Swiss Railways (SBB/CFF/FFS) operates a train from Chiasso to Milan hourly. Tickets cost $8 - $17 and the journey takes 42 minutes. Trenord also services this route hourly. Alternatively, Autolinee Gambioli operates a bus from Chiasso to Milan once a week. Tickets cost $7 - $11 and the journey takes 50 minutes.
Yes, there is a direct train departing from Chiasso and arriving at Milano Centrale. Services depart every 30 minutes, and operate every day. The journey takes approximately 42 minutes.
Yes, there is a direct bus departing from Chiasso - Dogana and arriving at Famagosta. Services depart once a week, and operate Friday. The journey takes approximately 50 minutes.