Cheap flights from Orlando to Chicago from £62

The cheapest month to fly to Chicago from Orlando is in October. Flight prices, which tend to average around £138, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of October, then book flights to Chicago from Orlando during August instead. Flights to Chicago in August, while not as cheap as those in October, still average around £146.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £222. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Saturday, with ticket prices averaging around £238.

Flying to Chicago from Orlando at midday is the least expensive time of day to depart. momondo users have found prices as low as £222 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £241.

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 £160 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 £118 on momondo.

Historically, on average around 17% 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 155 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.

Tuesday 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.

The number of flights available between Orlando and Chicago is 51 per day as of May 2026. The most frequent departure time is 14:00, with 44% of daily flights leaving in the afternoon.

As of May 2026, 357 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.