Initially a pupil of Daniele Crespi, Cittadini moved to Bologna before the age of 20 to study with Guido Reni, whose influence is clearly evident in such early works as the Stoning of Saint Stephen, the Flagellation and the Crowning with Thorns in the church of Santo Stefano, Bologna. He travelled to Rome in the mid-1640s and came into contact with the French and Flemish artists living there.
Cittadini started his artistic education under Daniele Crespi as a young student before relocating to Bologna to study with Guido Reni. The impact of Guido Reni's style is evident in Cittadini's early works, such as the Stoning of Saint Stephen, the Flagellation, and the Crowning with Thorns at Santo Stefano Church in Bologna. In the mid-1640s, he moved to Rome where he interacted with French and Flemish artists.