Economic well-being within a society will ultimately depend on the productivity increases that occur at industry level. Digitalization and the use of ICT are tools of capital importance in this process. However, in order to scale up to industry level, they should first appear at an individual level. Having or not having ICT skills will therefore be crucial both for the individual (not to be left behind due to his/her digital divide) and the society (to keep up with the economic development of other regions). In this research we study the existing relationship between ICT skills and the free market orientation, both in its political and economic component. We find that ICT skills is a complex measure, that can interact with free market in some aspects and be independent in others. The use of on-line banking, communication technologies and the access to databases are not linked to free market orientation. But the ability to buy on-line is found to be positively correlated with free market orientation, which could speak of the existence of trust in the markets as a facilitator of on-line purchasing. Contrarily, on-line selling is negatively correlated with free market orientation.