Cheap flights from Chicago to Orlando from $58

The month of August is, on average, the cheapest month to fly to Orlando from Chicago, with most prices found around $170. If you’re not able to fly to Orlando in August, then September is your next best option. Flight prices from Chicago to Orlando during September average around $193.

Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $248. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $286.

The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $238. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $287.

Fly from Chicago Greater Rockford to Orlando Sanford Intl for the best Chicago - Orlando flight prices

You are more likely to see cheaper flights to Orlando from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando 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 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.

As of March 2026, prices for Chicago to Orlando flights are approximately 42% more expensive when compared to flights at the same time last year.

Allegiant Air, 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 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. Keep in mind that there are 8 different airlines that fly to Orlando 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 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, 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 45 flights per day flying from Chicago to Orlando. The most common time of day flights depart is 9:00AM, with 43% of flights taking off at noon.

As of March 2026, 315 flights take off from Chicago and land in Orlando each week. The most common flight departure day for this route is Thu, with 25% of weekly flights taking off on this day.