The association between the Air Training Corps and the City of Wollongong extends as far back as World War II, when No 2 Flight of No 28 Squadron paraded in the city as part of No 2 Wing Air Training Corps.

No 2 Wing Air Training Corps was renamed New South Wales Squadron on 19 Nov 45, and the current  No 314 Squadron was reformed as No 14 Flight NSWAIRTC in Armidale in 1951, then transferred to Belmont in 1954. In 1961, under the command of Flt Lt R. 'Dick' Handel, the flight was relocated to Fort Drummond in Mt St Thomas, a suburb of Wollongong. The site on which the flight paraded had been acquired from the Royal Australian Army Artillery, which had used it since 1942 to house personnel manning a coastal battery comprised of two 9.2 inch Mark X guns in defence of Wollongong's local industry against possible sea based attack.

SQNLDR(AIRTC) Jock Kennedy assumed command of the flight prior to the enrolment of the first cadets and the official opening by the mayor of Wollongong, Alderman Squires, on 28 Sep 63. With the retirement of SQNLDR(AIRTC) Kennedy from AIRTC duties in Dec 83, FLTLT(AIRTC) Len Parsons was appointed Flight Commander until his passing in Jul 86, with FLTLT(AIRTC) Arthur Raymond, RFD commanding the flight until his retirement on 10 Dec 91 when FLTLT(AIRTC) Michael Ryan was appointed as Flight Commander.

In 1987, Wollongong City Council approved the use of the city crest on the No 14 Flight banner and the incorporation of the words 'City of Wollongong' in the flight name.

After parading at the Fort Drummond site for 37 years, No 14 (City of Wollongong) Flight was relocated to Lake Illawarra Cadet Facility, on the northern foreshore of Lake Illawarra. The new building was opened on 27 Feb 99 by Senator the Hon Helen Coonan, Senator for New South Wales, who described it as 'a dedicated, purpose built, training facility to benefit both Navy and Air Force Cadets' and a 'major milestone in the evolution of the cadet movement in New South Wales and a visible demonstration of this government's commitment to the Australian Services Cadet Scheme'.

In 2001 the Australian Services Cadet Scheme underwent a review and was subsequently renamed the Australian Defence Force Cadets. The Air Training Corp was renamed the Australian Air Force Cadets and No 14 Flight became No 314 (City of Wollongong) Squadron, with FLTLT(AAFC) Ryan continuing as Commanding Officer. PLTOFF(AAFC) Paul Barrett was appointed Commanding Officer on 01 Jan 12. FLTLT(AAFC) Paul Adams was appointed Commanding Officer on 01 Feb 18.

With an establishment of fifty cadets, 314 Squadron aims to meet the training objectives of the Australian Air Force Cadets by providing opportunities for cadets to participate in all Wing training activities, including flying, gliding, rifle shooting and promotion training courses.