We flew in to Santiago and were charged a "reciprocity fee" of about US$135 (it was a few dollars more for the Canadian).
There was no charge for our visas (one US citizen, one Canadian citizen). And we entered many times back and forth with Argentina and were never charged any fees at the border. (We did have to give up some food items sometimes.)
I don't know about immigration offices along the way. On motorcycles, zipping over to Argentina is no big deal -- not so for you on bicycles. But it's an option if you can't find immigration offices along your route. Even take little bus trip -- some folks we met in Santiago had come by bus from Mendoza and it only cost about $20.
Sorry I can't help with first hand experience -- we spent several months traveling in and out of Chile but never managed to go more than a month or so without crossing a border.
-Laura
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