Fly nonstop from Chicago to San Juan for $265 round-trip, including all taxes, on United.
We found seats departing ORD on Wednesday, April 23, returning from SJU on the following Wednesday, April 30. Other dates are also available for travel through spring, with seats scarce for summer.
Slightly higher fares available for travel this weekend on US Airways, with a connecting flight, for $276 round-trip, departing Friday, April 18, returning April 24.
For a complete look at current deals, visit our San Juan fare page.