$79 Find Cheap Southwest Flights from Chicago to Miami

When to Book Flights with Southwest from Chicago to Miami

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

  Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 67 days before departure.

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

  With an average price of $368 return, Southwest is not the cheapest airline to fly from Chicago to Miami with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $189 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to Miami was $100 for a return flight and $48 for a one-way flight.

• Does Southwest fly direct to Miami from Chicago?

  Yes, Southwest does offer direct flights for the route, with around 4 flights per week.

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

  On average, the cheapest day of the week to fly from Chicago to Miami with Southwest is Saturday, when prices are around $68. The most expensive day is generally Thursday, where the average price is around $97.

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

  The cheapest month for Southwest flights to Miami from Chicago is generally September, where plane tickets cost $78 on average. If possible, try to avoid the most expensive months of March and December, where tickets cost $245 and $309 respectively.