Cheap Flights from San Juan to Chicago* All One Way Round Trip CHISan Juan → ChicagoOne Way Trip | Jun 3$101.81 Book Now CHISan Juan → ChicagoOne Way Trip | Jun 7$169.75 Book Now CHISan Juan ⇌ ChicagoRound Trip | Jun 3 - Jun 24$210.99Book Now CHISan Juan ⇌ ChicagoRound Trip | Aug 15 - Aug 22$326.82Book Now * All fares above were last found on: May 12, 2025 at 8:24 PM. Fares are one way or round trip as indicated aboveround trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions. 202505~Ref:3k6lIwAOGUyVRDWZ-z1y1Q
Our Lowest Fare* All fares below were last found on: . Fares are round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions.
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Search Cheap Flights from San Juan to ChicagoBook your flights from San Juan to Chicago and on airfares. Have passion for excellent music, spectacular architecture and amazing art, then Chicago is definitely the destination for you. Most populous city in Illinois, US, a vacation in Chicago would certainly refresh your soul. Plan a picnic at Millennium Park which is decorated with beautiful art and architecture and is also popular for its ice rink and theatre performances. Watch some of the best dramas at the Chicago Shakespeare Theater and don’t forget to enjoy 360 degree views of the city from the top of Willis Tower which also boasts of spectacular architecture.To reach Chicago from San Juan, you may choose amongst the premier airlines such as US Airways, American Airlines, Air Tran Airways and United Airlines. Your flight to Chicago from San Juan takes about five hours and fifty minutes to cover a distance of about 2,061 miles excluding layover time, so make sure you have a good book or an interesting company to keep yourself engaged for the travel.
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