Thumb Score: +7 American Airlines offers Round Trip non-stop fares from Chicago (ORD) to San Diego (SAN) for $125. Limited dates travel between September to December 2019. The fare allows 1 personal + 1 carry on. Sample Dates Depart ORD August 31 --- Depart SAN September 5 Depart ORD September 1, 4, 5, 6, 9, 11, 13, 18 --- Depart SAN September 6, 9, 10, 11, 14, 16, 18, 23 Depart ORD October 2, 9, 26 --- Depart SAN October 7, 14, 31 Depart ORD November 9 --- Depart SAN November 14 Depart ORD December 4, 7, 8, 11, 12 --- 9, 12, 13, 16, 17