Cheap flights from Chicago to San Juan, Puerto Rico for only $269 roundtrip with JetBlue.DEPART:Chicago, USAARRIVE:San Juan, Puerto RicoRETURN:Chicago, USADATES:Availability from October 2022 to February 2023 (excluding Christmas/New Year)Example dates:25th Oct – 1st NovAdvertisement28th Oct – 4th Nov1st-8th Nov2nd-9th Nov5th-12th Nov21st-28th Jan25th Jan – 1st Feb31st Jan – 7th Feb7th-14th Feband more…STOPS:New YorkAIRLINES:JetBlueGO TO DEAL All the information on this page is accurate at the time of publication.If you are viewing this deal at a later date, the price and availability may no longer be as advertised.To ensure you never miss a Secret Flying deal again, download our FREE smartphone app to receive instant flight deal alerts.AdvertisementCheck prices and Book Cheap flights and hotels NowFind a hotel to go with your flight to San Juan Search Hotels Powered byAdvertisement