91 days in the US

If the Border Officer notices the date of return, a simple explanation of what you are planning to do is all that is needed.

I don't know how strict they are in practice. My guess would be that if you explain to them that you intend to stay 91 straight days (i.e. one more than allowed), they would have no choice but to deny you entry since you are essentially saying "I am going to break the rules, please let me in". If you on the other hand explain to them that you intend to go to Italy but just haven't bought the tickets yet because you don't know the exact dates, I believe you have a very good chance to enter, since a return ticket is not required to apply for entry (contrary to what some posters claim here). Nevertheless, the airline could decide to not let you board without a return/onward ticket within 90 days, in which case it doesn't matter how lenient immigration is.

If he applied for his VWP online, he had to have entered the dates. If they accepted it, not rejected it, then it is moot. LOL

You don't apply for a VW online. Perhaps you are referring to ESTA, but you don't enter any dates for that. I don't really know what you are referring to.

Perhaps you are referring to ESTA, but you don't enter any dates for that. I don't really know what you are referring to.

In fact you do Max ... the online form for the ESTA does ask us furriners for dates and address while in the US. I entered roughly close dates, plus our first motel in Los Angeles, and the ESTA was approved for a further two years.

Hmm, I am looking at the form right now, and I don't see it. The only dates asked for is birth date, passport issuance and passport expiry. The travel information section (which is not mandatory and can be left blank) includes the city you'll fly out from, the airline and flight number but no dates as far as I can see.

Sometimes I have bouts of RA (Reverse Alzheimer's) - remembering things distinctly, even if they didn't happen!

As I said, I do not personally need to deal with I-94 forms or ESTA as a Canadian. So I am not current on what is or is not included on either the paper I-94 or the online ESTA.

So I had a look. As I now understand it, if you have your ESTA approved you enter without having to fill in an I-94 and just get your passport stamped on entry. Dates of travel are not required as you say Max to get an ESTA approved. The ESTA allows travel for within 2 years after it is approved. So far so good.

So obviously, the question of your length of stay is not going to come up until you get to the Immigration agent at the airport in the US. So he asks, where are you staying (at least first night address required) and for how long. The OP says, '90 days but I plan to leave and return in the middle of that time.' Probably he will be asked to elaborate on that answer and does so. Passport stamped, 'next please'.

I just don't see any big problem here. The OP could even feign ignorance that his dates constitute 91 days. 'NINETY ONE, really? Oh, is that a problem? I will be going to Italy for a few days in the middle. Does that make a difference?'

So obviously, the question of your length of stay is not going to come up until you get to the Immigration agent at the airport in the US.

Read my posts in more detail. There is a considerable risk that the airline will notice it during check-in at the airport. They don't even have to count days; they may ask for return ticket, enter it in their computer, and the system might come back and say that it's invalid. When this happens, the OP may have the option of canceling his trip or buying a valid return/onward ticket. I'm not saying this is what definitely will happen. As I said before, I know of people who travel on one-way tickets to the US without issues. But I've also heard of people who are denied boarding. If it were me, this is what I would be most concerned about, not immigration.

So he asks, where are you staying (at least first night address required)

First night address is not required. I have entered saying I will sleep on the airport floor or in a rental car. But if your admissibility is at question, of course the more you have planned the better.

The OP says, '90 days but I plan to leave and return in the middle of that time.' Probably he will be asked to elaborate on that answer and does so. Passport stamped, 'next please'.

Yep, agreed. If everything else is in order and he convinces the inspecting officer that his trip complies with the VWP and he will return to his home country at the end of it, I think he will be fine.

The OP could even feign ignorance

Now you are advocating lying to the CBP and violating US immigration laws, since we know that he already knows it's a problem.

"I have entered saying I will sleep on the airport floor"

Then you have been asked and answered as required.

When I arrived in the US, the officer wanted to see if I had return tickets or not.

All I had to show was a printed itinerary stating the return dates.
Connect the dots. :)

Once you arrive, rebook your return tickets.
You don't wanna mess with the US gov if you plan on visiting here in the future.

And max's idea of waiting a day in the airport is smart!
Haha

Airline's often cite, 'proof of onward/return travel' as a reason for denying boarding unless you buy a return ticket. Many people believe the airlines when told this. However, if you actually look at the Immigration website for many a country, what you find is that there is no actual requirement for a return or onward ticket. Often what it does say is something like, 'satisfy the Immigration officer that you do not intend to stay or work in the country'.

That 'satisfy' is taken to mean a ticket will 'satisfy' the agent. Which is obviously ridiculous since it may or may not satisfy the agent. Having a ticke is only PROOF that you have a ticket, it does not prove you intend to use it !

So the issue is not necessarily an Immigration requirement, it is an AIRLINE requirement that they try to tell you is an Immigration requirement.

So the issue is not necessarily an Immigration requirement, it is an AIRLINE requirement that they try to tell you is an Immigration requirement.

No, it's an Immigration requirement:
>(c) Restrictions on manner of arrival—(1) Applicants arriving by air and sea. Applicants must arrive on a carrier that is signatory to a Visa Waiver Pilot Program Agreement and at the time of arrival must have a round trip ticket that will transport the traveler out of the United States to any other foreign port or place as long as the trip does not terminate in contiguous territory or an adjacent island; except that the round trip ticket may transport the traveler to contiguous territory or an adjacent island, if the traveler is a resident of the country of destination.

(emphasis added)

The reasons airlines ask is because they are tasked with enforcement:
>(b) Procedures at ports of embarkation. At each port of embarkation carriers shall take reasonable steps to prevent the boarding of improperly documented aliens destined to the United States by taking the following steps:

(1) Screening of passengers by carrier personnel prior to boarding and examination of their travel documents to ensure that:

(i) The passport or travel document presented is not expired and is valid for entry into the United States;

(ii) The passenger is the rightful holder; and

(iii) If the passenger requires a visa, the visa is valid for the holder and any other accompanying passengers named in the passport.

(2) Refusing to board any passenger determined to be improperly documented. Failure to refuse boarding when advised to do so by a Service or Consular Officer may be considered by the Service as a factor in its evaluation of applications under §273.5.