$82 Find Cheap Southwest Flights from San Diego to Chicago

When to Book Flights with Southwest from San Diego to Chicago

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

  With an average price of $415 return, Southwest is not the cheapest airline to fly from San Diego to Chicago with. Instead, for the lowest price, our data suggests flying with Hawaiian Airlines, where a return flight costs $197 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from San Diego to Chicago was $158 for a return flight and $77 for a one-way flight.

• Does Southwest fly direct to Chicago from San Diego?

  Yes, Southwest does offer direct flights for the route, with around 17 flights per week.

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

  On average, the cheapest day of the week to fly from San Diego to Chicago with Southwest is Tuesday, when prices are around $85. The most expensive day is generally Saturday, where the average price is around $155.

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

  The cheapest month for Southwest flights to Chicago from San Diego is generally February, where plane tickets cost $180 on average. If possible, try to avoid the most expensive months of March and December, where tickets cost $281 and $459 respectively.