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I am wanting to book a flight for my husband and I to go to our son's Marine boot camp graduation. It is possible that the dates may need changed. We want to go the less expensive way "want to get away" prices. Can we change our dates? Is there a charge? Can I get flight insurance?
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Yes you can change. At Southwest, you may pay a difference in air fare, but never a change fee. Also if you don't go at all and cancel your trip you will have a $$ credit for the full amount that will be good for 1 year from the date of purchase.
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The "WGA" fares may not be available really close to the date of travel, I'd suggest to consider when you might need to change things - if you are looking at months or weeks of advanced notice, you should be in good position to change. There's no change fee, you only pay the difference in fare.
The wrinkle is that a same day change or only a few days ahead may have larger fare differences if all the WGA fares are taken and only Anytime or Business Select remain.
Instead of flight insurance SW will allow you to cancel the flight and hold the funds as a voucher for future use (no change fee) that has a one year expiration.
You can probably get some third-party trip insurance but hopefully the flights are cheap enough and SWA's flexibility is enough that you don't need it.