When booking a flight my first concern is most often which airlines fly direct and how can I get to my destination as quickly as possible. If you have a bit of flexibility with your dates of travel or length of trip you may be able to turn a flight option that contains a layover into an even better trip than you’d originally planned.
For some reason you can often find flights that contain layovers and connections cheaper than you can a direct flight, primarily for routes that have little competition because the one or two airlines that do fly that direct route jack up prices to get as much cash as possible. Particularly for cases where you can find a flight with a connection that is cheaper you may be able to turn into a mini-vacation on the way to your destination.
As an example, flying from Boston to San Diego you have the following options when searching Kayak and Expedia:
1 stop: $241
If you book this exact same trip as a multi-leg trip for these cities (Boston to Houston to San Diego to Boston) it is priced at $1,112. So, by booking slightly differently you save $871 for the exact same flights.
For this route you have the option to visit any of these cities: Houston, San Francisco, Los Angeles, Newark and Dallas. It is important to keep in mind that you don’t want to choose a city where you need to rent a car or spend hours (or a lot of cash) traveling back and forth from the airport in such a short time.
These price differences are a bit crazy, but then again, so is much of what happens in the airline industry. If you choose a flight that has a layover you can select one that is convenient to the airport and spend the difference on getting to know this other city on the way. You can also try selecting a connecting flight on the following day so that you use that $100 toward a hotel room in your layover city. For the same price you’re now adding an additional city that you can visit on your trip.
This also works if you know in advance that you plan on visiting more than one city. Try searching for only flights that do have connections. There may be an airline out there with a flight that can connect through one of the cities for you. This can save you quite a bit instead of booking a multi-leg trip.
This doesn’t just go for domestic flights. For instance, if you are planning a trip to Barcelona from the US, maybe you want to fly on Delta / KLM which will connect through Amsterdam. Make that layover last 24 hours and you can visit Amsterdam without paying any transportation fees on your way to Spain.
Check out also how you can save money on booking a roundtrip flight instead of a one-way ticket.