (or similar) feature. It’s like browsing through alternate realities where your vacation started on a Tuesday instead of a Saturday. Engage this feature, and marvel as price options cascade like a waterfall of savings.

2. Fare Alerts: Your New Best Friend

If you haven’t already set up fare alerts, what have you been doing? Seriously. Platforms like Skyscanner and Google Flights allow you to track prices for specific routes. Should a cheaper option pop up a week around your desired date, you’ll be the first to know. It’s akin to having an insider at a private auction. Sure, everyone else will find out eventually, but by then you’ll already be sipping that in-flight mimosa.

3. Flexible Destinations: Go Where the Deal Is

While we’re talking flexibility, don’t just stop at dates. If you’re open to various destinations (and why wouldn’t you be, you adventurous soul?), keep an eye on deal newsletters like Scott’s Cheap Flights or The Flight Deal. Sometimes, the week before or after your ideal date, another destination entirely has a deal so sweet it’d be a crime to pass up. It’s the travel equivalent of going to the store for bread and leaving with a discounted gourmet cake.

4. Forget Round Trips; Embrace One-Ways

It might seem counterintuitive, but booking two one-way tickets can occasionally lead to better deals than a round trip, especially if you’re dancing around specific dates. Different airlines might have offers on different days, and this method allows you to cherry-pick the best of both worlds. It’s like choosing both chocolate AND vanilla when everyone else sticks to plain old swirl.

5. Cast a Wide (Flight) Net

Remember that bit about checking multiple search engines? It’s not just clever advice; it’s downright essential when you’re this close to the wire. Different platforms have varied deals with airlines and may display different fares. So yes, cross-referencing search results is a chore, but one that could save you big bucks.

Finding the Best Airfares for a Given Month: Because Who Needs a Specific Date Anyway?

Alright, you savvy wanderluster, so you’ve got a month in mind but no particular date pinned down? That’s like walking into an all-you-can-eat buffet and wanting a bit of everything. Luckily, the airfare buffet can be just as delectable (and potentially less calorie-laden). Let’s dive into the smorgasbord of options available to find the best fare for your flexible month of choice.

1. Month-View Calendar: Your Visual Aid

Many booking platforms offer a month-view calendar, displaying the lowest prices for each day. It’s like seeing the entire chessboard before making your move. Google Flights and Skyscanner, for instance, let you set your month, then visually feast on the fluctuating prices. So, if you’re a visual learner, these sites might just be your ticket to savings.

2. Fare Prediction and Historical Data

Platforms like Hopper and Kayak (yes, we’re giving them another shout-out) use historical data to predict future prices. They can guide you on whether to book now or wait for a potentially better deal in your chosen month. It’s like a financial advisor for your travel plans. So, why dive blindly into the future when you can take a sneak peek?

3. Use the “Cheapest Month” Feature

Some booking engines, like Skyscanner, offer a “Cheapest Month” option. If you have a rough idea of when you’d like to travel but can shift it for the right price and flexible date, this feature is a godsend. It’s like finding a golden ticket in your chocolate bar – a pleasant surprise that could save you a pretty penny.

4. Beware of Peak Seasons and Special Events

Knowledge is power, folks. Before setting your sights on a month, it’s wise to check for any major events, festivals, or peak seasons. Sure, Carnival in Rio sounds fun, but if you’re budget-conscious, prices might skyrocket. It’s like trying to buy roses on Valentine’s Day. Be smart and adjust your dates accordingly.

5. Join Fare Alert Newsletters

Apart from platform-specific alerts, join newsletters like Scott’s Cheap Flights or Airfarewatchdog that send hot deals for wide date ranges. They’re like those coupons you get in the mail, but for something you actually want. When an irresistible deal for your desired month lands in your inbox, you’ll be poised and ready to pounce.

Using Skiplagged: It's Like Finding a Secret Door, But Airlines Want It Locked

Alright, savvy traveler, we’re about to venture into slightly murkier waters. The kind where you find treasure but have to watch out for pirates. Enter Skiplagged – a platform so sneaky in its approach to finding cheap flights, it has airlines clutching their pearls and gasping in horror.

1. What’s the Big Deal?

For the uninitiated, Skiplagged specializes in “hidden city” ticketing. This is where you book a flight to a less popular destination with a layover in your actual desired city, and then simply disembark during the layover. Sneaky, right? It’s like buying a ticket to a concert but leaving after seeing your favorite opening act because you weren’t really there for the main show.

2. Why Airlines Aren’t Sending Skiplagged Love Letters

Airlines set prices based on demand, not distance. That’s why a direct flight to a popular city might be pricier than one with a layover there. Skiplagged capitalizes on this quirk, but airlines see it as a violation of their fare rules. It’s the equivalent of finding out someone’s exploiting a loophole in a game you created. Can you hear the distant sound of lawyers rubbing their hands in glee?

3. The Legal Tangle

A few airlines have taken legal action against Skiplagged. While these attempts haven’t been particularly fruitful, it’s a stark reminder that this method is frowned upon. It’s a bit like sneaking into the VIP section of a club; just because you haven’t been caught doesn’t mean the bouncers are okay with it.

4. Risks and Tips for the Bold Traveler

If you’re thinking of dabbling in the “hidden city” arts, remember:

  • Never Check-In Luggage: It will go to the final destination on your ticket. So unless you’re planning a surprise visit to a random city, carry-on only.

  • Use Sparingly: Airlines might not notice one skipped leg. But if it becomes a habit? You risk losing frequent flier points or even getting banned. It’s like stealing cookies from the jar; once might go unnoticed, but do it often, and there’ll be consequences.

  • One-way Tickets: If you miss one leg of a round-trip journey, airlines usually cancel the rest of your itinerary. So, for this trick, it’s one-way tickets or the highway.

So, while Skiplagged offers a tantalizing option for scoring great deals, it’s essential to tread with caution. Remember, in the grand game of airfare chess, it’s always good to be a few moves ahead, but never at the cost of getting checkmated.

To Conclude This Flexy Party…

We’ve danced through the quirks of flight bookings, side-stepped some airline pitfalls, and winked at a few sneaky tricks along the way. From the classic moves of Google Flights to the daring cha-cha of Skiplagged, you’re now armed with a toolkit of strategies that even the savviest globetrotters would envy.

Remember, the travel world is your oyster (even if airlines sometimes act like the grumpy oyster farmers). With a touch of flexibility and a sprinkle of cunning, the world’s best deals are yours for the taking. Go forth and conquer those skies!


1. Is there really a big difference between various flight search engines? Absolutely! Each flight search engine has its partnerships, quirks, and special algorithms. It’s like comparing shopping at Walmart to browsing Amazon. They might have overlapping deals, but each offers unique finds. The more you check, the better your chances.

2. What’s the deal with Skiplagged and hidden city ticketing? Skiplagged capitalizes on the “hidden city” method – booking a ticket with your destination as a layover and skipping the departure city until the last leg. While it’s sneaky and often cheaper, airlines aren’t fans, and there can be repercussions. Use at your own risk!

3. I’ve heard of fare alerts, but do they really help? Would we lie to you? Fare alerts are like having a personal shopping assistant who only buzzes when they spot a killer deal. Perfect for those with a touch of laziness or just really busy lives.

4. Can airlines really take action against me for using tricks like Skiplagged? In theory, yes. They can revoke frequent flier miles or even ban you. It’s a rare occurrence, but remember: every time you play the game, you’re rolling the dice.

5. How reliable are month-view calendars for flight prices? Pretty reliable, actually. They give a broad view of flight price trends for the month, helping you pinpoint cheaper days. Still, as with everything in life and online travel agencies, it’s always a good idea to double-check.

6. Why are peak seasons and special events a big deal when booking flights? Supply, meet demand. Peak seasons and major events drive up demand, making prices soar. Always research flight times to your chosen destination to avoid getting caught in a tourist price trap.

7. Why would I book two one-way tickets instead of a round trip? Sometimes, different airlines offer deals on different days. By booking two one-way tickets, you could potentially snag two deals. It’s like getting the best toppings from two different pizza places for the lowest price for one epic meal.


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