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$85+ Cheap flights from Wilmington (ILM) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ILM — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Wilmington New Hanover County to Chicago are usually found in January or February, booked 87 days in advance, depart on a Saturday or Wednesday and return on a Tuesday

Cheap flight deals from Wilmington to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Wilmington (ILM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$165
(Kiwi.com)

One-way from

$98
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$333

Good round-trip deal

$324 or less

Good one-way deal

$248 or less
Provider with most accurate pricing for Wilmington New Hanover County-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Wilmington New Hanover County-Chicago (CHI) flights.
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From Wilmington New Hanover County to Chicago (CHI)
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One-way flight from Wilmington New Hanover County to Chicago (CHI)
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Highest demand for flights based on searches. 15% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Wilmington New Hanover County to Chicago (CHI).
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Price to beat on a one-way flight from Wilmington New Hanover County to Chicago (CHI).
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Find flight deals from Wilmington to Chicago

Cheapest flights from Wilmington to Chicago
Explore the most affordable flight options available from Wilmington to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:10 pmILM - ORD
1 stop21h 55mMultiple Airlines
Thu 1/87:00 amORD - ILM
1 stop13h 29mMultiple Airlines
Deal found 10/29$165
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:17 pmILM - ORD
1 stop20h 51mMultiple Airlines
Thu 1/87:00 amORD - ILM
1 stop13h 29mMultiple Airlines
Deal found 10/29$169
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:46 pmILM - ORD
2 stops25h 08mMultiple Airlines
Thu 1/87:00 amORD - ILM
1 stop13h 29mMultiple Airlines
Deal found 10/29$189
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:10 pmILM - ORD
1 stop21h 55mMultiple Airlines
Mon 2/97:00 amORD - ILM
1 stop13h 27mMultiple Airlines
Deal found 10/29$193
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:17 pmILM - ORD
1 stop20h 51mMultiple Airlines
Mon 1/127:00 amORD - ILM
1 stop13h 27mMultiple Airlines
Deal found 10/29$197
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:17 pmILM - ORD
1 stop20h 51mMultiple Airlines
Sun 2/87:00 amORD - ILM
1 stop13h 29mMultiple Airlines
Deal found 10/29$201
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:10 pmILM - ORD
1 stop21h 55mMultiple Airlines
Sat 1/103:24 pmORD - ILM
2 stops16h 21mMultiple Airlines
Deal found 10/29$207
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:10 pmILM - ORD
1 stop21h 55mMultiple Airlines
Tue 2/104:45 pmORD - ILM
2 stops39h 00mMultiple Airlines
Deal found 10/29$208
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:10 pmILM - ORD
1 stop21h 55mMultiple Airlines
Wed 2/112:47 pmORD - ILM
2 stops29h 42mMultiple Airlines
Deal found 10/29$209
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:17 pmILM - ORD
1 stop9h 52mMultiple Airlines
Mon 12/87:10 amORD - ILM
1 stop11h 37mMultiple Airlines
Deal found 10/29$210
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:17 pmILM - MDW
2 stops18h 29mMultiple Airlines
Sun 1/1110:18 amMDW - ILM
1 stop10h 11mMultiple Airlines
Deal found 10/29$223
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/81:00 pmILM - MDW
1 stop9h 58mMultiple Airlines
Wed 1/76:00 amMDW - ILM
2 stops25h 45mMultiple Airlines
Deal found 10/29$242

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wilmington to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Wilmington to Chicago that are best for you.

Fly from

Wilmington

Fly to

Chicago

Route

Depart

Return

Price

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Wed 12/10

10:26 am-4:34 pm

1 stop7h 08m

Chicago Midway

Thu 1/8

6:45 am-1:45 pm

1 stop6h 00m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Thu 12/4

6:02 pm-11:47 pm

1 stop6h 45m

Chicago Midway

Mon 12/8

6:00 am-1:37 pm

1 stop6h 37m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Tue 12/9

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Tue 2/10

6:17 pm-11:53 pm

1 stop4h 36m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Sun 12/7

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Wed 1/14

6:45 am-1:45 pm

1 stop6h 00m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Mon 12/8

10:26 am-4:34 pm

1 stop7h 08m

Chicago Midway

Tue 2/10

6:00 am-1:31 pm

1 stop6h 31m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Sun 12/14

6:02 pm-11:47 pm

1 stop6h 45m

Chicago Midway

Thu 1/8

6:45 am-1:45 pm

1 stop6h 00m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Sat 3/21

4:30 pm-9:46 pm

1 stop6h 16m

Chicago Midway

Tue 3/24

5:25 pm-11:54 pm

1 stop5h 29m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Wed 12/10

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Wed 1/14

6:45 am-1:45 pm

1 stop6h 00m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Sun 12/7

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Mon 2/9

6:17 pm-11:53 pm

1 stop4h 36m

$249

WilmingtonChicago

ILM - MDW

ILMMDW

Wilmington New Hanover County

Thu 12/11

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Mon 2/9

6:17 pm-11:53 pm

1 stop4h 36m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 37 results
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Compare providers for flights from Wilmington to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Wilmington to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Wilmington-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Wilmington-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Wilmington-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Wilmington-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Wilmington-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Wilmington to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Wilmington with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wilmington to Chicago

How far ahead should I book a flight from Wilmington to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Wilmington to Chicago. Price data was last updated on October 24, 2025.

The price you pay for your flight from Wilmington to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 28 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Wilmington to Chicago?

Currently, June is the cheapest month in which you can book a flight from Wilmington to Chicago (average of $98). Flying from Wilmington to Chicago in February is currently the most expensive (average of $228). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ILM to CHI?

Find hourly flight availability from Wilmington to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Wilmington to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Wilmington to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Wilmington to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wilmington to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Wilmington to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,035 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Wilmington to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Wilmington to Chicago?

    Wilmington New Hanover County (ILM), located 4.3 mi from the city center, is the airport you fly out of when you book flights from Wilmington to Chicago. 2 airlines have flights from New Hanover County to Chicago on a regular basis. Booking flights from Wilmington New Hanover County to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • How long is the flight from Wilmington to Chicago?

    For as low as $249, Delta can have you in Chicago from Wilmington in 7h 08m. There are 745 mi between Wilmington and Chicago.

  • What are the cheapest airlines flying from Wilmington to Chicago round-trip?

    According to our current data, American Airlines ($209), and United Airlines ($249) offers the cheapest pricing from Wilmington to Chicago. American Airlines is 36% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Wilmington to Chicago?

    The top 3 most reliable airlines when flying from Wilmington to Chicago are Qatar Airways (92%), American Airlines (89%) and Envoy Air (89%).

  • What are the cheapest flights from Wilmington to Chicago?

    On average you can expect to pay $339 for a flight from Wilmington to Chicago. The cheapest flight overall is $168 while the most popular route, (Wilmington New Hanover County - Chicago O'Hare Intl) is currently priced at $194.

  • Can I find deals for flights from Wilmington to Chicago that include hotel bookings?

    Yes. In addition to deals on Wilmington to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wilmington to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wilmington to Chicago.

  • Can I find deals for business class flights from Wilmington to Chicago?

    Yes. Cheapflights offers flight deals from Wilmington to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wilmington to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Wilmington to Chicago (average of $98). Flying from Wilmington to Chicago in February is currently the most expensive (average of $228). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Top 2 airlines flying from Wilmington to Chicago

Discover the top 2 airlines that operate flights from Wilmington to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$314FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$249Average$333FlexibilityNo cancel feeOn-time69%

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