Cheap flights from Wilmington to Chicago from $127

The month of January is, on average, the cheapest month to fly to Chicago from Wilmington, with most prices found around $306. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Wilmington to Chicago during February average around $323.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $384. 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 Wilmington to Chicago for around $789.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Wilmington to Chicago during this time can be as low as $407. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $527.

Fly from Wilmington New Hanover County to Chicago O'Hare Intl for the best Wilmington New Hanover County - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Wilmington when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $373 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Wilmington for as low as $265 on momondo.

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

American Airlines is the most popular carrier operating from Wilmington New Hanover County to Chicago

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Wilmington according to our data. American Airlines is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

The number of flights available between Wilmington and Chicago is 4 per day as of September 2026. The most frequent departure time is 12:00PM, with 52% of daily flights leaving in the afternoon.

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