Fly nonstop from Chicago to San Juan, PR for $276 round-trip on JetBlue.
Searching JetBlue.com, we found seats departing ORD on Tuesday, October 13, returning from SJU on Tuesday, October 20.
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.