Fly nonstop from Chicago to San Diego for $158 round-trip on Southwest.
Seen below, we found seats departing MDW on Wednesday, August 19, returning from SAN on Tuesday, August 25.
Other dates are also available for travel throughout August.
For booking info, see our Fare Details.
Need a room in San Diego? Here's a look at what's available for the above dates on Hotelwatchdog.
All products and services mentioned on Airfarewatchdog are independently selected by our team of expert travelers. If you buy something through our links, we may earn an affiliate commission.
