Cheap flights from Orlando to Chicago from $104

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando, with most prices found around $37. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Orlando during the month December is also very affordable. Most momondo users find prices during this month for around $48.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando. The lowest ticket price found for a Friday departure recently was $186. 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, Tuesday is the most expensive day to depart from Orlando because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $308.

Flying to Chicago Midway Airport from Orlando at noon is the least expensive time of day to depart. momondo users have found prices as low as $197 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $264. 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $254 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 for as low as $159 on momondo.

There are 2 cabin classes available to choose from on Orlando 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 to Chicago Midway Airport flight.

As of July 2026, prices for Orlando to Chicago Midway Airport flights are approximately 46% 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 129 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 23% of their flights experiencing any sort of delay.

As of July 2026, 7 flights take off from Orlando and land in Chicago Midway Airport each day. The most common flight departure time for this route is 4:00PM, with 45% of daily flights taking off in the afternoon.

As of July 2026, 54 flights take off from Orlando and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.