9 STRATEGIES WHEN YOU DON'T HAVE FLEXIBILITY on flights:
1. Check fares out of close, drivable airports.
2. Check fares from nearby major hubs, like
LAX or JFK. If they're hundreds cheaper,
take a short positioning flight.
3. Check fares to airports near where you're
going and get to your final destination by
train, bus, or short budget flight.
4. Check if flying out a few days earlier or
flying back a few days later will be
significantly cheaper.
5.Even if you have zero flexibility on dates,
check a day before or after in case there
are, say, red-eye flights just past midnight.
6. Start searching as early as possible.
7. Don't wait until the last minute to book.
Flights will get more expensive in the final
three weeks, not cheaper.
8. Check Skiplagged.com for hidden-city
tickets.
9. If you've got a stash of frequent flyer
miles, see if there are any cheap award
flights
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•Travel is good medicine. Frequent travelers are healthier, happier, and more professionally successful than people who rarely travel.
• Frequent short trips boost your well-being
more than one long trip. They let you visit more places, ensure you savor vacation rather than get used to it, and give you more anticipation because the next trip is always coming up soon.
•Cheap flights alleviate the pressure to be overly frugal during the trip itself and let you do more on your vacation than if you'd overpaid for airfare.
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Flight First Method:
Step 1: See where the cheapest flights are.
Step 2: Pick one of the cheap flight
destinations.
Step 3: Pick one of the cheap flight dates.
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Always consider driving/flying to nearby airports to get a better rate.
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The best time to buy plane tickets:
Domestic Flights:
During peak season (summer, Christmas): 3 to 7 months before travel
During off peak time: 1 to 3 months before travel
International Flights:
During peak season (summer, Christmas): 4 to 10 months before travel
During off peak time: 2 to 8 months before travel
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SET YOURSELF A 21-
DAY CALENDAR
REMINDER
I recently had to book a flight to Atlanta, and
because of schedule constraints there was one specific Delta flight I needed. The fare was
decent but not great when I started monitoring
about six weeks out from travel. I checked the
flight daily, hoping that the price would come
down. But rather than continuing to monitor up
until the last day, I set myself a calendar reminder to book exactly three weeks ahead of
travel.
Why did I set that specific day as my deadline? Because the cheapest tickets regularly include a 21-day advance purchase requirement in their fare rules. Even though the ticket I was monitoring hadn't gotten cheaper in the preceding few weeks like I'd hoped it would, I booked it because I knew that the cheapest fares would expire after Day 21
Lo and behold, the day after I booked, the fare shot up by $140, and then a week later another $150 as the next cheapest fare's 14-day advance purchase requirement passed. Setting myself a 21-day deadline (and a calendar reminder to make sure I wouldn't forget) prevented me from accidentally overpaying.
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Cheapest times to fly typically: Tuesday, Wednesday, Saturday. Jan, Feb, March, Oct, Nov
••••••
But if you're a student, teacher, parent, or just someone whose ability to travel is restricted to June through August, you're stuck competing
against millions of other travelers for the most
popular seats. Apart from scouting out cheap
summer flights many months in advance, the other way to get a good deal is to travel as early or late in the summer as possible. Flights in early June or late August are significantly more likely to be cheap (or at least not egregiously expensive) than flights in July.
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SHOULD I GET TRAVEL
INSURANCE?
Some people think I'm reckless for never buying travel insurance, but I've got a good reason: My credit card's already got me covered. Many credit cards automatically carry travel protections at no cost, as long as you use the card to pay for your flight. The specifics will vary by card, but they often include compensation for flight delays Or cancellations including reimbursement for
lodging and meals, if necessary), lost, damaged, or delayed bags, rental car insurance, sometimes even foreign medical insurance. (If, like me, you find it hard to memorize your card's specifics, just Google [the name of your credit card] + travel protections.)
Because my credit card already carries travel insurance, buying additional insurance would
often be superfluous. This is especially true considering that, contrary to popular perception, travel insurance (whether you paid for it or it was included on your credit card) doesn't let you cancel a flight penalty-free. For that, you have to book a much more expensive ticket to begin with.
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SOUTHWEST
AIRBITRAGE
The minute I get a wedding invitation (or similarly inflexible event), I'll book myself a flight on Southwest. Unlike most airlines,
Southwest doesn't charge fees to cancel a ticket.
So by booking through them, I've locked in the
price and ensured that's the maximum price I'll
have to pay. If I decide not to go, I can cancel the
ticket for free. If prices drop on Southwest or a
better or cheaper flight pops up on another
airline, I can cancel and rebook. And if nothing
better pops up, I'll know I got the best deal
could.”
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Add-on fees. For the first eighty years or so of
commercial flights in the United States, checked luggage was included in the ticket price. But beginning in 2008, most airlines started charging passengers extra to check a bag. These fees have since become a massive revenue driver. In 2018, U.S. airlines collected approximately $5 billion in bag fees. They collected an additional $2.7 billion from reservation-change fees that year, and millions more from other ancillary fees like seat selection and onboard meals.
There's a hidden reason why airlines love add-on fees: They're taxed much lower than airfare. When you buy a domestic flight, the federal government levies a 7.5 percent excise tax on your fare, and airlines are required to include this tax in the fare they show you (rather than, say, the way stores don't show sales tax on the display price). Optional fees like bags and seat selection aren't included in the ticket price and thus aren't subject to the 7.5 percent excise tax. By no longer including bags in the ticket price, U.S. airlines saved $375 million in their 2018 taxes alone.
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Airlines used to primarily make money selling coach tickets. Today, airlines generate a large and growing percentage of revenue from other sources like premium seats and frequent flyer miles.
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Second, you're protected by the 24-hour rule only if you book directly with the airline. The
24-hour rule is a Department of Transportation
regulation that automatically gives travelers a
24-hour grace period after purchase during which they can cancel their ticket and get a full refund without any penalties or fees. Every
flight booking, even on foreign airlines, is protected by the 24-hour rule so long as it meets a few conditions: The flight is to, from, or within the United States. The flight is at least a week from departure. The fare was booked directly with an airline (not through an online travel agency).
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While Google Flights excels in robustness, flexibility, and speed, one drawback is that it can sometimes miss cheaper fares if they're found only on smaller OTAs. Best practice, therefore, is to start your search on Google Flights, locate the cheapest route and dates that appeal to you, and then check that flight on a site like Skyscanner or Momondo to see if there's a lower possible price.
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“When you're traveling with a group, instead of
just searching for the entire group, see if fares
are cheaper by booking one or two tickets at a
time.
In summer 2019, I searched for three
passengers from Portland to New York. Google
Flights showed a one-way fare of $178 per
ticket, an okay but not great price. When
reduced the number of passengers to two,
though, the price dropped to $117 per person.
booked those two tickets at $117, then booked
the third ticket at $178, resulting in a total cost of $412 rather than the original $534.
The reason this type of price discrepancy
sometimes occurs is that airlines want to put
your entire group into a single fare bucket. In
this case, there were only two tickets left in the
$117 fare bucket, with plenty more in the $178
bucket. Searching for three tickets priced all
three at $178, whereas searching for two priced them at $117 (and I knew I could book the third ticket for $178).
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WHAT TO DO WHEN A
FLIGHT GETS DELAYED
OR CANCELED
Three things you should always do if your flight
gets delayed or canceled:
• Do your own research: If you need to get rebooked on a new flight, rather than waiting to hear what rebooking options they present you, check the airline's (or airline partners') flight schedule to see what other possibilities would work best for your situation. You're always your own best advocate.
2. Call international customer support: When a flight gets canceled, airline agents have hundreds of people to rebook, and even more when multiple flights are impacted by bad weather. Rather than spending hours in line, what I'll do is get in line but immediately pull up a list of the airline's international customer support numbers. A Minneapolis snowstorm will tie up Delta's main U.S. phone line, but calling the United Kingdom or Singapore line is likely to get right through. It doesn't make a difference if an airline agent is in a call center halfway around the world; they can still get you rebooked. Just be sure to check if your phone plan charges for international calls.
3. Ask for compensation: Assuming your flight interruption isn't weather-related, it never hurts to send an email afterward asking
for compensation. Airlines are unlikely to offer compensation proactively, but if you follow up after a big delay and politely explain why it was a hardship, you'll almost always be given hundreds of dollars or thousands of frequent flyer miles for your trouble. (This is especially true on European flights, where regulation
EU261 requires airlines to compensate passengers for long delays and cancellations.)
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One way to make sure you're sitting with your travel companions is to fly Southwest. They use an open seating plan, and travelers are permitted on board by order of when they checked in (aside from those with elite status or who paid to jump the line). Set yourself a calendar reminder to check in exactly 24 hours ahead of your flight and you'll be certain to sit with your travel companions. If you're traveling with young children, you'll get to board early regardless.
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If you only search for flights from New York to Santorini in a single itinerary, you can expect to pay $1,500. If you break your trip up into multiple itineraries, you could get to Santorini for $334 roundtrip. At that price you could bring your three closest friends along, cover their flights (what a mensch!), and still pay less than you would have without the Greek Islands
Trick.
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In fact, depending on your final destination,
the last leg may work best on another mode of transportation altogether. Sometimes the
cheapest route to Venice is a cheap flight to Milan paired with a two-hour train ride to Venice. Many islands in Greece are accessible from Athens by ferry. (The website Rome2rio is
the easiest way to explore public transportation schedules and prices anywhere in the world. including trains, buses, and ferries.)
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FINDING NONSTOP
ROUTES
Check the website Flightconnections.com to quickly and easily see all the nonstop flight
options to or from any given airport.