$69 Find Cheap Southwest Flights from Chicago to Orlando

When to Book Flights with Southwest from Chicago to Orlando

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

  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 42 days before departure.

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

  With an average price of $358 return, Southwest is not the cheapest airline to fly from Chicago to Orlando with. Instead, for the lowest price, our data suggests flying with Allegiant Air, where a return flight costs $178 on average.

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

  In the last 3 days, the lowest price for a flight with Southwest from Chicago to Orlando was $89 for a return flight and $40 for a one-way flight.

• Does Southwest fly direct to Orlando from Chicago?

  Yes, Southwest does offer direct flights for the route, with around 71 flights per week.

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

  On average, the cheapest day of the week to fly from Chicago to Orlando with Southwest is Monday, when prices are around $72. The most expensive day is generally Wednesday, where the average price is around $101.

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

  The cheapest month for Southwest flights to Orlando from Chicago is generally September, where plane tickets cost $98 on average. If possible, try to avoid the most expensive months of March and January, where tickets cost $241 and $293 respectively.