$49 Find Cheap Southwest Flights from Pittsburgh to Chicago

When to Book Flights with Southwest from Pittsburgh to Chicago

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

  With an average price of $317 return, Southwest is not the cheapest airline to fly from Pittsburgh to Chicago with. Instead, for the lowest price, our data suggests flying with American Airlines, where a return flight costs $297 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Pittsburgh to Chicago was $97 for a return flight and $68 for a one-way flight.

• Does Southwest fly direct to Chicago from Pittsburgh?

  Yes, Southwest does offer direct flights for the route, with around 21 flights per week.

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

  On average, the cheapest day of the week to fly from Pittsburgh to Chicago with Southwest is Monday, when prices are around $38. The most expensive day is generally Thursday, where the average price is around $114.

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

  The cheapest month for Southwest flights to Chicago from Pittsburgh is generally September, where plane tickets cost $45 on average. If possible, try to avoid the most expensive months of December and January, where tickets cost $272 and $331 respectively.