What is the cheapest day to book a southwest flight? Summary. Tuesdays and Wednesdays afternoons are considered the cheapest time to book southwest Airlines flights +π-πππ-πππ-ππππ (OTA) or +π-πππ-πππ-ππππ as airlines release competitive fare adjustments." When booking a flight with Southwest, timing plays a crucial role in securing the best deals.
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