How to Find Dirt Cheap Airline Deals
How to Find Dirt Cheap Airline Deals
How to Find Dirt Cheap Airline Deals

A few people have approached me recently seeking advice about how to find cheap flights. The truth is, there’s no magic pill. Finding deals is directly correlated to your booking flexibility, and how far in advance you begin searching for flights.

For example, Bradley Airport might be offering a killer deal to Ireland, but that’d mean driving there all the way from Boston. And it might be $100 cheaper if you flew in March instead of May, and booked two months in advance instead of three. It’s a give and take, and there’s always a risk you might miss a deal if you don’t immediately pull the trigger.

Another approach to flying for cheap is to cram a few cities into one flight. If you’re going to London for a week, make a pitstop in Iceland for a few days (airlines with layovers offer deals to promote tourism). Stretch out your layover to increase the amount of time you have to explore.

Also, keep an eye out for upcoming airlines or new direct flights from airports, which are often promoted by huge discounts. I flew to Ireland and back from Providence for under $500 by taking advantage of one of these deals.

For those who don’t wish to do the legwork described above, there are a few websites out there that curate cheap flights – namely and

Skiplagged sells ‘hidden-city flights,’ which are cities that a long-distance flight might stop in for a layover.

For example, say you wanted to fly to Baltimore from Boston. Instead of booking direct for say $300, Skiplagged sells you a ticket from Boston to Detroit for $100, with a layover in Baltimore.

Buy the ticket to Detroit and jump ship in Baltimore with $200 more in your pocket. And while the flight attendants ring last calls desperately searching for you (the missing passenger), you’ll have already arrived at the hotel.

A few years ago a couple of large airlines tried to shut Skiplagged down. Apparently, though, that didn’t work because the site is still in operation.

I often browse this website imagining where I might go next. Users enter travel dates and a departure city, spits out the cheapest flight options available anywhere in the world.

As an example, I just punched in Boston as my departure city with travel dates from Jan. 28 to Feb. 4. The cheapest notable places I could travel to on those dates from that place are Iceland for $246 and Sweden for $270. It’s a ridiculously cheap option for the flexible and adventurous traveler.

Of course, all of these ideas and both websites pose risk. There’s a chance you might miss a flight, or lose baggage (with Skiplagged, you can’t check bags because they’ll go all the way to the final destination). So travel smart, plan ahead, and know the risks.

Google flights

Someone just alerted me to Google flights ( as an option for those seeking cheap travel. Apparently, you can set up alerts to find the best travel dates and cheapest locations.

Finally, and this is advice I’ve put into action myself, if you’re looking for an adventure, let the cheapest flight options dictate where you go instead of the other way around. Find a cheap flight, and go there. Good luck!

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