$79 Find Cheap Southwest Flights from Chicago to San Diego

When to Book Flights with Southwest from Chicago to San Diego

• Is Southwest the cheapest airline to fly with from Chicago to San Diego?

  With an average price of $460 return, Southwest is not the cheapest airline to fly from Chicago to San Diego with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $203 on average.

• What is the cheapest Southwest flight from Chicago to San Diego?

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to San Diego was $144 for a return flight and $76 for a one-way flight.

• Does Southwest fly direct to San Diego from Chicago?

  Yes, Southwest does offer direct flights for the route, with around 30 flights per week.

• What’s the cheapest day of the week to fly from Chicago to San Diego with Southwest?

  On average, the cheapest day of the week to fly from Chicago to San Diego with Southwest is Sunday, when prices are around $78. The most expensive day is generally Saturday, where the average price is around $117.

• What’s the cheapest month to fly from Chicago to San Diego with Southwest?

  The cheapest month for Southwest flights to San Diego from Chicago is generally September, where plane tickets cost $114 on average. If possible, try to avoid the most expensive months of January and December, where tickets cost $271 and $365 respectively.