A new reboot of the iconic Eastern Air Lines is flying between New York and Cabo this winter for under $250 round-trip

• Eastern Airlines is launching non-stop flights between New York and Los Cabos, Mexico, starting November 14.
• No, not that Eastern Airlines.
• The new airline is a product of 2020 that's attempting a reboot of the iconic Eastern Air Lines that ceased operations in 1991.
• Flights to South America began in January and expanded to the Caribbean over the summer but the new airline is nothing like the old.

Cabo San Lucas, Mexico will only be a non-stop flight away from New York City this fall as a new airline prepares to inaugurate a new route between the two cities on November 14.

Eastern Airlines will operate the twice-weekly flights to the Mexican vacation destination, departing from New York's John F. Kennedy International Airport and currently selling for unusually low introductory fares of under $250 round-trip. But while many will recognize the airline's name, hardly any will recognize the airline itself.

No, it's not the Eastern Air Lines of the 20th century, though this airline is trading on its name and brand. Eastern Air Lines (with a space between air and line) was a major US carrier that ceased operations in 1991 and has been the focus of two relaunch attempts in the past decade alone.

January saw its first flight of the reincarnated airline between New York and Guayaquil, Ecuador, operating the first scheduled passenger flight under the Eastern name in nearly 30 years, but with a completely different look and feel.

A dynamic history

Aviation said goodbye to the original Eastern Air Lines in the early 1990s after a 65-year run that started in 1926 as Pitcairn Aviation. A leader in the domestic market, the magnitude of its loss to US aviation was comparable to that of Pan American World Airways and Trans World Airlines.

The second iteration of Eastern Airlines took flight in 2015 with Boeing 737 aircraft used exclusively for charter operations, according to AirlineGeeks. Planes were painted in the iconic blue and white livery complete with Eastern's original logo but it was largely a novelty as the average flyer couldn't book a flight on the new airline.

Charter aircraft of that size are typically reserved to transport large groups including sports teams, military troops, and even presidential campaigns. The limited nature of its return to the skies meant the public was largely unaware of Eastern's comeback until it was bolstered into the spotlight in October 2016.

The airline was involved in a high-profile incident when one of its planes flying for the Trump campaign and carrying then-Governor and Vice Presidential Candidate Mike Pence overran the runway while landing at New York's LaGuardia Airport. No injuries were reported, according to PBS, but the incident occurred just days before the 2016 election that made Pence vice president.

It wasn't Trump's first run-in with Eastern, as he had bought the Eastern Air Lines Shuttle 26 years prior and turned it into the Trump Shuttle flying between New York, Washington, and Boston. But like the Trump Shuttle, the second coming on Eastern was short-lived, ceasing operations in 2017.

The storied history notwithstanding, the new Eastern Airlines also isn't exactly a new airline. It's the end result of a rebranding effort by Dynamic Airways, a similarly obscure airline that operated similar flights from New York and Florida to the Caribbean and South America.

Unlike the charter airline, this version of Eastern kept the name but introduced a new branding style and livery for its aircraft. The only identifiable remnants of the old airline on the newly-repainted aircraft is a small former Eastern Air Lines logo on their tails.

New flights from New York

Eastern's relaunch centers around a New York and Miami-based route network with an all-international flying schedule. Its first flight departed in January from John F. Kennedy International Airport bound for Guayaquil, Ecuador – a popular route also served by JetBlue Airways and LATAM Airlines – with a second route to Georgetown, Guyana from New York starting in March and third to Port-au-Prince, Haiti in August.

The new route to Los Cabos will be the airline's fourth from New York and sixth overall as Eastern also operates two routes to South America from Miami. Its only competitor on the New York-Los Cabo route will be United Airlines, which flies from nearby Newark, New Jersey also non-stop to the Baja California Sur vacation destination.

Eastern's flights will be operated using Boeing 767-300ER aircraft offering two cabin classes of service, economy and premium. Economy seats are configured in a standard 2-3-2 configuration while the premium cabin will see recliner seats in a 2-2-2 configuration.

The twice-weekly service will depart on Wednesdays and Saturdays from JFK Airport's Terminal 4 at 9:20 a.m. and arrive at Los Cabos International Airport at 1:30 p.m., according to Cirium route data. The return flight departs the same days at 3:30 p.m., arriving back in New York at 11:40 p.m.

Flights on most Eastern routes aren't daily and passengers expecting the Eastern Air Lines of yesteryear will be disappointed. A January inaugural flight review by The Points Guy found that the experience left a lot to be desired, even in the premium cabin.

But the airline does allow free checked bags and only charges $10 for regular seat assignments and $25 for exit row or extra legroom seats. Combined with the low introductory fares on the new route to Mexico, flyers not caring about extras like in-flight entertainment can safe on airfare.

Visit South America, on Eastern Airlines

Eastern has plans to expand further into South America to destinations further below the equator than Guayaquil. Recent filings with the Department of Transportation request authority for the airline to fly to Buenos Aires, Argentina, and Santa Cruz, Bolivia, from Miami.

Bolivia flights would start in November while Buenos Aires flights would begin in December if approved.