2:45 AM Red-Eye: Southwest Airlines' 5 Worst Flights To Avoid Revealed [Map]

Credit: Shutterstock | Simple Flying Published Jul 20, 2026, 12:13 PM EDT Luke has over a decade of experience as a travel writer and aviation analyst. As a passionate traveler based across the Middle East and Asia, Luke offers strong insights into the industry. Based in South East Asia. Sign in to your Simple Flying account Southwest Airlines recently scheduled its latest departure time to date, a 2:45 AM flight from Las Vegas' Harry Reid International Airport (LAS) to Honolulu International Airport (HNL). The westbound overnight service, which the carrier describes as a "reverse red-eye," was announced as part of its spring 2027 schedule and will be Southwest's first overnight flight operating from the mainland to Hawaii. The newly announced service adds to a growing number of post-midnight departures across the carrier's network. Southwest only began operating red-eye flights in February 2025 — data from aviation analytics company Cirium shows it now has over a dozen routes departing after midnight, with its latest departure times concentrated out of Las Vegas and Phoenix Sky Harbor International Airport (PHX). Southwest's 5 Latest Red-Eye Flights Credit: Shutterstock Southwest announced its latest-ever flight on July 16, with tickets already on sale ahead of a March 12, 2027 launch. The service — which is scheduled to operate four times weekly — will depart Las Vegas at 2:45 AM and arrive in Honolulu at 6:10 AM local time, with a block time of six hours and 25 minutes. Southwest is not the first carrier to operate late-night between these two airports; Hawaiian Airlines operates a similar red-eye service from Las Vegas, departing at 1:55 AM for a 5:25 AM arrival in Honolulu. Loading map… Drag to explore According to schedule data, Southwest's five latest departure times between now and next March all operate out of Las Vegas and Phoenix. After the 2:45 AM Las Vegas–Honolulu service, in second place is a 1:45 AM departure from Phoenix to Chicago Midway International Airport (MDW), followed by Las Vegas services to Dallas Love Field (DAL) at 1:25 AM and Houston Hobby Airport (HOU) at 1:15 AM, along with a 1:10 AM Phoenix to Nashville International Airport (BNA) flight to round out the top five. Southwest's Growing Late-Night Network Credit: Denver International Airport In line with its company-wide transformation initiated in 2024, Southwest began its first-ever red-eye flights in February 2025, ending a 50-year tradition of grounding its fleet overnight. Its first red-eye services out of Hawaii began in April 2025, and by June, the airline had expanded its overnight schedule to 33 daily flights. Southwest's 5 Latest Red-Eye Flights Route Departure Time Las Vegas (LAS) to Honolulu (HNL) 2:45 AM Phoenix (PHX) to Chicago Midway (MDW) 1:45 AM Las Vegas (LAS) to Dallas Love Field (DAL) 1:25 AM Las Vegas (LAS) to Houston Hobby (HOU) 1:15 AM Phoenix (PHX) to Nashville (BNA) 1:10 AM Overnight departures are common on eastbound Hawaii routes to the mainland, with a Beat of Hawaii analysis finding more than 55% of Honolulu departures are scheduled between 6:00 PM and 2:00 AM. Conversely, overnight flights from the mainland to Hawaii are comparatively rare. Part of the reason westbound red-eyes remain unusual is that overnight flying is more favorable when traveling eastbound, due to time-zone changes. For Southwest, the schedule works out well from an operational perspective — rather than parking a Boeing 737 in Honolulu overnight, the aircraft can turn around shortly after its 6:10 AM arrival and operate a morning service back to the mainland, allowing Southwest to maximize its aircraft utilization. The Rest Of Southwest's Spring 2027 Expansion Credit: Southwest Airlines In its latest schedule release for next spring, Southwest added more than a dozen new routes, each set to launch in March 2027. Much of the expansion is built around the carrier's focus cities, including Austin-Bergstrom International Airport (AUS) and Orlando International Airport (MCO), as well as boosting capacity from Nashville and Las Vegas. Southwest is also adding to its capacity in Honolulu, boosting its routes to both Hollywood Burbank Airport (BUR) and Ontario International Airport (ONT) up to five times per week. Simple Flying took a closer look at the full spring 2027 route announcement when it was unveiled last week.