$80 Find Cheap Southwest Flights from Philadelphia to Chicago

When to Book Flights with Southwest from Philadelphia to Chicago

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

  Generally, when trying to get a below average price for your ticket, try to book around 15 days before departure. For the cheapest possible price, our data suggests booking 78 days before departure.

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

  With an average price of $307 return, Southwest is not the cheapest airline to fly from Philadelphia to Chicago with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $174 on average.

• What is the cheapest Southwest flight from Philadelphia to Chicago?

  In the last 3 days, the lowest price for a flight with Southwest from Philadelphia to Chicago was $92 for a return flight and $44 for a one-way flight.

• Does Southwest fly direct to Chicago from Philadelphia?

  Yes, Southwest does offer direct flights for the route, with around 23 flights per week.

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

  On average, the cheapest day of the week to fly from Philadelphia to Chicago with Southwest is Tuesday, when prices are around $69. The most expensive day is generally Saturday, where the average price is around $105.

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

  The cheapest month for Southwest flights to Chicago from Philadelphia is generally December, where plane tickets cost $109 on average. If possible, try to avoid the most expensive months of July and June, where tickets cost $213 and $290 respectively.