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Sky High Flight Facts for Your Trip: Chicago to San Juan

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.

  • When does the earliest flight depart Chicago? 7:25AM  JetBlue Airways  Flight #1563
  • When does the latest flight depart San Juan? 10:49PM  United Airlines   Flight #982
  • What is the busiest month to travel from Chicago to San Juan?December
  • What is the least busy month to travel from Chicago to San Juan?June