Yes, I’m tagging on to the biggest Southwest news of the day, perhaps even the week. Southwest goes to Hawaii and flights are now bookable! But, don’t get too excited unless you’re pretty close to Oakland or San Jose; Southwest’s first two departure points to Hawaii. 

Southwest celebrating a successful test flight to Hawaii — Credit: Southwest Airlines

Southwest Goes to Hawaii

Southwest will fly initially from two airports, Oakland, and San Jose. Bay Area – you win! 

First, here are the start dates – Oakland:

Southwest’s Start Dates form Oakland.

and San Jose:

Southwest Start Dates from San Jose.

Don’t get too excited East Coasters!

With the flights to Hawaii starting on 17 March, you’re probably thinking that’s a good time to start — well, unfortunately its only one flight, and for the first few days, its sold out. By the end of March, Southwest goes to 2 flights returning, however, that’s where we start to see things that may not work out so well for East Coasters.

Southwest Goes to Hawaii — Schedule at the end of March to / from Honolulu.

Now lets look at Oakland to Honolulu in May:

Southwest goes to Hawaii – Oakland to Honolulu in May.

Perhaps you’re starting to see the troubling trend?

Before I spell it out, let me offer a simple flight query from an East Coast Hub — Baltimore-Washington International Airport: 

Southwest goes to Hawaii; but doesn’t come back to Baltimore.

The Problem

Now, you’re probably thinking to yourself – wait, we already saw that flights are actually being flown out on 22 May and back on 29 May, because we just saw it with the Oakland-Honolulu search; but now Southwest is showing significantly fewer options if we want to fly from Baltimore to Honolulu.

Why might that be? For starters, going West, you can only make the one flight, because the other two leave in the 8am hour, and there’s no Southwest flight that would make it in, in time.

For the way home, we’re troubled by the fact that Southwest doesn’t fly redeyes, so they come up with no options back, since its a day flight out of Honolulu. So far as I can find, Southwest does not permit stopovers — and an overnight connection could be construed as a stopover.

So what this means is, you need to book 2 separate itineraries to get home from Hawaii, assuming you fly Southwest.

What are your thoughts? Does this turn you off of the hype around new around Southwest’s new flights to Hawaii?