Visiting the US and Canada

[dayslikethese1]

OK so I am starting from place of complete ignorance so bear with me, hoping someone has done something similar and can advise:

I have always wanted to visit the US and I also have a relative in Toronto, Canada. I am loosely thinking of visiting Chicago next year and then flying into Toronto from there and then back to UK from Toronto.

It looks like you can't buy one way to Chicago without it being hideously expensive (but you can get one way back from Toronto weirdly).....my question is can we do this (get both ways to Chicago and flight back from Toronto) or will it cause a problem with airport security when we get to Chicago? I've been told they ask you all sorts of questions and also that we need both ESTA and eTA VISAs as we're visiting both countries. So can we explain that we're flying back from Canada or will they think that's dodgy or something? We'll obviously have all the paperwork etc., I just don't know how much of an issue that will be.

Also, does that plan sound feasible in general? I really have no idea; I'm just trying to work it all out at the mo. But if we're flying all that way and getting time off etc. I would like to visit Canada at the same time if we can.

Should add that I've never been outside Europe so have no idea about VISAs really or any of that,

The routing I would do is London to Toronto return and then in between book a return flight between Toronto and Chicago. That would be far easier.

You will need both an ESTA and an eTA for Canada if you are a British Citizen. Only use the official US and Canadian government websites for these visa applications as there are plenty of companies who will charge far more for a service you can apply for yourself. The Canadian government charge $7 CA per application and the US government charge $14 US per application.

You could do an open-jaw into Chicago back from Toronto and a one-way sector fare between. Traveling to the US under the VWP (visa waiver program) requires you to have proof of onward travel out of the USA within 90 days of your arrival or you won’t even be allowed on the plane in the UK. It’s big a visa that you need for the US (unless you have ever been arrested) - you will be traveling under the VWP for which you need an ESTA (online pre-authorization to travel without a visa).

It’s not a visa, I mean...