theReport 03: Flights

Philadelphia airport

Philadelphia International Airport, Gate C22

Friends often ask me for tips on travel planning, particularly flights.  What sites do you use? When should I book? Are there better days to fly? How can I find a good deal? Bottom line, there’s no special formula. Oftentimes it takes a bit of luck and intuition to know when to make the click.

But after years of practice, here are some of my tips of the trade:


Early is the name of the game.  For me, anywhere between 6-11 months out is when I book flights and lock in better rates.  

Based on historical trends, Tuesdays and Wednesdays are the cheaper days to fly assuming you are staying over a Saturday night.  

Due to work schedules though, we tend to fly out on a Saturday morning.  There are benefits to leaving on a weekend. There’s hardly any traffic heading to the airport and most of these flights depart on time, having less chance being held up by a previous flight.  There are fewer crowds and shorter lines at the airport.  And the rates, if purchased in advance, are reasonable.  

As for the return, we also try to come back on a Saturday or Sunday. Again, less traffic driving home from the airport. Note – we live an hour away from the airport so we take road traffic into consideration. Before we lived in cities where access to the airport was just a metro stop away.  

Shoulder season has always been a very nice time of year to get away.  Fewer crowds and better rates.  We’ve had a few unlucky weather spells in the spring and fall seasons but the trip itself tends to outweigh the few rainy days.  

London Heathrow

London Heathrow


As SJ approaches grade school age, we are bracing ourselves to join summer crowds and spring breakers on full flights and packed hotels during high season.  This will be a good opportunity to use up all those miles I’ve been hoarding.  

If you decide to cash in on those frequent flier miles, seats open up 334 days prior to departure. Pull out your calendar and count backward.  Mileage seats are gradually released the closer you get to take off in hopes that most of them are purchased rather than given up for mileage.  The earlier you book, your chances improve for being seated together and securing a nonstop flight. You are required to pay taxes (take note for those flying international), so some carriers (ahem British Airways) who tend to add on ridiculous taxes to flights aren’t worth trading in all your hard-earned miles for.  Better pay the full fee and use those miles for an airline partner like American or Iberian.  

Marseille Provence Airport


For the longer haul trips, we’ll have our destination in mind a year or more before we go.  I will start tracking flights as early as 11 months, which is generally around the time the booking sights will make seats available.  

Whenever possible, I book a nonstop direct flight.  My worst travel experiences on flights have been due to delayed layovers whether it’s weather or technical issues to blame.  Even if the cost is slightly more, I would rather pay to make up for lost time on vacation.  


Lately, I’ve been using Google Flights.  You can set up alerts to let you know when’s the best time to buy based on your routing.  However, there are some limitations and doesn’t account for all carriers like Kayak.  I find Kayak’s interface not as user-friendly but it produces an exhaustive report; and if you learn to use its settings properly, you can determine the best rate based on how many stops, the duration, and time of day.  


A Kayak tool I do like to use is Kayak Explore.  It allows you to search for the best flights according to routing and the month of travel.  For instance, I once pulled the trigger on an unbelievable deal for a May trip from Philadelphia nonstop to Brussels with an open-jaw return from Prague back to Philadelphia.  We purchased a separate one-way flight from Brussels to Prague on an inter-European low-cost carrier.  Belgium and Czech Republic aren’t two locations that are commonly visited together, but given the rate, we chalked up the trip to one beer-hopping tour of Europe from lager to pilsner.

Charlotte airport

Charlotte NC Douglas International Airport


I tend to steer clear of Expedia, Travelocity and Orbitz.  I like to deal directly with air carriers for a couple reasons.  I’m always looking to score miles, even if I have to sign-up for a new frequent flier program.  Secondly,  when issues with flight delays, retrieving credit or cancellations arise, self-imposed or not, it’s much easier dealing with the airline directly rather than trying to explain the situation to an intermediary Expedia agent.  

In the past few years, I’ve been using low-cost carriers such as Spirit Airlines and Frontier for shorter domestic trips especially within our northeast to southeast region.  We scored $99 roundtrip tickets to Myrtle Beach and $69 roundtrip tickets to Charlotte from Philly.  Just one thing to note – they charge for everything else when it comes to carry-on luggage, checked luggage, snacks, certain seats.  Again, book early so you don’t get seated on the opposite end of the plane from spouse or kid (wait, is that a bad thing?).  Plus the cheaper tickets tend to go fast so get on it now.

A personal plug, I’ve had good experience with Virgin Airways for overseas flights and JetBlue for domestic.


Through the years we’ve hoarded over a million United Airlines miles and a few hundred thousand miles with American, so needless to say, we are brand loyal.  I’m still waiting for my Up in the Air moment when the captain sits next to me with champagne although I’d settle for George Clooney instead.  

Any flight tips you’d like to share? Any other travel questions I can help with? Let me know!

Here’s my Report on Vacation Rentals.

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