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Backpacking through Europe in 2012

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Hi all-
I graduate in Dec and am planning a 1.5 month long trip backpacking through Europe with my boyfriend.

My question is this: We do not care where we fly into and where we fly out of. We have a list of countries that we want to see and are planning on taking the eurail around and getting one of their passes. Is there a website where we can be this flexible and choose our departure airport (Chicago- O'Hare) but say "ANYWHERE!" for our destination airport? Every website I have gone to I have to choose one place, but I really do not have a place in mind where we should start (like I said, we are flexible!!). Any ideas?

Or does anyone have tips of how to get the cheapest flight out there? Or cheap cities to fly into?

Thanks

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