Does Southwest Airlines fly to Hawaii - Southwest Airlines brings its signature low fares and customer-friendly policies to Hawaiian travel, offering nonstop and connecting flights from multiple U.S. cities to Oahu, Maui, Kauai, and the Big Island. With service from gateway cities like Los Angeles, Oakland, San Diego, and Phoenix, Southwest makes island-hopping accessible and budget-friendly. The airline stands out with its two free checked bags policy, no change fees, and open seating that eliminates stress over assigned seats. Travelers can easily book inter-island flights between Hawaiian destinations, leveraging Southwest’s straightforward pricing and frequent sales. The airline’s Rapid Rewards program lets you earn points toward future flights, and the coveted Companion Pass allows a designated travel partner to fly free for nearly two years. For the best deals, book early and watch for seasonal promotions, especially during off-peak months. With its no-nonsense approach and aloha spirit, Southwest delivers a hassle-free way to explore Hawaii’s paradise without breaking the bank.