Roundtrip Nonstop Flights: Chicago, IL (ORD) to/from San Diego, CA (SAN) $139 (Travel late-Aug to mid-Dec, 2025)

Roundtrip Nonstop Flights: Chicago, IL (ORD) to/from San Diego, CA (SAN) $139 (Travel late-Aug to mid-Dec, 2025). Thumb Score: +13. Alaska, United, American and Expedia have round trip airfares traveling to and from Chicago (ORD) and San Diego (SAN) for $139 nonstop. On Alaska and American, you may have a personal item and a carry-on bag. On United, you may only have a personal item. There is no seat selection and no change. If you are traveling with children, you will be seated together as per their policies. Travel Availability: Departs ORD: Aug 26-27, 30; Sept 6, 9-10, 13, 16-17, 20, 23-24, 27, 30; Oct 1, 4, 7-8, 11, 14-15, 18, 21-22, 25, 28-29; Nov 1, 4-5, 8, 11-12, 15, 18-19; Dec 3, 6, 9-10, 13, 16-17