I get asked this a lot.  I mean, I’ve gotten emails from co-workers I’ve never had a single conversation with that are like, “Hey, someone told me you can get me a cheap flight.”  Sometimes it’s true.  I don’t want to brag, but…. oh heck, I do want to brag.  For instance: a friend just told me he wanted to go to Ireland and I found him a direct flight round-trip from Chicago for $361.  While I can’t promise you to always score that good of a deal, I can give some tips.  Also, it really helps if you live near an airfare hub.

1.    Travel in winter, except for during Christmas and New Year’s.  While it’s expensive to fly domestic during Thanksgiving time, it’s a sweet time to fly to Europe. 

2.    Travel during shoulder season, more or less April – May, and September – October.  Prices will likely be more expensive than winter, but still cheaper than summer.  (Note the exception: Easter).

3.    Depart a day other than Friday and return a day other than Sunday.  Wednesday can be the cheapest day to fly, but I’ve found it varies a lot.

4.    Sign up for airfare alerts.  I used Kayak to track routes I’m interested in.  Airfarewatchdog, Farecompare,and Travelzoo also alerted me to an exciting cheapo flight.  Check your fares every day so you are familiar with what flights cost and the normal fluctuation in price.

5.    Travel “open jaw”—that is, in one city and out another.

6.    Be ready to buy on the spot.  I get my vacation days cleared in advance at work, so I’ve already got the trip time blocked out.  When a cheap fare shows up in my inbox for the correct dates, I buy it immediately.  Cheap fares rarely stick around.

7.    Weekends are almost never a good time to shop for airfare.  On average, the best date/time to buy is Tuesday afternoon, but again, see #6 and be ready to buy whenever the cheap fare appears.

8.    Clean you cookies before you shop–airline website may increase the fare if it recognizes you searching the same flight more than once.

9.    If you find an especially great deal to Europe, but it’s not your intended destination, consider buying it and then continuing on to your destination on a budget European carrier.  This is not such a great idea with a short trip, but for longer stays could work out well.  For example, let’s say I bought $361 flight to Dublin and I had a month’s vacation.  I could fly to Dublin, hang out there for a couple of days if I wanted to, and then take a discount airliner to my intended destination.  Skyscanner has a cheap flights map that you can use to find the cheapest connections.  I could enter Dublin under the departure city and leave the destination blank (selecting other one way or return flights).  Click on map next to the destination field, and the map will show orange dots to all the flights available.  Hover over the dots to see the price of the flight.  Cheap, right?  A few caveats about budget European flights: they are not always out of the main airport, so public transportation could be a more of a hassle.  Also, they are notorious for charging fees for everything, so read the fine print!

Even as a confirmed cheapskate, however, I don’t always go for the least expensive option. In the interest of sanity, I advise the following:

Rule #1: avoid changing planes in Heathrow if at all possible.  If you have to spend an extra $50 for a flight that changes in say, Frankfurt, do it.  Heathrow is a hot mess of long lines and delayed flights. 

Rule #2:  avoid Altalia, and go German when you can.  Alitila has the best inflight meals I’ve ever had…and that’s the only nice thing I can say about it.  Lufthansa and Airberlin have bland food and will get you where you  need to go with minimal drama. 

Rule #3: avoid long layovers, unless you can structure them into a mini-trip.  There are a lot of cheap flights on Turkish Air right now, but most of them have really long layovers in Istanbul, during the middle of the night.  You need to be pretty masochistic for a 24 hour flight.

So there’s no magic formula for a cheap flight, and the ground keeps changing.  Your best bet is to obsessively check fares—and do let me know if you find a great deal from Chicago.  I’m always searching.