* All fares below were last found on: Nov 20, 2018 and 7:22:27 AM.
Fares are round trip, Fares incl. all fuel surcharges, our service fees and taxes.
Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking.
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Book your flights from Chicago to San Juan and save big on airfares. Check out the Spanish heritage or take a stroll in its colonial neighborhoods, San Juan is one of the pleasant destinations to visit and explore. It is the capital and the most populous municipality in Puerto Rico.
To reach San Juan from Chicago, you can choose amongst the top airline that includes US Airways and American Airlines. Take advantage of exclusive deals on flights to San Juan and save more to splurge on a vacation. Your flight to San Juan from Chicago takes about seven hours thirty minutes to cover a distance of about 2051 miles excluding layover time. For passing time watching in-flight movie is the best bet.