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I am currently in NYC and by the time I intend to fly (2nd August), I will have been in the USA for 90 days. My plan is to go to Canada for a few weeks to visit friends and then return to USA for 2 weeks before flying out of NYC to Colombia on the 31st August.

When I booked my flights, I didn't realise that trips to Canada were included in the 90 day visitor visa (esta).

Can I re-enter USA on a new ESTA for 2 weeks if I have proof of my flight to Colombia in two weeks from the date of entry?

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    If you entered with ESTA then you do not have a visa; you are instead using the Visa Waiver Program (VWP). I guess you will be okay with your plan but it's by no means certain. The law is worded in such a way as to give wide discretion to border officers, and we can't predict what they'll do. – phoog Jul 15 '16 at 17:16
  • One more point: ESTA is valid for two years. You won't need a new ESTA. You'll use the same one, and just apply for a new period of admission under the VWP. – phoog Jul 15 '16 at 18:10
  • Related, possibly a dupe: Can you re-enter USA on an ESTA? – mts Jul 15 '16 at 22:10
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Technically yes, but you'll have to convince a probably unfriendly CBP officer that you're genuinely going to leave the US and aren't trying to break the rules. With the short amount of time out of the US, this will be very difficult. With the itinerary you've given, you should expect to be refused entry and stuck in Canada. It would be easier if you were merely transiting and leaving the US on the next flight.

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