Cheap flights from Greenville to Chicago from $114

The month of November is, on average, the cheapest month to fly to Chicago from Greenville, with most prices found around $81. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from Greenville to Chicago during September average around $90.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $378. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Greenville to Chicago for around $672.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Greenville to Chicago during this time can be as low as $318. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $929.

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

You are more likely to see cheaper flights to Chicago from Greenville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $294 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Greenville for as low as $202 on momondo.

You could potentially save up to 24% on your flight if you consider stops on a Greenville to Chicago flight.

As of May 2026, prices for Greenville to Chicago flights are approximately 30% cheaper when compared to flights at the same time last year.

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

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Greenville according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

23 flights are operational daily from Greenville to Chicago as of May 2026. The most popular departure time for this route is 5:00PM, with 54% of flights per day taking off at noon.

As of May 2026, 163 flights take off from Greenville and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.