Fly nonstop from Chicago to San Juan, PR for $276 round-trip on United.
Searching United.com, we found seats departing ORD on Monday, November 2, returning from SJU on Tuesday, November 10.
Other dates are also available for travel in fall.
See our fare details for booking info.
Need a room in San Juan? Here's what's available for the above dates on Hotelwatchdog.