Plan a getaway from the Midwest’s winter! Nonstop flights to San Juan, Puerto Rico, from Chicago are now available for just $287 roundtrip, including taxes. Fare Calendar:


  • This fare represents a savings of up to $150 off typical rountrip pricing.

Travel Dates:

  • Departures available on select dates from November – April. The weeks surrounding and including Thanksgiving, Christmas and New Year’s are blacked out at this price.

Sample Screenshots:


Chicago-San Juan: Search Results

Chicago-San Juan: jetBlue Results Page Updates

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Featured Image: Luquillo Beach (

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Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

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