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We are going on a cruise to Alaska and want to book a flight to Seattle. The cruise is not until August, 2018 but I wanted to get airfare ASAP. Does SWA have any kind of 'alert' system when flights are available that far out? I really want to be proactive and book the flight as soon as it is available.
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There's no alert, but you can find updates here: https://www.southwest.com/air/flight-schedules/index.html
They usually post the next schedule extension date shortly after an extension occurs. Currently the site says "We are currently accepting air reservations through June 5, 2018. On November 2, 2017 we will open our schedule for sale through August 12, 2018. This date is subject to change! Please check back frequently."