Cheap flights from Chicago Midway Airport to Orlando from $102

The cheapest month to fly to Orlando Airport from Chicago Midway Airport is in February. Flight prices, which tend to average around $193, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Orlando Airport from Chicago Midway Airport during January instead. Flights to Orlando Airport in January, while not as cheap as those in February, still average around $208.

The cheapest day to depart from Chicago Midway Airport to Orlando Airport is on a Tuesday. Travelers who choose to depart for Orlando Airport on a Tuesday will often find tickets for as low as $303. The most expensive day to fly to Orlando Airport is Monday, with ticket prices averaging around $364.

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Orlando Airport when you can find flight prices for as low as $286. Flying to Orlando Airport in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $357.

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

You are more likely to see cheaper flights to Orlando Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando Airport for around $354 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando Airport from Chicago Midway Airport for as low as $277 on momondo.

There are 2 cabin classes available to choose from on Chicago Midway Airport to Orlando Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Orlando Airport.

As of October 2026, prices for Chicago Midway Airport to Orlando Airport flights are approximately 31% more expensive when compared to flights at the same time last year.

Historically, on average around 17% 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 135 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.

Wednesday 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 17% of their flights experiencing any sort of delay.

The number of flights available between Chicago Midway Airport and Orlando Airport is 6 per day as of October 2026. The most frequent departure time is 8:00AM, with 52% of daily flights leaving at noon.

As of October 2026, there are 44 flights per week flying from Chicago Midway Airport to Orlando Airport. The most common day of the week flights depart is Mon, with 34% of flights taking off on this day.