From time to time, travelers are trying to be proactive and start looking to buy flight tickets to lock in good airfares before they even have a concrete traveling schedule. This leads to speculative bookings for different pair cities or traveling times for the exact same date for the same passenger(s).
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Can I have two Southwest flights on the same day for the same person?
Prohibition of Multiple/Conflicting Reservations: To promote seat availability for our Customers, Southwest prohibits multiple reservations for the same Passenger departing from the same city on the same date, or any multiple reservations containing conflicting or overlapping itineraries (such as departures for the same Customer from multiple cities at the same time). Furthermore, without advance notice to the Passenger or purchaser, Southwest may cancel such reservations, or any other reservations that it believes, in its sole discretion, were made without intent to travel. With the exception of Southwest gift cards, funds from proactively cancelled reservations by Southwest will be returned to the original form of payment. Reservations paid for with a Southwest gift card will have the amount applied from the gift card held as travel funds for use by the Customer on a future Southwest Airlines flight.
Does Southwest prohibit multiple same reservations for the same passenger on award tickets too?
Yes. It does not matter what kind of payment form you use to purchase Southwest flights. If you use Rapid Rewards points to redeem for multiple overlapping itineraries for the same passenger, Southwest will automatically cancel the reservation and refund you the points and taxes that you paid. See below:
Furthermore, without advance notice to the Passenger or purchaser, Southwest may cancel such reservations, or any other reservations that it believes, in its sole discretion, were made without intent to travel. With the exception of Southwest gift cards, funds from proactively cancelled reservations by Southwest will be returned to the original form of payment. Reservations paid for with a Southwest gift card will have the amount applied from the gift card held as travel funds for use by the Customer on a future Southwest Airlines flight.
What if I need to book two one-way Southwest tickets on the same day?
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