Cheap flights from Orlando Airport to Chicago from $106

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando Airport, with most prices found around $164. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando Airport during the month October is also very affordable. Most momondo users find prices during this month for around $176.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando Airport. The lowest ticket price found for a Friday departure recently was $192. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Orlando Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $332.

Flying to Chicago Midway Airport from Orlando Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $201 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $275. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $265 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Orlando Airport for as low as $159 on momondo.

There are 2 cabin classes available to choose from on Orlando Airport to Chicago Midway Airport 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 8% on your flight if you consider stops on a Orlando Airport to Chicago Midway Airport flight.

As of July 2026, prices for Orlando Airport to Chicago Midway Airport flights are approximately 19% more expensive when compared to flights at the same time last year.

Historically, on average around 23% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 130 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night 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 24% of their flights experiencing any sort of delay.

8 flights are operational daily from Orlando Airport to Chicago Midway Airport as of July 2026. The most popular departure time for this route is 4:00PM, with 45% of flights per day taking off in the afternoon.

62 flights are operational weekly from Orlando Airport to Chicago Midway Airport as of July 2026. The most popular departure day for this route is Sat, with 24% of flights per week taking off on this day.