[7] The airline was established by Clement Melville Keys on 8 October 1929 as Compañía Nacional Cubana de Aviación Curtiss S.A., initially as a flying school as well as a charter carrier, beginning scheduled services in 1930.

Cubana became a founding member of IATA, and participated in the creation of that organization through its involvement with the Havana conference and the resulting accords.

The new route to Europe made Cubana one of the earliest Latin American carriers to establish scheduled transatlantic service.

[22] The airline had expanded earlier that year its scheduled transatlantic services, adding Prague to its European route network that solely included Madrid.

[27][28] With the U.S. breaking relations (in 1961) and the imposition of the U.S. embargo on Cuba (in 1962), Cubana was forced to cancel all its U.S. services and turned to the Soviet Union to obtain new aircraft.

At this time, the airline flew internationally to Barbados, Basel, Berlin, Bissau, Buenos Aires, Georgetown, Kingston, Lima, Luanda, Madrid, Managua, Mexico City, Montreal, Panama City, Paris and Prague; it also served a domestic network consisting of Baracoa, Camagüey, Holguín, Nicaro, Nueva Gerona, Santiago de Cuba and Las Tunas.

[31] In the early 1990s, Cubana pursued a multi-faceted strategy to face the challenges posed by the dissolution of the Socialist bloc and the Soviet Union.

This strategy targeted a restructuring of Cubana's fleet, the revamping of the airline's technical capabilities, and upgrading the quality of passenger services.

Cubana had received its last three new Il-62Ms in late 1990 and early 1991 [along with two other (also new) similar aircraft in 1988 and 1989], and was able to keep them in service long after the Soviet Union's dissolution and the end of all Il-62 production in the mid-1990s.

Cubana started leasing some Western aircraft (Airbus, Boeing) for limited periods of time in the mid-1990s, to help sustain its services to Europe, Canada and some Latin American destinations, given the rapid growth of Cuba's tourism sector.

In the early 2000s, Cubana refurbished several of its Il-62Ms to use on some of its international routes (all but one of these aircraft were removed from service in 2011), and in 2004 it embarked on a long-term renovation programme.

In July 2004, the airline placed an order for two convertible Ilyushin Il-96-300s in a US$110 million deal;[33][34] 85% of that price was financed by a loan from Roseximbank,[35] while Cuba's Aviaimport raised the money for the balance.

[39][40] During the August 2007 MAKS Airshow Cubana signed a memorandum of understanding with Ilyushin Finance Company (IFC) for the purchase of another two Tu-204s and three Antonov An-148s.

[48] As of January 2025, Cubana operates scheduled flights on two domestic routes within Cuba as well as to two international destinations in Venezuela and Spain.

[2] In 2024, Cubana was forced to end further international flights to Argentina, which it had served from both Havana and Cayo Coco, after the airline has been refused further supply of fuel.