Cheap flights from Illinois to Puerto Rico

Travel > Caribbean > Puerto Rico

Juan Ponce de León founded the original settlement Caparra in 1508. This settlement was a year later moved to Puerto Rico, as it showed similarity in geographical features to Gran Canaria Island of Canary Islands. In 1521, newer settlement received its name, San Juan Bautista de Puerto Rico, honoring John the Baptist. The name was given based on the tradition for christening the region with both formal name and the one given by Christopher Columbus.... (read more in our San Juan History)

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Chicago 

Check our newest flight offers to Puerto Rico:

  • $222Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)01/14/201807:00 am
    Aguadilla, PR (BQN)Chicago, IL (ORD)01/19/201804:28 am
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  • $228Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/14/201807:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)01/19/201804:28 am
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  • $242Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/14/201807:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)01/19/201802:20 pm
    cheapoair.com check price
  • $331Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/14/201807:29 am
    San Juan, PR (SJU)Chicago, IL (ORD)01/19/201803:07 am
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  • $361Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Ponce, PR (PSE)02/20/201806:49 pm
    Ponce, PR (PSE)Chicago, IL (ORD)03/07/201809:57 am
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San Juan Pictures
  • El Morro - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • El Morro - San Juanview
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