For peak holiday travel, fly nonstop from Chicago to San Diego for $383 roundtrip on American Airlines.
Searching AA.com, we found seats departing ORD on Tuesday, December 24, Christmas Eve, returning from SAN on Wednesday, January 1, New Year's Day. Best of all, this is a main cabin fare, meaning it isn't in basic economy like so many holiday deals.
As always, you'll find lower fares available for non-holiday travel.
For a look at more great deals, see our complete listings for Chicago ORD.