NY Times has a great blog post on how to book travel online. Here’s how I book domestic travel with defined dates:

  1. Check mileage programs – see if a saver ticket is available (generally 25k for a roundtrip). If so, book, but watch out for fees, especially if within 3 weeks of the flight.
  2. Check Kayak.com, ITASoftware.com,and Southwest.com (using multiple tabs)
  3. Redo #2 for alternate airports
  4. Redo #2  using one-ways for each leg
  5. Redo #2 searching each leg of the flight separately (including all layovers)
  6. Redo #2 for one-ways in alternate cities that use your destination as a layover. For instance, it’s possible that a ticket from Seattle to Chicago is cheaper if you book a flight from Seattle to Indianapolis with a layover in Chicago, and just don’t get on board for the second leg.
  7. Check Bing and Kayak to see if the fare is likely to decrease. If so, wait
  8. Book directly with airline of best/cheapest/shortest option

For complicated (multiple airlines and multiple legs) and/or international travel, I usually book with Expedia. They have great service and I’ve never had a problem using them.

I try never to book the last flight of the day, because it’s often canceled. I try to book one flight earlier than I need to be at a destination, because if something would happen, I’d have a 2nd option to get there. For vacations I book far in advance to lock in low rates, but for business trips and for events like weddings and sports/concerts, I try to book closer to the event because airline timetables change frequently. Generally, book no sooner than 3 months prior to an event you need to attend at a specific time.

Definitely pick your seat if you can. If you don’t, you could get a middle seat, or even bumped at an inopportune time (it happened to me). Use seatguru.com to pick a seat (the NYTimes article suggested seatexpert.com but I’ve never tried it).

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