Career
2009-2010 season
Caldirola started his career at Internazionale, where he was the team captain at under-20 level (Primavera) and was occasionally called up to join the first team during the 2009-2010 season, without making any appearances, however, on the pitch. Caldirola also played for various youth teams in Lombardy as goalkeeper and midfielder before joined Internazionale at the age of eight. He played in a friendly match for the Inter first team in 2009.
2010-2011 season
On 29 June 2010, Internazionale loaned out Caldirola to Dutch club Vitesse Arnhem of the Eredivisie for the entire 2010-2011 season.
He is the second Italian player to be part of the Arnhem club, after Marco De Marchi. Inter also reduced the age limit of its Primavera team to under-19 in 2010, keeping only three players born in 1991 in the 2010-2011 season as back-ups for the first team
Half of the registration rights of Caldirola — and Luca Garritano — were sold to Cesena as part of the deal that brought defender Yuto Nagatomo to the San Siro in June 2011, after a successful loan. Half of the registration rights of Caldirola was valued €2.5 million.
Caldirola signed a four-year contract.
Both Caldirola and Garritano returned to Internazionale in a temporary deal for the 2011-2012 season. 2011-2012 season
On 7 December 2011, Caldirola made his first team debut for Internazionale in a Union of European Football Associations Champions League Group Stage match against CSKA Moscow. On 4 January 2012, Internazionale confirmed that Caldirola signed a loan deal until the end of the season with the Serie B outfit Brescia.
2012-2013 season
In June 2012, the co-ownership deal was renewed and Caldirola reported to Cesena in pre-season on 10 July 2012, where he played the first half of the season for the Romagna club before again being loaned to Brescia in January 2013, where he finished the campaign with 15 league appearances.
Werder Bremen
On 26 June 2013, SV Werder Bremen confirmed the signing of Luca Caldirola from Internazionale on a four-year contract, for a €2.5 million transfer fee. Upon signing for the Bundesliga club, Caldirola stated: "Werder is a great opportunity for me, I immediately said that I would like to switch to Werder.
The club has a great tradition."
SV Darmstadt 98 (loan)
On 15 July 2015, Caldirola was loaned out for a season to SV Darmstadt 98. Caldirola has represented his native country of Italy at all youth levels, from under-16 to under-20.
On 17 November 2010, he made his debut with the Italy under-21 team in a friendly match against Turkey in a 2–1 victory played in Fermo.
In 2009, he participated at the Union of European Football Associations Under-19 Championship with the Italians. In May 2011, he was called-on by Ciro Ferrara to play the games of the 2011 Toulon Tournament. Under the management of Devis Mangia, in 2012, Caldirola was named captain of the under-21 side, where he led the Azzurini in the 2013 Union of European Football Associations European Under-21 Football Championship.