There are lots of good websites with fare comparisons and tips. Check out these links. Be flexible on your departure and arrival dates and on your airports and your airlines and your hotels.
1. Start with these airfare aggregators: Kayak, Farechase, Sidestep, and Farecast. Each one searches multiple airlines, but they tend to return slightly different results. They're usually best bets for cheap flights. Farecast gives you a fare prediction (only accurate about 50-75% of the time).
2. Check the traditional discount search engines: Cheaptickets, Orbitz, Expedia, Priceline, and Travelocity. These too will return different prices for different flights. Most charge a small booking fee (see tips on your right).
3. Check Southwest (they do not share prices with above sites). Also check JetBlue, Delta, and US Airways to see if they have any site-exclusive specials.
4. Book the cheapest flight you can find above that matches your criteria. (See additional tips on this page).
Using One Way Flights
Southwest and Jetblue list separate prices for each leg of the flight. If you find that one of the legs of the flight is way is cheaper than the other, check the more expensive route via Orbitz and Travelocity as a one way fare. This way you can book two separate flights using two separate sites and get the best deal on each one way flight.
If you do book this way, make sure that each search was run within the last 10-15 minutes and book them close to the same time. You don’t want to take the chance that one reservation expires before you get a chance to book them both.
Multiple Cities
If you need to book a flight to multiple cities, there are several strategies you can take. Most booking engines allow you to search flights using a “multi-city” or “3-way” option. You should try this first to get a baseline of prices.
It’s also a good idea to break up the flight and run searches for one-way flights for each leg. Jetblue and Southwest treat all their flights as one-ways (even if you’re booking round trip), so they often have good prices for one-way tickets. Orbitz also tends to return cheap one-way flights.
Travel Tips
If you book a round trip ticket with an airline and do not make your first flight, you need to notify them if you intend to use the second half of the flight. Otherwise, they will cancel your entire ticket.
Keep in mind airport parking fees and tolls, which can really add up over a number of days. Use satellite parking when available - it tends to be cheaper. When deciding between airports, keep in mind the cost of gas - and or public transportation / taxi fares.
Some airlines will allow you to change your flight for around $50-100 to a different day if they have availability. So if you want to stay an extra day in New York City, it might only cost you $50 to extend your trip. Call the airline and talk to a customer service rep – they can often be rather accommodating.
If you fly often, sign up for frequent flyer miles with each airline. Even if you book through a booking engine (like Orbitz), you can still apply miles to that particular airline's frequent flyer account. You might also want to look into getting a cradit card (like the Delta Skymiles American Express card) that earn points when you shop - many have double points for things you buy everyday. Those points tend to add up after a while and can be used to get free flights.
If you're a student, check out Student Universe or STA Travel for discounted airfare.
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