Cheap flights from Orlando to Chicago from R2 833

The month of February is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around R2 816. If you are unable to visit Chicago during the month of February, then departing from Orlando during the month January is also very affordable. Most momondo users find prices during this month for around R3 016.

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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R4 456 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 for as low as R3 899 on momondo.

There is only 1 cabin class available to choose from on Orlando 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 144 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 October 2026, there are 1 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 11:00, with 40% of flights taking off at midday.

The number of flights available between Orlando and Chicago is 9 per week as of October 2026. The most frequent departure day is Fri, with 100% of weekly flights leaving on this day.