Cheap flights from Orlando to Chicago from $105

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Orlando averaging around $186.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $327. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Orlando because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $621.

Flying to Chicago O'Hare Intl Airport from Orlando in the evening is the least expensive time of day to depart. momondo users have found prices as low as $267 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $814. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $241 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Orlando for as low as $191 on momondo.

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

United Airlines, JetBlue, and Delta are the most popular carriers operating from Orlando to Chicago O'Hare Intl

Frontier, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Orlando according to our data. Frontier is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 15% 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 164 minutes.

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

Wednesday 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 9% of their flights experiencing any sort of delay.

As of August 2026, 54 flights take off from Orlando and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 4:00PM, with 47% of daily flights taking off in the afternoon.

As of August 2026, 378 flights take off from Orlando and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.