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If I have a valid US visa and a Canadian PR, can I drive into the US, and then fly out of and into the country and then drive back to Canada upon arrival to get around the (usually) high Canadian airfares?

Are there any gotchas or issues I need to be aware of?

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Absolutely you can. Canadians do this all the time. Driving to Buffalo airport (or Detroit or Seattle) and then flying to the Caribbean for a week is a time honoured part of Canadian culture, and with a valid US Visa you can join in too.

Parking is no more of a problem at US airports than Canadian ones, and often less. You need to leave plenty of time to cross the border if you try it at a peak time.

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    We do it often from Montreal too as flying out from Burlington often saves hundreds per passenger. For a family, it is definitely worth, plus long term secure parking is quite affordable there. – Itai Jun 30 '17 at 1:28
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While you could certainly do this without any Visa implications - the challenges you will have are around:

  • storing your vehicle
  • sunk capital cost of vehicle
  • cost of Fuel & Vehicle maintenance
  • Your time

In short, there is an economic reason why plane travel continues to grow. It does make economic sense.

I have not looked into it - but possibly if there is a train that goes between your cities that would be a viable alternative to the idea of using a car the way you describe? And if you do your comparative sums carefully - you may be able to create a positive arbitrage.

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    A bus would be preferable to the train. There are only three trans-border trains, and while scenic, they are not the speediest: the Adirondack takes 10½ hours to get from Montreal to New York, and the Maple Leaf takes 13½ hours to get from Toronto to New York, and there is only one of each per day. The Cascades is a little better, but I would still recommend the bus for anyone whose priority is the destination rather than the journey. – choster Jun 30 '17 at 0:08
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    -1 You seem to be almost entirely discussing the cost of car ownership as if the asker was proposing to buy a car specifically for this purpose. They are almost certainly not proposing that: living in north America without a car is rather difficult, not least because of the almost total lack of intercity passenger rail. The cost of car ownership isn't what this question is about. – David Richerby Jun 30 '17 at 10:53
  • @choster You can take Canadian trains to Sarnia (Port Huron), Windsor (Detroit), or Niagara Falls (Niagara Falls). Local transportation to the border crossing, then local transport to the Amtrak or airport. Buffalo has only one train that crosses the border but many more that do not. Or you could go to a downtown Detroit hotel and get a Supershuttle to the airport. – Harper - Reinstate Monica Jul 2 '17 at 2:20
  • @David-Richerby - You are absolutlely right that I wrote this slanted towards buying a car for the purpose. I put the question too much in my own shoes. I was thinking along the lines of - this is a person with a Work visa in Canada - also with a legitimate visa in the USA who wants to fly from their home country to Canada - BUT use the USA as a jumping point to reduce the airfares. The other answers are much more sensible - where this person is living in CA and just wanting to use the USA as a travel stop to another brief holiday destination. – kiltannen Jul 23 '17 at 23:40
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No limitations on what you plan.
The only point to keep in mind is a potential time limit on your visa - if it allows for example 90 days, and you fly to Mexico , the clock continues running. So for example, if you stay 85 in Mexico, you have only 5 days left in the US - before and afterwards together. You don't get another 90 days when you 'only' went to Mexico (or Canada). If your Visa has no such limit, you are fine.

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    Is the visa limitation actually an issue here? The limitation is designed to stop somebody spending, say 90 days in the US, crossing the border to Mexico, then coming back to the US to continue what is really a single stay. Spending a few hours (or even days) in the USA, then spending 90 days in Mexico, then spending another few hours in the USA is a very different situation. – David Richerby Jun 30 '17 at 12:19
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    There is no US visa with a 90-day limit. You're thinking of the visa waiver program. Furthermore, the well known "clock" rules relating to adjacent countries are also part of the VWP. Different rules apply to visa travelers. – phoog Jun 30 '17 at 15:06

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