$73 Find Cheap Southwest Flights from Denver to Chicago

When to Book Flights with Southwest from Denver to Chicago

• How far in advance should I book tickets for a flight with Southwest from Denver 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 44 days before departure.

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

  With an average price of $255 return, Southwest is not the cheapest airline to fly from Denver to Chicago with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $167 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Denver to Chicago was $104 for a return flight and $66 for a one-way flight.

• Does Southwest fly direct to Chicago from Denver?

  Yes, Southwest does offer direct flights for the route, with around 40 flights per week.

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

  On average, the cheapest day of the week to fly from Denver to Chicago with Southwest is Tuesday, when prices are around $71. The most expensive day is generally Saturday, where the average price is around $97.

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

  The cheapest month for Southwest flights to Chicago from Denver is generally April, where plane tickets cost $114 on average. If possible, try to avoid the most expensive months of March and October, where tickets cost $181 and $188 respectively.