Looks like St. Louis currently, but depends when you want to travel, how long you want to stay, and when you book your ticket.

Here’s a couple sites that you might like:
Skyscanner everywhere over a month search
Farecompare getaway maps with adjustable outbound month

Oh and I forgot that I’m planning to go backpacking to Europe. This is going to be the first time I do this trip so I am starting from scratch doing all the research. I think I came up with Chicago-London being the cheapest. Maybe there is something cheaper?

Maybe. Like I said, it depends on when, how long, and when you book. What’s available right now does not stick around forever. If you bookmark and check Farecompare maps link I made for you, and/or sign up for sale alerts, then you might do better to someplace else. From CHI, I have seen DUB, FRA, CPH, and STO cheapest options in recent months, but LON might be currently. Sounds like you’re flexible enough to make any of these work for you.

A related tip … check out multi-city flights too. CHI>LON, ROM>CHI for example. This could save you backtrack time and expenses. Multi-city flights typically don’t cost much, if any, more than a simple roundtrip. Cfares, Mobissimo, Kayak, and Fly.com are good to check for multi-city. Once you spot a good fare or get an alert, then use these to shop it thoroughly.

That sounds like great advise! I actually did not think about the multi city option! The map is Great also! definitely helps! I don’t plan on traveling until summer 2012 so I know prices will probably be different by that time. I just wanted to start looking and seeing around how much I’m going to need.

One more question, for the train system (eurorail)….

say I buy a five country pass for 5 days. that is five days that don’t have to be consecutive? and that includes travel from country to country and within that same country? e.g.
1Day—Italy-Spain. That same day I use the pass all day in Spain (madrid-barcelona-salamanca)
but now that I asked that I realize that I probably will not be able to cover all that in a single day. What pass is more convenient for a trip like the one mentioned above?

For more flight tips and strategies, be sure to check our new user thread pinned @ top of this forum — especially if you’re a student or under 26, for example.

Re: rail passes, get definitive info from the gurus on our Transport forum next-door on Eurotrip.com. My quick take on it: Pass days are not consecutive, unless you buy a “Consecutive” pass. For example, 5 days in 15 would mean you have unlimited travel on any participating train lines for 5 full days over a 15 day stretch, starting from the first day you use your pass. A 5 consecutive day pass would be just that—use it or lose it within 5 days of first validation (use). Consecutive passes (do they still exist?) aren’t normally useful or recommended for most travelers. I don’t recall the last time (in 15? years) someone posted on our forums about purchasing one. A 5 in 15 would serve the same purpose if someone wanted it to.

There are other sellers of Eurorail passes, including the sponsors of this website. You can research and compare them with the Rail Passes tab at the top of this page.

Choosing a pass really depends on how well planned your itinerary is. To cover longer distances, consider cheap flight hops instead of adding a pass day. For shorter hops, consider bus; a route like Vienna-Bratislava, for example, would be ridiculous to burn a Pass day for; bus makes much more sense on a short route like this.

Railsaver.com is part of this site. Try some itineraries there to see what it recommends. And check out our Transport forum for more help and guidance with trains.

The recommendation from the trip planner is the best general recommendation you’re going to get. Anything better depends on a lot of time and effort on your part checking prices on each individual national rail company website and buying non-refundable advanced purchase specials on those sites.

Your 5 days would be 5 days that you choose within a 2 month period. A rail day is midnight to midnight and you can take as many trains as you like, anywhere in (and between) any of the countries covered by the pass, during that 24 hour period. The special “7 PM rule” means that most overnight trains only count as one day (arrival day) even though you are traveling on both sides of midnight.

Don is right “What’s available right now does not stick around forever.” so it is really depends.