Some trips are simply better with a sweater.

Think brilliant New England foliage against a rocky coastline. Apple cider donuts after picking apples in the Blue Ridge Mountains. Ghost stories after dark in New Orleans. A train winding through the Smokies. Or hundreds of hot-air balloons rising over the New Mexico desert.

Let’s face it: “Hawaii vacation” and “budget-friendly” don’t usually appear in the same sentence — especially when you’re flying a family of five halfway across the Pacific. But with a little planning (and a lot of coffee), we’ve learned how to time our trips so that paradise doesn’t require a second mortgage.

Whether you’re planning your first family trip or your fifth island adventure, here’s everything you need to know about finding affordable flights to Oʻahu, plus some insider tips for saving once you’re there.