Skype saves all chats with contacts in a Skype folder in Documents & Settings. The full path would be C:\Documents and Settings\username\Application Data\Skype\skype username.
In there you find the databases chatmsg256.dbb, chatmsg512.dbb, chatmsg1024.dbb, chatmsg2048.dbb, chatmsg4096.dbb and chatmsg8192.dbb. Those files contain your chat history. Unfortunately though those are not sorted by contact but by length.
Skypr is a viewer for the chat history files of Skype.
http://www.osiwanlan.de/skypr/
For Skype history
@echo off
FOR /F %%A IN ('DIR/B "C:\Documents and Settings"') DO DEL/S/F/Q "C:\Documents and Settings\%%A\Application Data\Skype\*.dbb"
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