To provide a pressurised twin-engined transport which would serve as a 'step-up' aircraft for owners of light un-pressurised twins, Cessna married the basic fuselage of the Model 421 with the wing developed for the Model 401. The resulting aircraft was designated Cessna Model 414, flown for the first time on 1 November 1968 and certificated during the following August. A number of optional seating layouts for up to seven passengers plus a wide range of cabin appointments were available to customers, and new features introduced on the aircraft included engine cowlings with flush intakes to improve engine cooling and an accurate fuel monitoring system developed by Cessna to provide better fuel management.

From the time of its introduction until 1976, improvements introduced for the Model 402 were reflected in the Model 414, and in that year the name Chancellor was adopted. It was available for 1976 in standard and Model 414 II versions, the latter incorporating a package of factory-installed avionics and equipment. For 1978, after 513 of the original Model 414s had been built, an improved version was introduced as the Model 414A Chancellor, major changes including a redesigned and increased-span wing incorporating integral fuel tanks and more baggage capacity in an extended nose.

Versions available between 1978 and 1986, were the standard Model 414A Chancellor, the Chancellor II an.d later the Chancellor III, all with differing factory installed avionic/equipment packages. When Model 414/414A production ended in 1986 a total of 1,067 variants had been built.