The following observations are simply that, observations which stimulate questions; they are not based on detailed art historical research but rather on visible similarities in the works of several masters of the Baroque period.
Did Caravaggio pass through Bologna on his way to Rome? I have no idea; in fact, although I have never read any attempt to retrace that journey, Caravaggio's passage to Rome from Milan - or at least the area of Lombardy, possibly via Venice - may well have taken him, like modern travellers today from either place (Milan or Venice), through Bologna. This question occurred to me while studying and admiring the canvases of Ludovico Carracci, the older cousin of the generally better known brothers Agostino and Annibale Carracci.
My curiosity was pricked by one of Ludovico's paintings in the Pinacoteca Nazionale di Bologna, the Probatica Piscina, a large canvas painted in 1595-96. This picture shows Christ healing a man who is waiting at the Pool of Bethesda (the Probatica Piscina or Sheep's Pool) to be cured by its miraculous waters; on the occasion when an angel descends and stirs the waters of the pool, people who enter in the water could be cured of their physical ailments.
But let's now take a short detour to Milan, where Caravaggio was from, and visit the wonderful museum of the Brera (the Pinacoteca di Brera). Here is a startling picture made in about 1606 by a painter of Pisan origin (therefore Tuscan), Orazio Gentileschi, the father incidentally of the equally important painter, Artemisia Gentileschi.
Orazio is important in his own right but also because he was a friend and early follower, in Rome, of Caravaggio himself. In relation to angels, there is a story that Gentileschi at one point loaned to Caravaggio his studio props of a pair of (eagle's? swan's?) wings and a Franciscan monk's habit so that he could use them in his own paintings. Caravaggio and other painters would attach such real wings to the backs of their 'angelic' models so as to obtain the correct fall of light when painting them.
The photo above shows the Seven Works of Mercy, painted by Caravaggio in Naples in 1606; to note here are the angels supporting the Virgin Mary in the top third of the painting and the reclining male nude in the lower left. The left-hand angel has darkly-feathered (eagle's) wings (difficult to see in the photograph) and open arms, whereas the right-hand one has open white wings, also possibly modelled on the original set loaned to Caravaggio by Orazio Gentileschi. If Caravaggio had been stimulated by these elements in the work of Ludovico Carracci, he has done more with the wings which, in Ludovico's painting, in fact look more like those of a dove, and he has reversed the pose, with other alterations, of the nude figure in Ludovico's picture.
Orazio Gentileschi's painting, made in Rome around 1606-07 (Christiansen, 2025 1), has a marvellously developed angel with splendid open wings and arms, as does Caravaggio's left-hand angel above. However, Orazio, as far as is known, never visited Naples and his Brera painting was painted it seems in the same year as Caravaggio's in the Pio Monte (1606); meaning that Orazio never saw Caravaggio's painted wings in Naples and, vice versa, Caravaggio never saw Orazio's in Rome. If the story about Orazio lending 'his' wings to Caravaggio is true, the similarity in the posing of wings by the two friends, even when many kilometres apart, suggests the use of the same model, viz. the pair of real wings owned by Orazio Gentileschi; the posing of the angel, if not the wings, may originally have been stimulated in Caravaggio, if he had passed through Bologna, by his viewing of Ludovico Carracci's angel in his Probatica Piscina! Importantly, the open-armed gesture of Ludovico's angel is one favoured by Caravaggio and is clearly very significant in Gentileschi's picture.
As already said, the use of descending angels, angels in flight as it were, was a prerogative neither of Ludovico Carracci nor of Caravaggio, and neither was the device of a reclining nude figure in the lower foreground of works of art, a theme dating back to classical times. What stimulated the present observations was the similarity of these elements in the works of these three masters in particular, as well as the (possible) physical proximity - in a broad sense - of each of the painters to one of the others. In the case of Gentileschi and Caravaggio, their friendship is documented fact and, in the case of Ludovico Carracci and Caravaggio, the influence of the older painter, Carracci, on the younger is merely a plausible, hypothetical possibility.
Both Ludovico Carracci and Orazio Gentileschi were older than Caravaggio and both outlived him. Although Caravaggio had mistresses it is unknown whether or not he fathered any children; Ludovico, as mentioned, was the cousin of two famous painters, the brothers Agostino and Annibale Carracci; and Orazio, the son of a painter, was the father of the very famous painter Artemisia Gentileschi; interestingly, she sometimes signed her work Artemisia Lomi, her grandfather's surname - for example, in her presumed portrait of her father of 1639-40: Artimisia [sic] Lomi 2; Orazio used his mother's family name, Gentileschi.
1 Keith Christiansen, essay Il viaggio di Gentileschi oltre Caravaggio in Orazio Gentileschi - Un pittore in viaggio, p 23; catalogue published by Moebius, 2025, edited by Annamaria Bava and Gelsomina Spione, on the occasion of the Gentileschi exhibtion at the Musei Reali di Torino, November 2025 - May 2026
2 Un pittore in viaggio; p 72 Judith W. Mann, essay Orazio Gentileschi: venticinque anni dopo.