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Travel from US (ORD) to Canary Islands

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Hello, in May 2016 we are travelling from Chicago (O'Hare) through Madrid and on to Las Palmas Gran Canaria. I would like to know more about Immigration and Customs. On the way, do we "clear" immigration in Madrid and our checked bags go through to the island or do we collect our bags in Madrid and re-check? More importantly for the return we leave the island around 6:30pm and arrive Madrid around 10:30pm where I have booked an airport hotel. Will we be reunited with our checked baggage in Madrid that evening or will the bags be checked through to Chicago, requiring us to carry on overnight stay bags? (Sorry, I have travelled internationally before but there was never an overnight stay involved)

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