D'Aiello started his career at Palermo. In mid-2005 D'Aiello left for Olbia with option to purchase half of the rights for €20,000. In July 2006 Palermo excised the buy-back option for €35,000 (made Olbia received €15,000 in net from Palermo) and re-sold to Gela in co-ownership deal along with Antonino Di Franco for a peppercorn fee of €500 each.
In June 2007 Palermo gave up D'Aiello and Di Franco for free. After 3½ seasons in Lega Pro divisions, in January 2010 D'Aiello left for Serie B club Torino. On 31 August 2010 he was signed by another Serie B club Triestina in another co-ownership deal.
After the club relegated, he was signed by second division club AlbinoLeffe on 31 August 2011.