Find cheap Southwest flights to Chicago

When to Book Flights with Southwest from Dallas/Fort Worth Airport to Chicago

• How far in advance should I book tickets for a flight with Southwest from Dallas/Fort Worth Airport to Chicago?

  Generally, when trying to get a below average price for your ticket, try to book around 14 days before departure. For the cheapest possible price, our data suggests booking 44 days before departure.

• Is Southwest the cheapest airline to fly with from Dallas/Fort Worth Airport to Chicago?

  With an average price of $274 return, Southwest is not the cheapest airline to fly from Dallas/Fort Worth Airport to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $137 on average.

• What is the cheapest Southwest flight from Dallas/Fort Worth Airport to Chicago?

  In the last 3 days, the lowest price for a flight with Southwest from Dallas/Fort Worth Airport to Chicago was $79 for a return flight and $42 for a one-way flight.

• Does Southwest fly direct to Chicago from Dallas/Fort Worth Airport?

  No, Southwest does not fly the route directly.

• What’s the cheapest day of the week to fly from Dallas/Fort Worth Airport to Chicago with Southwest?

  On average, the cheapest day of the week to fly from Dallas/Fort Worth Airport to Chicago with Southwest is Monday, when prices are around $46. The most expensive day is generally Thursday, where the average price is around $90.

• What’s the cheapest month to fly from Dallas/Fort Worth Airport to Chicago with Southwest?

  The cheapest month for Southwest flights to Chicago from Dallas/Fort Worth Airport is generally October, where plane tickets cost $98 on average. If possible, try to avoid the most expensive months of March and November, where tickets cost $232 and $250 respectively.