$99 Find Cheap Southwest Flights from Los Angeles to Chicago

When to Book Flights with Southwest from Los Angeles to Chicago

• How far in advance should I book tickets for a flight with Southwest from Los Angeles to Chicago?

  Generally, when trying to get a below average price for your ticket, try to book around 16 days before departure. For the cheapest possible price, our data suggests booking 79 days before departure.

• Is Southwest the cheapest airline to fly with from Los Angeles to Chicago?

  With an average price of $364 return, Southwest is not the cheapest airline to fly from Los Angeles to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $215 on average.

• What is the cheapest Southwest flight from Los Angeles to Chicago?

  In the last 3 days, the lowest price for a flight with Southwest from Los Angeles to Chicago was $164 for a return flight and $86 for a one-way flight.

• Does Southwest fly direct to Chicago from Los Angeles?

  Yes, Southwest does offer direct flights for the route, with around 19 flights per week.

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

  On average, the cheapest day of the week to fly from Los Angeles to Chicago with Southwest is Friday, when prices are around $82. The most expensive day is generally Sunday, where the average price is around $118.

• What’s the cheapest month to fly from Los Angeles to Chicago with Southwest?

  The cheapest month for Southwest flights to Chicago from Los Angeles is generally October, where plane tickets cost $159 on average. If possible, try to avoid the most expensive months of March and September, where tickets cost $281 and $349 respectively.