Chicago to San Diego $82 Round-Trip, Nonstop, on Southwest

Fly nonstop from Chicago to San Diego for $82 round-trip on Southwest.

Searching Southwest, we found seats departing MDW on Tuesday, September 27, returning from SAN on Saturday, October 1.

Other dates are also available for travel from August through November.

See our fare details for booking info.

Need a room in San Diego? Here's what's available for the above dates on Hotelwatchdog.