Roundtrip Flights Chicago to San Juan Puerto Rico w/ JetBlue

JetBlue and Expedia offer roundtrip airfares between Chicago (ORD) and San Juan, Puerto Rico (SJU) for $150-$160. These basic economy fares include one stop in New York each way and only allow a personal item and a carry-on bag. There is no seat selection or changes, however, JetBlue’s policy ensures families traveling with children will be seated together.

Travel Availability

• Departing ORD: February 24-25; March 2-4, 10-11, 17, 24-25; April 30; May 5-7, 21
• Departing SJU: March 3-5, 10, 18-19, 25; April 13-14; May 19, 25