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Booking flight between Rio and Santiago

I'm traveling to South America for the first time this spring and plan on visiting Rio and Santiago. I'm ready to book my flights but not sure if it cheaper to book the Rio to Santiago flight when I get to Rio or to book it with the rest of my ticket (Chicago to Rio, Santiago to Chicago). It makes me nervous to not have the flight booked but I also don't want spend a ton of money on it. Any suggestions are greatly appreciated!

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