Cheap flights from Chicago to Orlando from $105

The cheapest month to fly to Orlando Airport from Chicago is in January. Flight prices, which tend to average around $216, 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 Orlando Airport from Chicago during September instead. Flights to Orlando Airport in September, while not as cheap as those in January, still average around $238.

The cheapest day to depart from Chicago to Orlando Airport is on a Tuesday. Travelers who choose to depart for Orlando Airport on a Tuesday will often find tickets for as low as $291. The most expensive day to fly to Orlando Airport is Sunday, with ticket prices averaging around $340.

In the evening is the cheapest time of day to fly from Chicago to Orlando Airport when you can find flight prices for as low as $266. Flying to Orlando Airport in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $331.

Fly from Chicago O'Hare Intl to Orlando for the best Chicago - Orlando flight prices

You are more likely to see cheaper flights to Orlando Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando Airport for around $291 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando Airport from Chicago for as low as $243 on momondo.

There are 4 cabin classes available to choose from on Chicago to Orlando Airport 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 17% on your flight if you consider stops on a Chicago to Orlando Airport flight.

As of August 2026, prices for Chicago to Orlando Airport flights are approximately 23% cheaper when compared to flights at the same time last year.

Southwest, Delta, and United Airlines are the most popular carriers operating from Chicago to Orlando

United Airlines, Frontier and American Airlines are the top three most popular airlines that fly to Orlando Airport from Chicago according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Orlando Airport. Keep in mind that there are 6 different airlines that fly to Orlando Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Chicago and Orlando have experienced a delay on any given week. The average delay length over the past 12 months has been 148 minutes.

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

Tuesday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 15% of their flights experiencing any sort of delay.

As of August 2026, there are 47 flights per day flying from Chicago to Orlando Airport. The most common time of day flights depart is 5:00PM, with 50% of flights taking off at noon.

As of August 2026, there are 334 flights per week flying from Chicago to Orlando Airport. The most common day of the week flights depart is Mon, with 25% of flights taking off on this day.