Cheap Flights

Two itineraries are frequently cheaper than one. Plus you can stay and explore another city for as long or short as you like.

Here's a personal example: I used to live in Washington DC, but the best ticket I ever purchased was the ticket I mention, above, a Mistake Fare from NYC to Milan for $130 roundtrip.

It was well worth the $20 bus ride up, and I even got to spend the weekend with friends in NYC. If I had insisted on flying to Milan from Washington DC (not NYC) the ticket would’ve been around $800, not the $150 I actually paid.

The next best fare I’ve gotten was from DC to Brussels for ~$250 roundtrip. So nice I bought it twice! Even though I didn’t have that much interest in Belgium, I knew once I was in Europe, I could easily find budget flights to other European countries.

For one trip I bought flights from Brussels to Norway (~$60 roundtrip) and for the other trip I bought flights from Brussels to Dublin (~$80 roundtrip). If I had insisted on flying from DC to Norway or Dublin (without stopping first in Brussels), I would have paid around $750 roundtrip, not the $310 and $330 I actually paid. And I wouldn’t have gotten a day in Brussels to boot! Rome2Rio makes it easy to check out local transport options between destinations.

Let’s say you and your partner want to fly from Seattle to Washington DC. At time of writing, the cheapest nonstop flight was $299 per ticket.

But a funny thing happens when you reduce the number of travelers from 2 to 1: the price on the exact same flight drops from $299 per ticket to $199.

This pricing anomaly sometimes occurs because whenever you’re booking multiple tickets, airlines want to put your entire group into a single fare bucket.

(A fare bucket is a fancy term that airlines use to denote not just which cabin you’re in, but also any privileges included with your ticket like whether it’s refundable or if it’s upgrade-eligible. The number of seats available in any given fare bucket isn’t a secret but it takes some digging to find; all we’re typically shown when we search for flights is the lowest ticket price.)

In the above example, Alaska Airlines almost certainly only had one ticket left in the cheapest fare bucket priced at $199. So if you searched for two tickets, the airline would skip over the single $199 ticket and instead only show you fares with at least two seats available, $299 in this case.

But by booking one ticket at a time, you can get the first one for $199 and the second one for $299, paying $498 total rather than the original $598.

Does this work every time? No. But anytime you’re traveling with a group, it’s worth checking if fares are cheaper by buying tickets individually. That’s especially true if you’re traveling with a larger group, because the more tickets you buy, the greater the chance there won’t be enough seats for you all in the cheapest available fare bucket.

If you’re able to successfully use this strategy, call the airline after you book and ask to have the multiple itineraries linked. That way, if there are any changes to your flight, the whole group will be able to stay together.

It will also vary a bit by the specific destination, especially around popular festivals. Fares to Dublin for St. Patrick’s Day or to China for Chinese New Year aren’t cheap.

There's so much bad info out there about the best time to book a flight, with many people claiming it's Tuesdays at 1pm, or early on Sunday mornings. If I achieve one thing in my brief stint on Earth, it will be to convince travelers to stop believing this nonsense. It’s not true, it won’t help you get cheap flights, and if anything will likely result in you overpaying for your next trip.

The better strategy for snagging discounts on flights is to book within what I call the Goldilocks Windows.

Airfare doesn’t change weekly these days. It changes daily, hourly, sometimes even minute-ly. Neither I nor anyone else can tell you with certainty when (or where) next week’s cheapest fares will pop up.

These days, airfare is set by complex algorithms that account for hundreds of ever-shifting factors, from consumer demand to oil prices to competitor’s prices and beyond. One factor airlines no longer rely on: technological constraints that only allowed them to change fares once a week at a set time.

Though there’s no set time or date that’s always cheapest to book, there’s still a period when cheap fares are most likely to pop up. I call these Goldilocks Windows.

Cheap Flights

For domestic flights, the best time to book is normally 1 to 3 months before your travel dates. For international trips, it’s 2 to 8 months prior. If your trip is during a peak travel period (Christmas, summer, St. Patrick’s Day in Dublin) add a couple months to those windows. If you’re traveling during low season it’s more likely cheap fares will pop up closer to departure date, but prices tend to jump in the last month or two before departure, so you don’t want to cut it too close.

You also want to pay attention to times when you know airfare is actually going to go up. At that is at the 21-, 14-, and 7-day marks before departure. Most fares include an advance purchase requirement, which mandates that a particular fare bucket is only available if booked, say, 21 (or 14 or 7) days or more in advance of travel.

Airlines know leisure travelers tend to book flights early and business travelers tend to book flights late. Airlines want to make sure they milk as much money as possible from business travelers who don’t care what the flight costs (it’s their company paying, after all), so they increase fares on the type of tickets business travelers buy, including last-minute bookings.

If you’re hoping for legitimately cheap, not just cheaper, flights, planning further in advance is the way to go. But if you've got to book last minute, just make sure you're doing so before the 21 mark.

>> Read our guides on finding cheap flights for Christmas, New Year's travel, or Spring Break or read about the best time to book a cheap flight

If you know exactly where and when you want to travel, use a site like Kayak or Google Flights to set an airfare alert and get notified if the fare drops below the current price. This works best if you have a specific location and dates, but some deals can still slip through the cracks. For example, if you set up a fare alert for Seattle to Paris, you could miss out on an amazing deal to London (which is only a short train ride away).

If you’re looking for cheap flights in the United States, be sure to search Southwest.com separately since Southwest flights don’t show up on any flight search engines. The Southwest Low Fare Calendar shows you the cheapest days for your route.

You can also find some cheap hidden fares on Skiplagged, but be sure to read up on the basics of hidden city ticketing so you know what you’ll be doing.

Budget airlines get a bad rap and some cases, it's warranted (we're looking at you, Spirit). But not all budget airlines are created equal. Several new ones, like Avelo, Breeze, and PLAY meet our standards for airlines.

Plus, budget airlines can be the best and most economical way for connecting your long-haul flight to your final destination. You may not want to fly a budget airline across the ocean, but when a flight from one end of Europe to the other costs $50, a budget airline flight gets a lot more appealing.

On foreign airlines, it can sometimes be cheaper if you book using the foreign version of their website and use a foreign currency. It's not full-proof. Sometimes there are no savings and sometimes the savings are so small as to not be worth the effort, but in other cases you can save a hundred dollars or more, so it's often worth checking. Just make sure you book with a credit card that has no foreign transaction fees.

You found a great fare. How long will it last? It's hard to say for sure! Unless it’s an advertised sale (which usually aren’t that great to begin with), there’s no public end-date on any given fare. The rule of thumb is that the better the fare, the shorter it will last.

In general you shouldn't expect most great fares to last longer than a few days. If it's a Mistake Fare, it could be gone in a few hours, or even minutes.

Okay, but how can I act fast enough to snag a great fare if you've got, you know, responsibilities and stuff? Well, there's a handy regulation called the 24-hour rule that says for flights to or from the US, airlines must allow you to cancel free within 24 hours.

So, if you aren't sure you can get time off work, for example, rather than wait to hear from your boss, you could go ahead and book the amazing deal you found before it disappears. If your boss comes back and says you can't go, as long as it's within the 24 hours, you can get a full refund.

You can also use this trick if you book a flight and the price goes down within 24 hours. Just make sure you book the new flight before you cancel the old one.