Cheap flights from Chicago Midway Airport to Orlando from $59

The month of September is, on average, the cheapest month to fly to Orlando from Chicago Midway Airport, with most prices found around $193. If you’re not able to fly to Orlando in September, then August is your next best option. Flight prices from Chicago Midway Airport to Orlando during August average around $210.

Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $249. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $287.

The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $240. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $291.

Fly from Chicago Midway to Orlando for the best Chicago Midway - Orlando flight prices

You are more likely to see cheaper flights to Orlando from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $277 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Chicago Midway Airport for as low as $206 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway to Orlando flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Orlando flight.

As of April 2026, prices for Chicago Midway Airport to Orlando flights are approximately 121% more expensive when compared to flights at the same time last year.

Southwest, Delta, and Allegiant Air are the most popular carriers operating from Chicago Midway to Orlando

Southwest, Frontier and Delta are the top three most popular airlines that fly to Orlando from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Orlando. Keep in mind that there are 3 different airlines that fly to Orlando on a routine basis, so you have a few additional options to choose from.

Historically, on average around 14% of flights between Chicago and Orlando have experienced a delay on any given week. The average delay length over the past 12 months has been 140 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

As of April 2026, there are 6 flights per day flying from Chicago Midway Airport to Orlando. The most common time of day flights depart is 5:00AM, with 37% of flights taking off in the afternoon.

As of April 2026, there are 45 flights per week flying from Chicago Midway Airport to Orlando. The most common day of the week flights depart is Thu, with 24% of flights taking off on this day.