The currently fare-free system comprises two routes across 2.5 miles (4.0 km) of track, serving eight stations, and crosses the St. Johns River on the Acosta Bridge.

The Skyway connects to the JTA's bus rapid transit system, known as the First Coast Flyer, at the Jacksonville Regional Transportation Center at LaVilla.

In 1976, the city incorporated the system into its mobility plan, hoping to attract interest from the Urban Mass Transit Administration's Downtown Peoplemover Program.

Early proposals recommended a comprehensive system over 4 miles (6.4 km) long that would connect into adjacent neighborhoods, but the project's route and scope were greatly reduced over the years to meet budget constraints and UMTA's parameters.

Subsequent extensions were planned to take the Skyway north to Florida Community College at Jacksonville (FCCJ), and then south across the St. Johns River over the Acosta Bridge.

In October 1994 Bombardier Transportation was awarded a new contract to revamp the existing east–west segment with new technology and to complete the remaining Phase I extensions.

[4][5] The system was shut down on December 15, 1996, to replace the former Matra technology with Bombardier equipment; the older cars were sold to O'Hare International Airport in Chicago.

Ridership in 2013 averaged nearly 4,000 on weekdays (the system is closed on weekends except for special events) and JTA renewed the fare-free policy through the end of 2016.

[9] In light of this momentum, JTA Director Nat Ford has announced the agency will apply for grants to expand the system with a new station in the fast-growing Brooklyn neighborhood.

[12] The review considered options to refurbish the current rolling stock, buy replacement vehicles, expand the system, tear down the structure or convert it to alternative use such as a walking path.

In 2019 the JTA indicated an interim phase would involve the modification of one of the monorail beams to allow use by autonomous vehicles while the Skyway continues to run on the other side.