Book Southwest Flights Starting at $59: May 2025 Sale Explained

Southwest Airlines Sale Details

April showers bring May… flights with Southwest Airlines sale starting at just $59. The sale, which must be finalized by 11:59 p.m. PT on April 20, is valid on travel on Tuesdays and Wednesdays throughout the continental United States, Hawaii, Puerto Rico, and beyond during the summer and fall, according to the airline. To fly, travelers must secure their seats at least 21 days prior to their scheduled departure.

Interior of a Southwest Airplane
Ashlee Duncan/Courtesy of Southwest Airlines

Valid Travel Dates

In the U.S., including Hawaii, the sale is effective for travel from May 2 through May 24 and then again from August 8 through November 1. For international flights, travel to and from Puerto Rico, and flights from Hawaii are valid between May 2 and May 24, resuming again from August 15 through November 1.

Popular Domestic Flights

Fly between cities such as:

  • Atlanta and Nashville
  • Austin and New Orleans
  • Chicago and Cincinnati
  • Los Angeles and Las Vegas

These flights start at just $59 each way. Additionally, travelers seeking to cross the country can find flights between New York and Los Angeles beginning at $191 each way or between Boston and Long Beach starting at the same rate.

Inter-Island Flights in Hawaii

Moreover, travelers can save on inter-island flights in Hawaii, with journeys between Honolulu, Maui, and other locations available for just $39 each way. This reflects Southwest’s efforts to enhance cheaper island hopping options.

Southwest’s Network Expansion

Southwest has recently expanded its network, adding four new routes to its fall schedule in Kansas City, MO, and Long Beach, CA. Additionally, they are increasing the number of flights from Denver.

Upgrades to Onboard Experience

Furthermore, Southwestern is improving the onboard experience with enhanced Wi-Fi and exciting new beverage options. They have introduced Community Coffee’s Espresso + Cream iced coffee for a refreshing in-flight experience. The airline is also modernizing its fleet, working to implement amenities like USB A and USB C charging ports at every seat, along with larger overhead bins.

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