Cheap flights from Orlando Airport to Chicago from £85

The cheapest month to fly to Chicago from Orlando Airport is in January. Flight prices, which tend to average around £130, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago from Orlando Airport during February instead. Flights to Chicago in February, while not as cheap as those in January, still average around £133.

Fly from Orlando to Chicago Midway 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 £182 when searching weeks before you fly. 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 £147 on momondo.

There are 3 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.

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 149 minutes.

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

Wednesday is statistically the day of the week that experiences the fewest 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 fewest delays on this route over the last 12 months, with about 9% of their flights experiencing any sort of delay.

As of August 2026, there are 42 flights per day flying from Orlando Airport to Chicago. The most common time of day flights depart is 11:00, with 50% of flights taking off at midday.

The number of flights available between Orlando Airport and Chicago is 297 per week as of August 2026. The most frequent departure day is Sat, with 23% of weekly flights leaving on this day.