Roundtrip Airfares: Chicago, IL to/from San Diego, CA via Major Airlines from $157 (Travel January - March 2026)

Roundtrip Airfares: Chicago, IL to/from San Diego, CA via Major Airlines from $156 (Travel January - March 2026). Thumb Score: +12. Alaska, United and American Airlines all have round trip airfares travelling to and from Chicago (ORD) and San Diego (SAN) for $156-$177, nonstop. There are very limited dates for the $156 airfare but more choices for the $177. These are basic economy fares. 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. Travel Availability: Departs ORD: Jan 6-7, 10, 13-14, 17, 20-21, 24, 27-28, 31; Feb 3-4, 7, 10-11, 14, 17-21, 24-25, 28; March 3-4