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).

Today, I want to answer a reader's question pertaining to this type of booking specifically with Southwest Airlines. 

Can You Have Multiple Southwest Tickets On the Same Day For the Same Person?
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    Can I have two Southwest flights on the same day for the same person?

    Southwest Airline's booking system does not prohibit you from making multiple reservations on the same day for the same person. This makes you think that you can have multiple Southwest flights on the same day for the same passenger. 

    However, once the 24 hours mark after making your reservations has passed, you may receive a cancellation email from Southwest and a refund. The email is misleading too in a way that it says "You have canceled your reservation" while the reservation in fact got canceled automatically by the Southwest system. 

    The gist of it is, you can not have two or more Southwest tickets on the same day for the exact same passenger.

    Below is the official term and condition wording that is shown online when purchasing your Southwest flight ticket:

    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?

    Southwest Airlines' policy does not handle all the real-world scenarios. For example, you need to go to a city with Southwest Airlines on a particular day for a quick last-minute work meeting, then on the exact same day, you need to fly out of that city back to your original city to fly out with your family to another city. According to Southwest Airlines policy in regards to duplicate bookings, it will not allow that, but this is a good example that can actually happen to some Southwest flyers. 

    In this case, I suggest that you reach out to a Southwest Airlines agent to help book these types of reservations. Doing them yourself will lead to automatic cancellation by the Southwest computer algorithm.