I-Jet Caribbean has a long and storied history, beginning in the early 1990s. Founded by a group of aviation enthusiasts and entrepreneurs, the airline quickly grew to become a major player in the Caribbean aviation market.

I-Jet Caribbean was originally founded in 1992, with a single aircraft—a Boeing 707. Within a few years, the airline had grown to a fleet of five aircraft, including a mix of Boeing 707s and 727s. The airline quickly became one of the largest carriers in the Caribbean, offering flights to a variety of popular destinations throughout the region.

Throughout the 1990s, I-Jet Caribbean continued to expand its fleet and routes. In 1998, the airline took delivery of its first Airbus A320, which allowed the airline to increase its capacity and reach even more destinations. The following year, the airline added three more Airbus A320s to its fleet.

In 2003, I-Jet Caribbean underwent a major restructuring, which included the addition of 10 new Airbus A320s and the retirement of its aging Boeing 707s and 727s. This move allowed the airline to expand its routes and offer more direct flights to destinations throughout the Caribbean.

In 2006, I-Jet Caribbean suffered a major setback when one of its aircraft crashed on approach to an airport in the Dominican Republic. The crash killed all 166 people onboard, and the investigation revealed that the accident was caused by pilot error. Following the accident, the airline tightened its safety protocols and procedures, and began an extensive series of upgrades and improvements to its fleet, which included the addition of new aircraft and the retirement of older, less reliable models.

In 2007, I-Jet Caribbean launched its first international route, from its base in Santo Domingo to Miami. The airline continued to expand its international network over the following years, adding routes to the United States and Europe.

In 2011, I-Jet Caribbean underwent another major restructuring, which included the addition of 11 new Airbus A320s and the retirement of its aging Boeing 707s and 727s. This move allowed the airline to increase its capacity and offer new direct flights to more destinations.

In 2013, I-Jet Caribbean became the first Caribbean airline to launch a frequent flyer program, which allowed passengers to earn rewards and discounts on future flights. The following year, the airline launched a new low-cost subsidiary, I-Jet Express, which allowed the airline to better compete with low-cost carriers in the region.

Today, I-Jet Caribbean is one of the largest airlines in the Caribbean, with a fleet of 28 aircraft and a network of more than 50 destinations throughout the Caribbean, the United States, and Europe. The airline has come a long way since its humble beginnings in the early 1990s, and continues to expand and improve as it strives to be the premier airline in the Caribbean.