Positioning Flight Example - Square

How Positioning Flights Add Logistics but Save Time and Money

If you’re planning a trip and looking for flights, it’s natural to just search your home airport to your destination and back. You’ll likely compare airlines, see what’s cheapest or most direct, but I encourage you to think beyond points A and B and see if a positioning flight might make more sense instead.

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What’s a positioning flight? Simply put, it’s an extra flight on either the front or back end of an itinerary for the purpose of saving time or money.  

Here’s a couple reasons to book a positioning flight:

Saving Money

If you want to fly to Japan, look at the prices of flights from both your home city but also West Coast airports, such as LAX, SFO, SEA, etc. Living in Chicago, it may be much cheaper for me to book a domestic flight to the West Coast and then fly from there to Japan on a separate ticket.

Saving Time

Later this year I’m taking a trip to Copenhagen but there were no reasonable flights that left after 7:30PM out of Chicago. I end work at 5PM so any flight before 7:30PM involves missing work, and my PTO is precious so that’s pretty much off the table. However, there’s a flight out of Detroit that leaves at 9PM, so I booked it and will purchase a separate flight from Chicago to Detroit the night before and work remotely from a hotel the next day before flying across the Atlantic. I still get to arrive in Denmark as planned without missing any work: a win-win. In this case, I won’t be saving money, but it works best with my schedule.

Copenhagen positioning flight example

Better Point Redemptions

Another great reason to book a positioning flight is if there’s not great award availability from your city but there is from somewhere else. For example, later this year we’re flying from SFO to Singapore on points (in business class!). There were no reasonable reward flights available from Chicago, so booking a separate flight to SFO made sense for us to get to enjoy an otherwise out-of-reach flight.

Getting Around Weather

It’s hard to plan for this far in advance, but if needed, you can reroute your itinerary and book a positioning flight to get out ahead of the weather. In December, a winter bomb cyclone was hitting the Midwest the day we were supposed to leave for Japan, so we got AirCanada to agree to rebook us out of Los Angeles and we flew from MDW to LAX a couple days early, working remotely while we were there.

Weighing Costs and Benefits

Scales of justice

Positioning flights aren’t always the best option, but are usually worth exploring for international destinations (I haven’t seen many great examples for domestic trips). Each airline has its own hub, so be sure to keep those airports top of mind when searching.

When you see that a flight is (for example) $500 cheaper out of another city, be sure to factor in the cost of an additional flight and hotel night. If those are going to add up to more than $500 (and you’re only booking this flight for the cost savings), it’s not a good deal!

The savings can be easier to justify if you’re traveling with someone else. While you may pay for 2 flights, you can get away with just 1 hotel room for a night. If you happen to have the Southwest companion pass, your partner can fly free and then you only have to budget for 1 ticket and 1 hotel room.

There are a few things you should keep in mind when considering adding an extra leg to your trip:

More Flights = More Chances of Things Going Wrong

The biggest downside to positioning flights is that any additional fight between you and your destination is another chance for things to go wrong: delays, cancellations, weather, mechanical issues, lost luggage, etc. Not to mention it’s more logistics to deal with booking another flight and hotel. This can be worth it, but know what you’re getting in to ahead of time!

If you don’t live near a major airport, a positioning flight may be a necessity more often than not. I’m lucky to live near 2 major airports, so usually adding extra legs to my trip is a choice, not a necessity.

Allow Plenty of Time

I would be very hesitant to book a positioning flight on the same day as my other flight because all it takes is one delay for your trip to unravel. Because the flights are on separate tickets (and likely different airlines), you’re on your own if you miss your 2nd flight because the 1st was delayed. Give yourself plenty of time (and maybe an overnight layover).

If you do book flights on the same day, you may be required to exit the airport and pick up your checked bags (if applicable) before going back through security since your flights will be on separate tickets. This is where TSA PreCheck, CLEAR, and Global Entry can come in handy to save you time.

Make the Most of Your Layover

If you’re going to utilize a positioning flight, it doesn’t have to be dreadful – you can make the most of your time in that area. In a couple of months, I’m taking a positioning flight to JFK on my way to Europe and am so excited to stay at (and work remotely from) the TWA Hotel in an old terminal at JFK. When we spent a couple of days in Los Angeles on our way to Japan last month, we went to our favorite restaurant one night and Santa Monica pier the next, so it became a mini vacation of its own.  

Realistic Positioning Flight Example

Here’s a very feasible example. Let’s say you live in San Antonio and want to go with your friend to Zurich, Switzerland. I picked a random week in September for the example (September 8-17). Flights from San Antonio to Zurich will currently cost you at least $2844 (all prices are for 2 people).

Example search of a flight from San Antonio to Zurich, Switzerland

However, if you booked a round trip from San Antonio to Boston the days before and after for $497.

Example search for a positioning flight from San Antonio to Boston

Then you could book a roundtrip from Boston to Zurich in between for $1575, saving $776.

Example search of a flight from Boston to Zurich. If you don't live in Boston you could add a positioning flight to get there.

An extra hotel night on either end would cost about $200/night, still leaving ~$375 in savings. Since the Boston airport is so close to the city, you could put that money to use by seeing a game at Fenway Park or getting some clam chowder at Faneuil Hall (or just putting it towards more epic adventures while you’re in Switzerland).

Example of a hotel in Boston that is cheap enough to make a positioning flight worthwhile

Most often, I just using a positioning flight at the beginning or end of my trip, not usually both, but play around with the various options and see what makes the most sense both in terms of cost savings and logistics.

I’m personally taking at least 5 trips this year with positioning flights on at least one end of the trip. If there’s a place I really want to go, I am willing to explore all options to how to get there to maximize my PTO and save some money in the process.

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