Hi, I searched but couldn't find a recent relevant answer.

Would we have any issues if we were to fly into Chicago and then drive up to Canada across the border. Flights for the dates we need are alot cheaper if we book a return from Chicago, even enough to justify the drive there.

I just have a feeling the US border guards wont like us flying back into Chicago as I doubt they would take our word that we will be driving back across the border or am I too skeptical?

Has anyone done this?

There has been a similar thread recently about flying into US on ESTA and driving into Canada. Hope that link works http://britishexpats.com/forum/showt...highlight=ESTA if not go on the Canada main forum and search for "Flying to US on ESTA, driving home to Canada"

Thanks, must not have used the exact word order needed. So we should be ok then as we have work permits

As long as the work permits have been issued and you are currently living here then you should be ok. Their country they decide to let you in or not.
Are you renting a vehicle or is it your own?
If a rental some companies wont allow for drop off in Canada.

we'd be driving our own car down.

Hopefully some flight prices will drop and we can afford the flights from Canada instead