The airport is named after British Royal Air Force (RAF) Wing Commander Owen Roberts, a pioneer of commercial aviation in the country, and is one of the two entrance ports to the Cayman Islands.

The upgraded Owen Roberts International Airport passenger terminal no longer has an outdoor observation "waving gallery".

The Grand Cayman non-directional beacon (Ident: ZIY) is located 1.1 nautical miles (2.0 km) short of the approach threshold of Runway 08.

By 1950, Roberts had established regular service between Grand Cayman and Tampa, Florida; Kingston, Jamaica; and British Honduras (now Belize).

Owen Roberts had acquired two used Lockheed Lodestar twin-prop airliners purchased to keep up with the competition whose interest was now piqued by the soon-to-be completed airfield at George Town.

The expansion work began in 2015 with a temporarily extended departure hall being added to accommodate passenger traffic while the tendering process is completed and construction commenced.

On 9 March 2015, the Florida-based company RS&H, which is partnered with the Cayman Island Airport Authority, unveiled a new design for Owen Roberts International.

On 23 June 2015, it was confirmed by CIAA CEO Albert Anderson that construction work would start in early August 2015 and is estimated to be finished in generally 2 years.

Part of the phase 2 reconstruction was the removal of the famous and only A-frame open-air observation "waving gallery" in the region as it was closed to the public in January 2017.

[18] Cayman Airways began nonstop flights to Houston via Intercontinental Airport in the late 1970s and by 1982 had replaced its BAC One-Eleven twin jets with Boeing 727-200 jetliners.

Cayman Airways Express is to eventually retire both of its DHC 6-300 Twin Otters and was also planning to add another Saab 340B to its fleet.

Cayman Airways Express was also planning to expand on short haul regional flights but has not yet announced any new schedules.

[23] Grand Cayman was being served with scheduled passenger flights by the early 1950s when British West Indian Airways (BWIA, which is now Caribbean Airlines) in association with British Overseas Airways Corporation (BOAC, which is now British Airways) was operating one round trip flight a week on a routing of Kingston, Jamaica - Grand Cayman - Belize City with a Vickers Viking twin-prop aircraft with this service being timed to connect to other BOAC and BWIA flights in Kingston.

[25] By 1957, BWIA in association with BOAC had added Montego Bay, Jamaica as a stop on their Kingston-Belize City route flown weekly via Grand Cayman.

[27] By 1963, British West Indian was operating daily Viscount propjet service into the airport with a round trip routing of Miami (MIA)-Grand Cayman (GCM)-Montego Bay (MBJ)-Kingston (KIN)-San Juan (SJU)-Antigua (ANU)-Barbados (BGI)-Port of Spain, Trinidad (POS).

[28] In 1964, LACSA was operating Douglas DC-6B propliner flights on a routing of San Jose, Costa Rica - Grand Cayman - Miami with round trip service twice weekly.

[32] LACSA continued to serve Grand Cayman through the late 1970s with nonstop flights to Miami operated with stretched BAC One-Eleven series 500 jets.

[34] Another international airline flying from the airport was Faucett Perú which in 1985 was operating Douglas DC-8 jetliners between Lima, Peru and Miami three days a week via an intermediate stop in Grand Cayman.

[37] By 1994, Air Jamaica was operating Boeing 727-200 jet service on a routing of Montego Bay - Kingston - Grand Cayman three days a week while Trans-Jamaican Airlines (which subsequently became Air Jamaica Express) was flying ATR 42 propjets on a routing of Montego Bay - Kingston - Grand Cayman - Belize City - Cancún, Mexico twice a week.

In 1987, Northwest was flying McDonnell Douglas DC-9-30 jets from the airport to Miami, Memphis, Tennessee and Montego Bay, Jamaica with daily nonstop service to all three destinations.

[42] U.S.-based regional air carriers Red Carpet Airlines and successor AeroSun International operated service between the airport and Tampa (TPA) with Convair 440 prop aircraft with up to six flights a week during the early 1980s.

[48] Locally based air carrier Cayman Airways was also continuing to fly nonstop service with Boeing 737-400 jets on its core Grand Cayman-Miami route at this time in the face of considerable competition posed by these four U.S.-based airlines with all five airlines operating a combined total of sixty (60) departures a week from the airport to Miami in December 1989.

[50][51] British Airways continues to serve Grand Cayman at the present time with direct Boeing 777-200 wide body flights from London Heathrow Airport via a stop in Nassau.