Cheap flights from Chicago to Orlando from $58

The cheapest month to fly to Orlando Airport from Chicago is in September. Flight prices, which tend to average around $199, 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 Orlando Airport from Chicago during January instead. Flights to Orlando Airport in January, while not as cheap as those in September, still average around $216.

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 $248. The most expensive day to fly to Orlando Airport is Monday, with ticket prices averaging around $294.

In the afternoon is the cheapest time of day to fly from Chicago to Orlando Airport when you can find flight prices for as low as $241. Flying to Orlando Airport in the afternoon is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $289.

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 $262 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 $224 on momondo.

There are 4 cabin classes available to choose from on Chicago to Orlando flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago to Orlando Airport.

As of March 2026, prices for Chicago to Orlando Airport flights are approximately 32% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Spirit 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 29% of people opting to fly with this airline when traveling to Orlando Airport. Keep in mind that there are 7 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 17% 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 149 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, Southwest have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

As of March 2026, there are 48 flights per day flying from Chicago to Orlando Airport. The most common time of day flights depart is 9:00AM, with 43% of flights taking off at noon.

As of March 2026, there are 339 flights per week flying from Chicago to Orlando Airport. The most common day of the week flights depart is Fri, with 24% of flights taking off on this day.