Cheap flights from Orlando Airport to Chicago from $104

The month of January is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $176. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Orlando Airport to Chicago during February average around $180.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $300. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $525.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando Airport to Chicago during this time can be as low as $256. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $584.

Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $241 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando Airport for as low as $191 on momondo.

There are 4 cabin classes available to choose from on Orlando Airport to Chicago 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 flight.

As of August 2026, prices for Orlando Airport to Chicago flights are approximately 9% cheaper when compared to flights at the same time last year.

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Orlando to Chicago

Frontier, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Orlando Airport according to our data. Frontier is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 18% 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 150 minutes.

Generally, flights departing in the morning 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

49 flights are operational daily from Orlando Airport to Chicago as of August 2026. The most popular departure time for this route is 4:00PM, with 46% of flights per day taking off in the afternoon.

345 flights are operational weekly from Orlando Airport to Chicago as of August 2026. The most popular departure day for this route is Fri, with 23% of flights per week taking off on this day.