In 1927, the airport opened on 640 acres (260 ha) 7 miles (11 km) east of the city, with two gravel runways. For the first ten years several small airlines operated a mail route from Cheyenne, Wyoming, to Pueblo, Colorado, with stops at Denver and Colorado Springs. These airlines only occasionally carried passengers. In 1937, Continental Airlines began service between Denver and El Paso, Texas, with stops at Colorado Springs, Pueblo, Las Vegas, New Mexico, Santa Fe, and Albuquerque. In 1943 Braniff Airways began service on a Denver-Colorado Springs-Pueblo-Amarillo route. At Amarillo, flights would continue onto Dallas and Houston or onto Oklahoma City, Tulsa, Little Rock, and Memphis. The first municipal terminal was built in 1942 in an art deco style. Soon after the terminal was built the field was taken over by the military in the months preceding World War II. After the war, the city regained control.

In 1966, a new terminal was built on the west side of the runways, just east of Powers Boulevard. This terminal expanded by the 1980s, with a six gate addition. By 1991 the airport had three 150-foot (46 m) wide runways, one 13,501 feet (4,115 m) long, making it the longest runway in Colorado until 16R/34L, a 16,000-foot (4,900 m) runway, opened at Denver International Airport in September 2003. In 1991 the city approved a new terminal, two miles east of the former terminal, in the south-center part of the airport. The 280,000-square-foot (26,000 m2) terminal opened on October 22, 1994, with 12 gates; it was designed by the Van Sant Group and cost $140 million. In the 1990s a second, five-gate concourse was added on the east side of the main terminal.

In 1996, the 1941 passenger terminal, two hangars, and a caretaker residence — by that time all located on Peterson Air Force Base — were inscribed on the National Register of Historic Places. They form the campus of the Peterson Air and Space Museum.

From the 1980s to the present day, the airport has tried to expand service. The largest number of passengers was nearly 5 million in 1996 when now-defunct Western Pacific Airlines had a hub at COS (Western Pacific moved the hub to Denver International Airport in late 1996). Their timetable for June 15 shows 33 daily departures to 20 airports between the west coast and Newark and Washington Dulles. Frontier Airlines added and dropped various routes from Colorado Springs throughout the 2010s. Southwest Airlines announced in October 2020 that they would begin serving the airport in 2021. Southwest conducted their first flights in March 2021, which has since bolstered the airport's commercial traffic.

In May 2021, the airport began a pavement rehabilitation project, closing runway 17R/35L for remodeling. The upgrades include new asphalt, lighting, and navigation equipment. The airport announced in November 2021 that the main concourse (gates 1–12) will undergo a $10–$20 million renovation and will be completed in 3 to 5 years. The concourse was completed in 1994 and has not been renovated since then. The design has become outdated, prompting airport officials to renovate. On March 1, officials announced that COS will receive a $6 million grant to complete the planned renovation. Construction will start in the summer of 2023.

In March 2022, the Colorado Springs Airport released a plan to expand the airport, with plans to double the number of gates from 12 to 24, relocate the control tower, and consolidate other airport services.