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Trip to Spain: Madrid, Barcelona & Malaga

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I am planning a trip to see a friend on the southern coast of Spain. It looks like I'll be going during early to late Fall for about 3-weeks. I'm considering flying into Madrid - seems to be the best connection from my departure city, Chicago, then swinging over to Barcelona before heading south, tentatively about 1 week in each location. I first thought of the train for connections between cities in Spain, but discount plane flights appear to be much more reasonable, particularly Barcelona to Malaga.
Despite traveling to Europe several times before, this is my visit to Spain. Suggestions or tips for this trip- including thoughts concerning transportation- would therefore be greatly welcomed.

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