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Boston Airport - A to E

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We are flying Denver to Boston to Spain, on Southwest we would arrive 3:35 pm at Con. A and have to go to Con. E where Iberia departs at 5:40pm. I'm afraid of not having enough time to get suitcases from carrousel and checked them in Iberia on time. I assume we have to go into security again?

Will SW 3:35pm arriving to 5:40 pm departing have enough time in between to get from A to E?
Our other option would be flying UA to Boston arriving 2:05pm to Iberia E 5:40 pm.

Flights are getting more expensive as times go by and Soutwhest is cheaper at this point with free luggage.

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