Am I a repeat traveler in terms of ESTA?
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Yes, you are considered a repeated traveler as long as you have been to the US at least once after 2008. From the Automated Passport Control (APC) Page:
Who Is Eligible to Use APC
U.S. and Canadian passport holders and international visitors from Visa Waiver Program countries are eligible to use APC kiosks. Visa Waiver Program visitors must have Electronic System for Travel Authorizations (ESTA) approval prior to travel and have visited the United States on at least one occasion after 2008.
Upvote:3
It's unfortunate that a semi-official site was using such imprecise language. The confusion between ESTA and the Visa Waiver Program (VWP) is very common among travellers but the Chicago Department of Aviation ought to know better. (Indeed, perhaps they do now, since they no longer use the text quoted in the question.)
VWP is the programme that allows people from various "friendly" countries to make tourist and business visits to the USA without a visa. ESTA is a security check programme that requires VWP visitors to submit information to the US government online before travelling. An ESTA authorization is only valid for two years but can be used for any number of visits within that time.
What they should be talking about is repeat Visa Waiver Program visitors. What matters is whether or not you've entered the USA under the VWP before; it is irrelevant whether this was on your current ESTA or on some previous, expired ESTA. (Nean Der Thal's answer quotes the official documents on this.)
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