Fly nonstop from Chicago to San Juan, PR for $286 round-trip on American Airlines.
Searching AA.com, we found seats departing ORD on Wednesday, October 28, returning from SJU on Monday, November 2.
Other dates are also available for travel through early May, 2016.
See our fare details for booking info.
Need a room in San Juan? Here's what's available for the above dates on Hotelwatchdog.
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