southwest OAK to HNL
Rating: All-Star
Flying to Honolulu with kids can feel like a test of endurance. Long lines, cranky passengers, and the constant worry that your toddler might melt down at 30,000 feet. But our recent trip from Oakland (OAK) to Honolulu (HNL) with Southwest Airlines turned out to be the opposite—it was one of the smoothest, most family-friendly flights we’ve ever taken.
First off, Oakland International Airport deserves more credit. Compared to the stress and pretense of SFO, OAK is refreshingly straightforward. Parking was easy, security was quick, and there was none of the “grand international hub” chaos that makes you feel like you’re competing in some Olympic-level airport obstacle course. It was in-and-out, no drama, just the way parents with kids need it.
Then there’s Southwest. Say what you want about no assigned seats, but when you’re traveling with family, they just get it right:
Family boarding meant we got to sit together without awkward seat negotiations.
Free checked bags gave us room for extra snacks, toys, and swimsuits without sweating over fees.
And maybe best of all—we weren’t alone. The cabin was full of other families headed to the islands, which meant the occasional cry or scream wasn’t a big deal. Everyone was in the same boat—or plane, in this case. There’s something comforting about being surrounded by parents who understand, instead of side-eyeing every toddler noise.
The flight itself was easy. The crew kept things light and friendly, the kids had their tablets and snacks, and before we knew it, the Pacific was below us and Honolulu was on the horizon.
Flying with kids will never be “perfect,” but flying Southwest out of OAK felt like the closest thing to it. Simple airport. Family-first policies. And a plane full of people who made us feel like we belonged there, chaos and all.
If you’re heading to Hawaii with a crew, skip the headache of SFO. Start at Oakland, board Southwest, and you’ll land in paradise already feeling like the trip is off to the right start.