Southwest adds new flight options from Las Vegas to Hawaii

While Southwest Airlines (LUV) has been flying since 1971, the Dallas carrier only recently introduced redeye flights.

That decision came down both to an old-school reservations system that did not allow for flights that took off on one day and landed on the next and to prioritization of shorter flights between regional cities. (The reservations system eventually was upgraded.)

But as investors increasingly pressured the carrier to be more profitable, Southwest announced its first redeye flights in September 2024.

The first flights will run from Las Vegas to Hawaii’s Honolulu and Kona in February 2025 followed by flights to the two island capitals from Phoenix by April. Southwest will also run these red-eye flights in 2025.

Southwest Air adds new redeye flights

This week, the airline said that it would add 13 redeye routes to its roster by June 2025.

The new routes include flights from Southern California’s Long Beach and Orange County as well as Portland, Seattle and San Jose to Baltimore/Washington Thurgood Marshall International Airport.

Also to be scheduled: Flights to Honolulu from Los Angeles, to Kauai’s Lihue Airport from Las Vegas, and to Orlando from Sacramento.

While not a redeye, Southwest is also introducing an entirely new route between Colorado Springs and Cancun International Airport.

This is the first time the airline will offer service between these two cities. It currently offers nonstop service to the Mexican resort town from places like Denver, Phoenix and Orlando.

‘Service from Hawaii and West Coast traveling east’

“The schedule includes additional redeye flights, popular seasonal routes, and more nonstop flights connecting customers to high-demand destinations throughout the Southwest network,” the airline said in announcing the new schedule.

“The airline’s summer 2025 schedule now includes 33 overnight flights with service from Hawaii and the West Coast traveling east to various key Southwest cities.”

The redeye flights will run both east to west and west to east; all will run on either Boeing 737-800 and 737 Max-8 (BA) planes multiple times a week.

On top of the new red-eye flights, Southwest is also bringing back a number of seasonal routes that it ran at different points in its history but were eventually discontinued for varying reasons.

These include flights between Austin and Boston, Baltimore and Portland, Dallas and Seattle, and Denver and South Carolina’s Myrtle Beach.

Elliott Agreement With Southwest

The focus on redeye flights reflects an effort to fly the same planes more often and to tap into new profit streams.

It comes after a major Southwest Air investor, the hedge fund Elliott Management, was looking to oust Chief Executive Bob Jordan because of what it saw as “poor execution and leadership’s stubborn unwillingness to evolve.”

The question was supposed to be put to a shareholder vote but Southwest and Elliott reached an eleventh-hour agreement by which Jordan stayed CEO. Southwest also agreed to add five Elliott director candidates to the board, and said Pierre Breber, former CFO of Chevron, would join the board as well.

“I’m not sure many people are clamoring for overnight flights,” Gary Leff wrote for the aviation site View From The Wing when the airline first announced the planned change in 2023. “However, it would improve aircraft utilization, and more capacity also supports lower fares in the market.”