$289 Cheap Southwest Airlines flights Jacksonville (JAX) to Kahului (OGG)

Finding cheap one-way Southwest Airlines flights from JAX to OGG from $289 on Expedia is a cinch — just filter by "Price (lowest to highest)." Alternatively, check out our affordable round-trip fares from $526 for your next exciting adventure.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

For cheap Southwest Airlines fares from Jacksonville Intl. Airport (JAX) to Kahului Airport (OGG), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence the cost. Sunday is usually the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your trip on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

To find the earliest departure from JAX to OGG with Southwest Airlines, filter your results by "Morning" and "Early Morning." Choosing an early flight usually means you're less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.