Cheap flights from Greensboro to Chicago from $163

The month of November is, on average, the cheapest month to fly to Chicago from Greensboro, with most prices found around $265. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Greensboro to Chicago during February average around $279.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $364. 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 Greensboro to Chicago for around $666.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Greensboro to Chicago during this time can be as low as $339. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $457.

Fly from Greensboro/H. Point to Chicago O'Hare Intl for the best Greensboro/H. Point - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Greensboro when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Greensboro for as low as $239 on momondo.

There are 4 cabin classes available to choose from on Greensboro to Chicago 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 Greensboro to Chicago.

As of September 2026, prices for Greensboro to Chicago flights are approximately 65% more expensive when compared to flights at the same time last year.

United Airlines and Delta are the most popular carriers operating from Greensboro/H. Point to Chicago

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Greensboro according to our data. American Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of September 2026, 14 flights take off from Greensboro and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 63% of daily flights taking off at noon.

As of September 2026, there are 101 flights per week flying from Greensboro to Chicago. The most common day of the week flights depart is Wed, with 19% of flights taking off on this day.