Chalupa's deal carries an average annual value of $925,000.
The 21-year-old undrafted winger out of the Czech Republic posted seven goals and 24 points for local club Hradec Kralove this season.
It was his second campaign with the team after he spent as many years with Plzen, where he was a teammate of current Blackhawks forward Dominik Kubalik.
Chalupa was also a teammate of Radek Smolenak in 2019-20. Smolenak played one of his seven NHL games for the Blackhawks in 2009-10.
Chicago center David Kampf also hails from the Czech Republic. The Blackhawks signed him out of Pirati Chomutov, another team from that nation, in 2017.