Cheap flights from Chicago to Orlando from ₹ 10,474

The month of January is, on average, the cheapest month to fly to Orlando from Chicago, with most prices found around ₹ 20,282. If you aren’t able to travel to Orlando during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of ₹ 22,091.

The cheapest day to depart from Chicago to Orlando is on a Saturday when prices can be found for as low as ₹ 26,965. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Orlando for around ₹ 38,553.

Our data shows that the cheapest Chicago to Orlando flights are usually those with departure times in the afternoon. Our users have found flights to Orlando in the afternoon for as low as ₹ 26,965. Try not to purchase tickets in the evening because they tend to be around ₹ 38,553. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 ₹ 30,716 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Chicago for as low as ₹ 25,804 on momondo.

There is only 1 cabin class 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.

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 147 minutes.

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

Wednesday 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 15% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Orlando is 52 per day as of October 2026. The most frequent departure time is 11:00, with 44% of daily flights leaving at midday.

364 flights are operational weekly from Chicago to Orlando as of October 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.