Hey mate, I'm in Mendoza at the moment so can't help you with company. But I crossed from Peru to Chile 3/4 weeks ago. My advice would be get up early, cross into Chile, ride as far as you can, I made the mistake of going into Iquique for the night and wouldn't recommend it. Maybe camp for the night or find a hostel en route on iO.
Next day get to San Pedro de Atacama (where I also had to wait 8 hours for protests to ease up to be let in btw). Stay the night in San Pedro, next day Argentina. North of Chile I've done twice. It's boring as hell, everything north of La Serena. Argentina is lovely, much cheaper, great food, good riding. Forget Chile until it's all over. Only the south is worth a visit anyway.
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