Where should I fly?

Thanks to repeated trips within California, I now have credit for two one-way tickets between any Southwest cities in the continental US. The credit expires in February 2008. Where should I go, and when?

I was thinking of visiting Portland (plus Eugene), Seattle, or Boston (plus New York), since I have friends in each of those cities.

If I start at SJC and fly to Boston or New York, in which city should I attempt to get a 2-hour layover? I don't think I'd enjoy a direct flight and I know my laptop wouldn't.

If I don't use the credit on an interesting trip, I can use it next time I visit my parents in Los Angeles. But what would be the fun in that?

7 Responses to “Where should I fly?”

  1. Scott Perry Says:

    Seattle is cool, but I vote Boston/NYC. Fantastic area.

    If you have to layover, try to get it in Denver or one of the newer airports in the country (dunno which airports in the middle-country are hubs though…). Do your research, a select few airports have key amenities like free wireless…

  2. Jesse Ruderman Says:

    There are airports with free wireless!?

  3. Albert Wang Says:

    Don’t forget to compare the prices to those offered by Ding! SJCLAX was on sale for $25 one-way this weekend.

    And if you aren’t able to find a cool trip, consider selling your tickets, too.

  4. Gerv Says:

    It’s interesting how our approaches to flying differ. The idea of flying from London to San Francisco with a layover horrifies me – even that far, I’d much, much rather fly direct than twiddle my thumbs in some airport. Whereas you consider a layover a feature even on a flight with a total flying time of four hours.

  5. Jesse Ruderman Says:

    Where do you see four hours? Expedia says SFO to BOS is five and a half hours.

  6. Akshay Says:

    SJC NYC is 5.5 hours. Fly direct, don’t purposely attempt a layover. If you’re worried about laptop juice, then buy an extra battery and swap mid-flight. JetBlue’s terminal in JFK has free wireless (as does the LGB airport) but they’re kinda flakey.

  7. Jeri Says:

    I vote Seattle partly b/c I’m so sick of the northeast. I can’t wait to go to California next year but maybe you feel differently… if you go to Boston/NY, go right now or in August/September because that’s when the weather is best.
    I agree that you should take a direct flight if you can — I hate layovers, they’re such a waste of time. oh keep in mind if you do have a layover, you can’t use your laptop 20 minutes after taking off, and until landing (40 minutes of pure boringness), it also takes 20 minutes for all the slow people in front of you to get off or board the plane (40 minutes of annoyingness-is that even a word), etc.