What's Old Is New Again as Eastern Returns With Flights to Philly

The latest incarnation of an aviation legend is expanding. Eastern Airlines — no, not Eastern Air Lines — is launching new routes from Philadelphia to Santo Domingo in the Dominica Republic and Port-au-Prince, Haiti. But bewarned, this is not the Eastern Air Lines that many people remember.

The new Eastern is growing, after having moved its headquarters last year to Wayne, Pennsylvania, in the Philadelphia suburbs. The carrier has transformed itself from a charter operator to offering a handful of scheduled routes, mainly to the Caribbean, on a fleet of Boeing 767s.

The operator's charter and cargo experience is standing it in good stead now, when the two healthiest parts of the airline industry are cargo and visiting friends and relatives (VFR) leisure traffic.  “So much of travel right now is visiting friends and relatives," Philadelphia International Airport CEO Chellie Cameron said in a statement. "By offering destinations like Port-Au-Prince and Santo Domingo from Philadelphia, Eastern is making travel more accessible to so many of our neighbors when they are ready to travel.” 

But first, a little history. The new Eastern is the latest in a string of attempts to revive the storied name, one that had an outsize effect on the airline industry that can be felt even to this day. The original Eastern Air Lines traced its history to the earliest days of commercial aviation, and at one point was led by World War I flying ace Eddie Rickenbacker. That airline operated a massive route map throughout the U.S. and abroad, mainly in Latin America and the Caribbean. It was a launch customer for the Lockheed L10-11 (which it branded the "Whisperliner"), which lived on in Delta Air Lines' fleet until the early 2000s.

Eastern pioneered the airline shuttle between New York and Washington, D.C. and Boston, which will be a footnote in presidential history: A young real-estate developer bought the Eastern Shuttle and rebranded it the Trump Shuttle in the 1980s (and it subsequently went out of business in the early 1990s).

Eastern Air Lines ultimately was roiled by labor strife after the relationship between then-owner Frank Lorenzo and unions collapsed. The carrier filed for bankruptcy and ceased operations in 1991.

Since then, several entities have tried to capitalize on the legendary name and revive the airline. Swift Air bought the intellectual property in 2011 and operated a fleet of B737s (in another footnote in presidential history, an Eastern Boeing 737 carrying Vice President Mike Pence, then a candidate, skidded off the runway at LaGuardia during the 2016 presidential campaign). That airline collapsed a year later, and Swift sold the intellectual property to Dynamic Air, which began operating as Eastern Airlines in 2019.

Eastern Airlines now operates a modest network of scheduled flights throughout the Caribbean. In addition to the Boeing 767s, the company has acquired a few Boeing 777s, suggesting that it has ambitions to fly further afield. Perhaps the third time is the charm.