Cheapest cities to fly in to.

Frankfurt out of Chicago.

Keep an eye on Kayak.com, because it varies a bit. Dublin is cheap to fly to right now, but that doesn't put you in one of the countries you mention.

Good luck!

Not sure if it would be the same for flights from Chicago, but when going to Italy from Philadelphia it's almost always less expensive to fly into Milan or Venice rather than Rome. Agree with Matti that Frankfurt is a good possibility for lower fares, as it's a major European hub.

I don't think there is a blanket answer to this question. Obviously more popular destinations like Rome will have higher demand with less pressure for low fare. Recently it was $200/person cheaper for us to fly into Rome and home from Zurich rather than RT to and from Rome. I think you have try them all.

Here's Kayak's lowest fares to Europe, roundrip from Chicago. If you are traveling in Feb, Frankfurt is dirt cheap!

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Fare Alerts: Below are best round-trip fares found since Tuesday, January 13, 2009.

Chicago (ORD) to "Kayak Top 25" (Europe)

Best Fare ORD to Travel Dates

$491+ London (LHR) Jan 27 - Feb 10 search
$491+ London (LON) Jan 21 - 26 search
$645+ Paris, France (CDG) Jan 19 - 26 search
$428+ Dublin, Ireland (DUB) Mar 5 - 12 search
$329+ Frankfurt, Germany (FRA) Feb 3 - 17 search

See all fares Edit this alert delete

For years Frankfurt has been used by experienced travelers because of low over-all expenses.

Research google to see what you can learn. German tax has been cheapest on auto rentals. Petrol will vary from one country to another.

One determining factor for me would be where I plan to travel in Europe. When you choose a destination city
consider where you will spend most of your time.

the obvious places to check are orbitz & expedia. Another place I've found useful is airfarewatchdog.com

http://www.holidays-info.com/School-Holidays-Germany/2009/school-holidays_2009.html

If you use this calendar, it will show you the various school vacations for each state. Germany has rotating vacations, so Munich may be on summer vacation, while Frankfurt isn't. This will make flying into Frankfurt cheaper, and vice-versa. This includes Easter vacations, fall vacations, & Christmas vacations. They will all be slightly different and they change every year. You can seriously save money by utilizing this knowledge in finding your arrival and departure airports.

Joshua,

This is a great resource. Thank you!!

Thank you all. I am not sure how soon I will be able to travel, but this has been very helpful nonetheless.

London doesn't look so bad either, flights around $600 and the pound at 1.45 compared to 2.05 last year...