Why can't you fly from the east coast (or anywhere near) to Hawaii if the times work?
 

I get that Southwest is a bit odd with Hawaii flights. They don't do redeyes and such -- so getting FROM Hawaii to the midwest or further east just doesn't work -- you run out of hours... But I don't get why you can't go the other way. As an example, there is a flight from GRR (Grand Rapids, MI) that leaves at 6:30am and arrives at LAX at 12:40pm. So, pretty early in the day LAX time. There are then a BUNCH of flights from LAX to OGG (Maui) well after 12:40pm -- starting at 1:25pm through 4:45pm -- the latest arriving in OGG at 9pm (but one as early as 6:30pm).

So, how come Southwest won't let me book a flight from GRR->OGG? It would leave at 6:30AM, connect through LAX, and arrive in OGG somewhere between 6:30pm and 9pm. But when I search for that, it tells me that there are no flights from GRR->OGG on that day. Am I missing something?

Also, what if I book it manually myself? Are there any issues with that where Southwest is going to cancel that flight (like if you book two flights to the same place too close together and it auto-kills one of them)? Can I just book the GRR->LAX flight and also book the LAX->OGG flight for the same day and be fine? Or is that not allowed for some reason?

Thanks!

That is true fo not only Hawaii but LOTS of possible connecting cities. Don't know why you can't book through...they really need a build your own itinerary feature!

You can use multi-city to book these trips on a single reservation (in each direction) where there are no published through fares and WN will protect you. This topic has come up many times before -- there are many "possible" legal routings where WN either chooses not to publish a fare (as in this case) or chooses not to offer the routing on a fare because revenue management believes it can make more money by selling the flights as part of other fares. Most people are probably going to try to book a roundtrip here and when they discover there is no way back (due to lack of red-eyes), they will simply look at other carriers. While there may be some limited demand for a one-way, it's still going to require double or triple connects with crack of dawn departures (which goes back again to lack of redeyes translating in to most departures to islands being in the morning or early afternoon). Most people would likely choose other carriers given these limitations.

I just book two round trips-one RT from east coast to CA, the other from CA to Hawaii. It's a pain and I wish they would change it. Actually for our upcoming April trip I have a flight booked on Delta old miles we had instead as there's better time options. I'd love to not have to book two round trips!

As I noted above, these can be booked as 2 multi-city trips instead of 2 roundtrips. The benefit of multicity is that if there are IROPs causing a misconnect, WN is obligated to protect you since the flights in each direction are on a single reservation. There's also some potential tax savings. You only get hit with one $5.60 TSA tax in each direction for same day flights (with two roundtrip bookings you'll get hit with two in each direction) and PFC charges max out after one connection ($9.00) in each direction.

This has been this way for at least a decade - long before Hawaii service and one of the top 3 reasons I will never fly WN

You have to buy separate tickets - last time i flew them was 2012-2013 timeframe and they would check my bags thru, but you had to buy the tickets separately.

Not sure on the current situation

The ‘you can’t get there from here’ problem only gets worse when you’re starting/ending at a WN outstation and also limits the number of times I book with them since the multi city option will then price out at way more than a Legacy 3 airline

It's frustrating for not just Hawaii but for lots of cities.

And it's entirely a problem of Southwest's incompetent IT. That's the most infuriating part. The flights are there. Any other airline would let me book them. It's not a revenue management thing - they could easily load the fare as the two fares added together if they cared about fixing this.

I believe it is because the schedule is set up not to offer flights with more than one plane change. That said, it is not true that you can't fly from the east coast to Hawaii on Southwest, you just can't do it from GRR ( and I am sure other stations too).

I think that one of WN's great strengths is that you can do this, with early eastbound Hawaii departures, for example:

1/17 HNL-LAS-CMH
1/17 OGG-LAS-STL
1/17 KOA-PHX-MDW

Last one gets in at a comfortable 9:30 pm Chicago time!

Farther east:
1/17 HNL-LAX-BWI
1/17 HNL-LAS-PIT

They definitely allow and advertise itineraries with two plane changes.

Can you find one for me? Because I can't find any in the current schedule just browsing through.

We currently do not have double connects in our published itineraries. They can be built manually, but would not be a "through fare", would be the combination of two fares A-B and B-C.

This is just Hawaii that isn't offering double connects, right?

None of our published schedule currently offers double connects. There are flights with more than one stop, but only one of the stops will involve a change of planes.