I always start a flight search on a favorite travel site like Kayak or Travelocity to see which airlines offer the best flight schedules and best prices. Remember, cheapest round trip isn’t always the best. Consider number of stops and length of layovers. (I prefer 1-2 hours to give a cushion for delayed flights and to give me time to buy food, stretch and use the restroom.) Direct flights are always better for easier travel and reducing the chance of things going wrong. I’ll pay much more for a direct flight (time is money)!
SECRET: Since we go to Maui at least once it a year, my husband and I both have Alaska’s credit card so we can utilize Alaska’s Famous Companion Fare for discounted tickets for our boys. They often have a sign up special of buy one, get one for taxes and fees ($0 fare plus taxes and fees from just $22) after you make $1,000 or more in purchases within the first 90 days of your account opening. There are no blackout dates. After your first BOGO, it’s usually about $99 plus taxes a ticket. Learn more here
Alaska is my preferred airline to Maui since we can utilize the companion fare, but they also offer $100 first class upgrades if it isn’t sold out, which we’ve used a few times to have more space with a lap infant. Hawaiian and United are other airlines that usually have direct flights to Maui from the West Coast. I always try and book directly on the airline’s site if the pricing is the same as the third party sites — even if it means I have to book two one way tickets (if the best combo is on two different airlines). If flights are cancelled or delayed, you can work directly with the airline vs a third party site.