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 began his studies under Daniele Crespi as a young pupil before moving to Bologna at an early age to learn from Guido Reni. The stylistic influence of Guido Reni is apparent in Cittadini's early works, including the Stoning of Saint Stephen, the Flagellation, and the Crowning with Thorns at Santo Stefano Church in Bologna. In the mid-1640s, he traveled to Rome where he encountered French and Flemish artists.