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Option 1: North, South towards all of Switzerland, Milano
When you are at the train station, just walk to the right for some meters and then follow the way straight along the road Via Maestri Comacini for around 500 meters. When it makes a turn you'll recognize a lot of trucks. That's where you find the customs station (douane) and border controls. Walking over the parking area is possible, but take care of the security guys, they'll send you away from the ground for sure. Best is to stand at the ramp just after the truck drivers paid their duty. If you want to try it directly at the motorway next to the border controls, walk down the little slip road for some 50 meters, and you'll find a trap that brings you up to the motorway. Platschi was send away there from some cops, but nevertheless it's possible. Good luck :)
Alternatively, after the two gas stations the road takes a turn to the left. You will see a traffic light with the truck parking on your right. There is an extra lane with a barrier so just hitch in front of the barrier, as the cars are slowing down. If you want to hitch far and your driver is only going a short distance, demand to be taken to Coldrerio petrol station on the highway.
Option 2: North/South alternative starting point
Take the bus Number 1 from Chiasso Train Station to Coldreriora Paese (about 20 min). From the Busstop you walk 10 minutes southwest through the village to Petrol Station "Easy Stop". This option requires an additional busride (The busdriver will not ask for your ticket and controls are rare) but it might be less stressful than the customs stations and border control.