Yes, you can absolutely use a Southwest Airlines Companion Pass to fly to Hawaii, which remains one of the highest-value ways to use the perk in 2026. Once you have earned the pass by flying 100 qualifying one-way flights or earning 135,000 points in a calendar year, you can designate one person to fly with you for just the cost of taxes and fees (currently $5.60 each way for domestic U.S. travel). This applies even to Southwest's long-haul routes from the West Coast (Oakland, San Jose, Sacramento, Los Angeles, San Diego, and Las Vegas) to Honolulu, Maui, Kona, and Kauai. There are no "blackout dates" for the Companion Pass, meaning if there is a seat available for purchase, you can use your pass to bring your companion, even during peak Christmas or Spring Break periods. However, you must first book your own seat (either using cash or Rapid Rewards points) before you can add your companion to the reservation. This makes Hawaii an incredibly affordable destination for couples or families who can leverage the pass to essentially get "2-for-1" airfare on some of the most expensive routes in the airline's network.