Hi
I am making plans to go to Oahu in October. Planning the flight is a pain.
There are 3 airlines that go to 3 different airports for layovers. Which is the less evil in terms of being busy, walking to a whole different concourse, etc
St. Paul, MN
Atlanta, Ga.
Houston, Tx.
I am waiting for Southwest to announce their October fares, but looking at the others as a fallback. For SouthWest, I could fly non stop to Las Vegas, then perhaps have a 4 hour layover according to a rep.
Any advice?
The major hubs in the U.S. are about the same. They're huge operations, and there are plenty of places to eat between flights. The distance between gates is a matter of luck, depending on your actual gates. This includes the major hubs that you've listed, as well as other major hubs such a Chicago-O'Hare and DFW. (Well, Miami can be awful, but that's not one of your options.)
Some people have their favorite hub airports, but this probably has more to do with familiarity and airline loyalty than with one being much "less evil" than another.
When the weather cooperates, the big hub airports are fine. When there's a serious weather issue, any of them can be a nightmare.
However...
There's a huge risk in using two different airline tickets on the same day. If your first flight is delayed for any reason (even reasons beyond your control) and you miss your second flight, the second airline considers it to be your fault. Typically, after two hours, your roundtrip ticket on the second airline is cancelled and loses its entire value if you were unable to notify them in time. Even if you arrive only one second after the door to your second flight is sealed, you're at the airline's mercy, flying standby on a later fight.
You're much better off being ticketed on a single ticket if you're connecting (either on a single airline or on two airlines with an interline agreement). Then, if your first flight is delayed, the airline will confirm you on another flight to your destination.
With a "real" connecting ticket, the airline at your originating airport has an obligation to get you to your final destination. For example, if you have a connection on American through DFW, but DFW is a mess due to weather, American may but you on a connection through Chicago instead. But if you have a separate ticket to an intermediate airport, the airline at your originating airport only has an obligation to get you to that intermediate airport -- even if they get you there late (such as five hours late).
Two separate tickets can also be a problem if the flight times change on one ticket. With a "real" connecting ticket, your entire ticket will be adjusted if a schedule change causes the connection time to become too short, too long, or impossible.
Also, with a single ticket, your luggage will be transferred for you at your connecting airport. You'll usually stay within the secure part of the airport, and you'll avoid the baggage claim and ticket counter at the connecting airport. You'll retrieve your luggage at your final destination.
By the way, "real" connecting tickets are usually (but not always) cheaper than buying two separate tickets.
Southwest Airlines is often a great choice when flying from one Southwest Airlines city to another. But Southwest does not have interline agreements (except possibly with ATA), so I would avoid using Southwest as part of a larger itinerary.