$69 Find Cheap Southwest Flights from Chicago to Orlando Airport

When to Book Flights with Southwest from Chicago to Orlando Airport

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

  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 45 days before departure.

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

  With an average price of $358 return, Southwest is not the cheapest airline to fly from Chicago to Orlando Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $184 on average.

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

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

• Does Southwest fly direct to Orlando Airport 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 Airport with Southwest?

  On average, the cheapest day of the week to fly from Chicago to Orlando Airport with Southwest is Monday, when prices are around $78. The most expensive day is generally Thursday, where the average price is around $109.

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

  The cheapest month for Southwest flights to Orlando Airport from Chicago is generally February, where plane tickets cost $112 on average. If possible, try to avoid the most expensive months of December and March, where tickets cost $242 and $246 respectively.