Cheap flights from Orlando to Chicago from £53

The cheapest month to fly to Chicago from Orlando is in September. Flight prices, which tend to average around £87, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Orlando during February instead. Flights to Chicago in February, while not as cheap as those in September, still average around £98.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £227. 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 Friday, with ticket prices averaging around £415.

Flying to Chicago from Orlando in the morning is the least expensive time of day to depart. momondo users have found prices as low as £246 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £263.

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 £124 on momondo.

There are 3 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.

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 60 per day as of March 2026. The most frequent departure time is 14:00, with 43% of daily flights leaving in the afternoon.

As of March 2026, 423 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.