With its head office in Grand Cayman,[3] it operates mainly as an international and domestic scheduled passenger carrier, with cargo services available on most routes.

A few months after it was formed, the airline flew its first international route to Kingston, Jamaica, operating five times a week using a BAC One-Eleven twin jet wet-leased from LACSA.

[5] The airline was also offering direct connecting jet service between Miami and Kingston via Grand Cayman at this time.

[5] In 1979, an additional BAC One-Eleven jet, as well as a Hawker Siddeley 748 turboprop and a Britten-Norman Trislander prop aircraft were purchased and added to the fleet.

During the 1980s, Cayman Airways offered scheduled or charter service to Atlanta, Baltimore, Boston, Chicago, Detroit, Houston, Minneapolis, Newark, New York City, Philadelphia and St. Louis as well as Kingston and Montego Bay in Jamaica.

On Monday 27 August 2018, Cayman Airways announced in a press conference that the airline was adding Denver, Colorado (DEN) to its list of gateways.

may be served in the future with the new 737 MAX 8 with other possible destinations under consideration including London, England (via a stop in Bermuda) and Brazil.

The second 737 MAX 8 aircraft for the airline was on the assembly line at Boeing Renton Factory late January early February.

Shortly after the first test flight of the airline's first 737 MAX 8, Cayman Airways issued a statement about the safety of the new aircraft and its acceptance into the airline after concerns loomed due to a crash of an aircraft of the same model operated by Lion Air in Asia (Lion Air Flight 610).

In the airline statement, Cayman Airways CEO and president Fabian Whorms stated "I can give a full assurance that our new aircraft will not be delivered or accepted unless it has thoroughly passed all required post-production flight and ground tests successfully.

Once the new aircraft enters service, it will be operated and maintained to the highest standards, with our usual and unwavering commitment to safety.

In the airline statement Cayman Airways CEO Fabian Whorms stated: "We have taken the decision to suspend operations of both our new Boeing 737 Max 8 aircraft, effective from Monday 11 March 2019, until more information is received."

In Late January 2021, The Civil Aviation Authority of the Cayman Islands (CAACI) rescinded its airspace restriction for the 737 MAX 8 aircraft.

Officials explained that the decision follows the approval of extensive modifications to the design of the aircraft, to how it is flown, and to pilot training.

This includes modifications to the aircraft's Maneuvering Characteristics Augmentation System (MCAS), as well as other key safety changes aimed at preventing further accidents.

[13] In Early February 2021, the Cayman Islands Pilots Association (CAPA) issued a statement regarding the reentry of the 737 MAX 8 aircraft.

[14] During the week of the 10 February Cayman Airways Press Conference, Cayman Airways announce public viewing and walkthrough of the newly upgraded 737 MAX 8 aircraft and watch some of the operational test flights at Owen Roberts International Airport and Charles Kirkconnell International Airport over the weekend.

That original design was used on baggage stickers by Cayman Islands Customs and also became the logo of the Department of Tourism which was then headed by Eric Bergstrom.

Wilbur Thompson, the Chief Pilot of Cayman Airways at the time, and the modified Sir Turtle became the airline's new logo.

The Cayman Islands government purchased Sammy's Airport Inn for $2.85 million United States dollars.