Chris is a long haul trucker who surfs for free Wi-Fi wherever he can find it. Is there a system that will help him find WiFi signals? Leo says not really. Wi-Fi is really designed for a range of about 300 feet. That's why the 3G/4G access is so sophisticated. It has to do with handing off from one area to another.
Free is fairly tricky as well. There is a free service called FreedomPop, but it's not everywhere, and it's ad supported. It's 4G, and he would need to buy a special connector to pick up the signal. It may be worth a look though.
PadreSJ in the chatroom says that he has Freedom pop and they charge him $3.50 for half a gig. Not a bad deal for checking emails on the road.