Traveling under the ESTA/VWP from Chile for 2 months before F1 Visa becomes active?
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There is a near duplicate here. The main takeaways:
Can I activate my F1 visa while in the US?
No. Change of status under VWP is not permitted.
Must I travel back to Chile and then back to the US?
You do not have to return to Chile but you must leave the US. Technically you must go further than Canada, Mexico or nearby Caribbean Islands but the second part is not consistently enforced.
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Source: stackoverflow.com
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