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Es correcto decir 'Voy a Chicago' y 'Voy para Chicago' (I'm going to Chicago)?

If so , how and when 'a' and 'para' are different?

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Usado con verbos de movimiento como «ir» y con lugares hay una diferencia:

Voy a Chicago.

Tienes asuntos que hacer en Chicago. Chicago es el destino de un viaje que planeas hacer o estás haciendo.

Voy para Chicago.

Estás en camino, en movimiento o a punto de partir. El destino (final o inmediato) del itinerario es Chicago, pero Chicago es más un referente que un propósito.

Estos sentidos son algo intercambiables y la preposición afecta más el sentido del verbo, en este caso «ir» entre un viajar como un propósito («ir a Chicago») o como un proceso («ir para Chicago»).

Using with movement verbs such as «ir» and with places there is a difference:

Voy a Chicago

You have business in Chicago. Chicago is the destination of a trip you are planning to do or you are doing.

Voy para Chicago

You are in motion or next to depart. The (final or intermediate) destination is Chicago, but Chicago is rather a geographical reference than a purpose.

These senses might be a little exchangeable and the preposition rathers affect the verb, in this case «ir» from traveling as a purpose («ir a Chicago») and as a process («ir para Chicago»).

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Había un chiste de un gallego que no sabía decir si iba a Lugo o para Lugo... – Bardo Dec 17 '13 at 11:38

'a' is mostly used for a destiny:

"Voy a Chicago" (destiny)

"Voy a la entrega de premios" (the destiny of the trip is the award dining itself)

'para' is mostly used for a reason:

"Voy a Chicago para la entrega de premios" (the destiny of the trip is Chicago, as a whole, you may spend some days there, but the reason you are going to Chicago is the award dining)

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a y para son preposiciones que pueden ser utilizadas de forma indistinta, cuando te refieres a un punto al que te dirijas como en tus ejemplos

  • Voy a Chicago
  • Voy para Chicago

a and para are prepositions that can be used without changing the meaning of your phrase, when you're talking about somewhere you are giong to, like in your samples

  • Voy a Chicago
  • Voy para Chicago
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As a rule of thumb, you could use "a" if you can substitute with "towards" in the english version; and you could use "para" if you can substitute with "to" or "for". This is very rough, but could help you in case of doubt.

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