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Digging Out the Best Airfare for a Complex Itinerary

Finding the “best” airfare for even a simple round-trip can sometimes be tricky, and looking for a good deal on a more involved trip can be quite a challenge. One reader asked about an upcoming tricky trip:

“My wife and I plan to fly from Chicago to U.K. next year, spend a few days with my sister, who lives near Stansted Airport, then fly to Rome, visit Cinque Terre, and return from Milan. We would normally fly nonstop on each of those three flights. But might we be better off to fly into a connecting airport such as Amsterdam, Paris, or Frankfurt, and connect to Stansted, then fly from Stansted to Rome, and return from Milan, or to fly back via the connecting airport? I thought these options might keep cost down and avoid London’s Heathrow airport.”

Although this question deals with a specific itinerary, it illustrates strategies that can apply to just about any journeys beyond simple round-trips. And it actually raises two completely separate issues.

Scoping Out an Itinerary

On any itinerary, you have to start by comparing the realistic alternatives available at the time:

  • The first step is always to price the simplest itinerary—on a single booking with direct or nonstop flights—the trip you would buy if price were no object. That figure becomes the baseline against which you measure all other possibilities. At this stage, ignore airport preferences.
  • If you prefer a specific arrival or departure airport, recheck the baseline itinerary, but limit your search to the preferred airport(s) where you need to.
  • Then, start finagling. Rather than a single itinerary, your next approach is almost always an open-jaw ticket to your first destination city and from your final destination city. You can often find low-fare flights (or even train trips) to fill in the “open” part or parts of the open jaw for less than you’d pay as part of a single ticket. Lots of low-fare airlines sell cheap point-to-point one-way tickets within most of Europe and Asia. If you don’t know the destination territory all that well, several websites, such as Which Budget, identify low-fare airline options worldwide, with links to these lines’ home sites.
  • On trips to Europe, I also sometimes try connections from U.S.-to-Dublin flights on Aer Lingus, with ongoing low-fare connections on Aer Lingus, EasyJet, or Ryanair from/to Dublin. Aer Lingus usually has good fares (although it no longer offers its cheapest fares on a one-way basis) and, by next year, you’ll be able to pass through all U.S. customs and immigration facilities in Ireland and arrive in the U.S. as on a domestic arrival. On the downside, however, Ryanair is a miserable airline to fly, with minimal legroom and fees for just about everything; EasyJet is also spartan but better than Ryanair. I don’t know a comparable situation in Asia.

Whenever you add a connection to/from a transatlantic flight at a European or Asian hub, you add a minimum of four hours to your travel time, even if you find a connection on a single airline or alliance. You lose even more time with a low-fare connection, which requires you to collect your baggage, pass through both arrival and departure processes, and re-check your baggage. Also, many European and Asian low-fare lines assess stiff fees for even one checked bag, and most travelers would have trouble trying a three-week European trip with just a carry-on bag.

Our Reader’s Trip

Our reader’s time frame of “next year” is uncertain, but because it’s far too early to get a fix on summer airfares, I looked at a trip in February—three weeks, February 2 to 23:

  • The baseline would be a single multi-stop ticket Chicago-London-Rome, with a gap, then Milan-Chicago. Expedia priced this itinerary at $685, with all flights on British Airways. This itinerary required arriving at Heathrow Airport, with no alternate London airports available.
  • For the same itinerary, but arriving in the U.K. through Stansted rather than Heathrow, Expedia’s lowest fare was $1,900—a ridiculous fare, and a ridiculous itinerary, requiring changes in both Munich and Dusseldorf. For Stansted, you can forget the single ticket.
  • Next, I looked at an open-jaw Chicago-London/Milan-Chicago, filling in with a low-fare flight from Stansted to Rome. Here, Expedia priced the open jaw at $679 or $679 on several lines, but again available only through Heathrow. Your guess is as good as mine as to why the simple open-jaw costs more than the three-flight ticket.
  • For arriving through Stansted, Expedia posted a British Airways fare of $762, but the flight from the U.S. to Stansted required connections at both Munich and Dusseldorf and took 15 hours, compared with the nonstop time of about eight hours. The fare for the fill-in flight from Stansted to Milan, on Ryanair, started at $56 with the minimum of fees (1 checked bag).
  • My final check was Chicago-Dublin round-trip on Aer Lingus ($479) plus Dublin-Stansted ($42), Stansted-Rome ($56), and Milan-Dublin ($56) on Ryanair. The total, $633, was the lowest I could find.

Our reader has only two reasonably priced alternatives: the single-ticket baseline option, with the best flights and minimum connection, but possibly a hassle for his sister, or multiple tickets through Dublin, with connecting flights for a slightly lower fare, major hassle and extra flight time, but it does get him to Stansted. I know what I’d do: Take the baseline itinerary through Heathrow, and find my own way to my sister’s house. But that’s a personal choice.

Again, these figures apply to a ticket booked in late November for travel if February. The balance could be completely different for travel in the summer—or even maybe next week.

What’s With This “Avoid Heathrow” Business?

You’ve probably seen those “avoid Heathrow if you possibly can” suggestions in lots of travel stories, especially for business travel. Unfortunately, Heathrow’s bad reputation, well deserved as it might be for some travelers, does not apply universally. There are really only two good reasons for avoiding Heathrow:

  • “Stay away from Heathrow” is generally good advice for anyone who has to make an onward connection to Europe, Africa, the Middle East, or Asia. From all I can gather, connections are a hassle there, especially when you have to change terminals. If you can arrange a comparable itinerary and fare some other way, you’re better off connecting somewhere else. Amsterdam and Munich are probably the best options, followed by Frankfurt. Paris is fine for connecting between Air France flights, but a real hassle if you have to change terminals.
  • “Stay away from any U.K. airport, including Heathrow” is good advice for anyone returning to the U.S., if itinerary options permit an alternative. In a fit of overzealous environmentalism, the Brits have decided to penalize air travel by imposing draconian fees on all air tickets for flights out of the country, and especially on long-haul flights. You’d have to pay about $75 extra to the U.S. East Coast, about $85 to the West Coast, compared with other gateways.

But for an ordinary arrival in the U.K., I don’t see Heathrow as much worse than any other big-city airport. And you have good public transport options to central London.

(Editor’s Note: SmarterTravel is a member of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns

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