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If I search for an available fight and get a message that no flights match my selected itinerary, do I have to just keep guessing dates to try to find a flight? Is there no calendar showing days when the routes are operated?
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Are you using either of these pages to search?
https://www.southwest.com/air/flight-schedules/index.html
For that first one click the "weekly" option under the view section before you click search.
https://www.southwest.com/air/low-fare-calendar/index.html
Both of those web pages should give you a good view of availability.
Also if you post the city pairs then someone may be able to help with the search.
Customer | Home airport DCA
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I would check out the low fare calendar as mentioned by SWDigits that way you can see a full month worth of dates as flight schedules change from time to time and some routes may be seasonal or weekend only routes.
-Blake