Cheap flights from Orlando to Chicago from €98

The cheapest month to fly to Chicago from Orlando is in February. Flight prices, which tend to average around €150, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago in February, then you should wait until January to fly from Orlando, when ticket prices are also cheap, with an average price of €156.

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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around €234 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 €203 on momondo.

There are 2 cabin classes 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.

You could potentially save up to 19% on your flight if you consider stops on a Orlando to Chicago flight.

As of October 2026, prices for Orlando to Chicago flights are approximately 33% cheaper when compared to flights at the same time last year.

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, 62 flights take off from Orlando and land in Chicago each day. The most common flight departure time for this route is 14:00, with 45% of daily flights taking off in the afternoon.

437 flights are operational weekly from Orlando to Chicago as of October 2026. The most popular departure day for this route is Fri, with 16% of flights per week taking off on this day.