$70 Find Cheap Southwest Flights from Chicago to Philadelphia

When to Book Flights with Southwest from Chicago to Philadelphia

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

  Generally, when trying to get a below average price for your ticket, try to book around 13 days before departure. For the cheapest possible price, our data suggests booking 71 days before departure.

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

  With an average price of $303 return, Southwest is not the cheapest airline to fly from Chicago to Philadelphia with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $166 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to Philadelphia was $88 for a return flight and $53 for a one-way flight.

• Does Southwest fly direct to Philadelphia from Chicago?

  Yes, Southwest does offer direct flights for the route, with around 5 flights per week.

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

  On average, the cheapest day of the week to fly from Chicago to Philadelphia with Southwest is Monday, when prices are around $61. The most expensive day is generally Wednesday, where the average price is around $98.

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

  The cheapest month for Southwest flights to Philadelphia from Chicago is generally February, where plane tickets cost $109 on average. If possible, try to avoid the most expensive months of November and March, where tickets cost $262 and $315 respectively.