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$178+ Cheap flights from Charleston, WV (CRW) 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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Cheap flight deals from Charleston to Chicago

Cheapest flights from Charleston to Chicago
Explore the most affordable flight options available from Charleston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2026.

This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2010:45 am
CRW
-
ORD
Nonstop2h 00m
United Airlines
Sat 8/227:00 am
ORD
-
CRW
Nonstop1h 54m
United Airlines
Deal found 7/26$249
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:00 am
CRW
-
ORD
Nonstop1h 57m
United Airlines
Mon 9/216:30 am
ORD
-
CRW
Nonstop1h 52m
United Airlines
Deal found 7/27$262
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:00 am
CRW
-
ORD
Nonstop2h 00m
United Airlines
Sun 9/206:30 am
ORD
-
CRW
Nonstop1h 52m
United Airlines
Deal found 7/26$264
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:07 am
CRW
-
MDW
1 stop6h 08m
Delta
Sat 8/224:39 pm
MDW
-
CRW
1 stop4h 21m
Delta
Deal found 7/26$268
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:52 pm
CRW
-
ORD
1 stop4h 57m
Delta
Mon 8/313:25 pm
ORD
-
CRW
1 stop7h 06m
Delta
Deal found 7/28$268
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:05 pm
CRW
-
ORD
Nonstop2h 00m
United Airlines
Sun 9/67:00 am
ORD
-
CRW
Nonstop1h 54m
United Airlines
Deal found 7/29$269
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:50 pm
CRW
-
MDW
1 stop4h 46m
Delta
Sat 8/291:25 pm
MDW
-
CRW
2 stops7h 35m
Delta
Deal found 7/27$274
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:50 pm
CRW
-
ORD
1 stop6h 07m
Delta
Sat 8/296:59 am
ORD
-
CRW
2 stops7h 55m
Delta
Deal found 7/28$274
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:14 pm
CRW
-
ORD
1 stop5h 43m
American Airlines
Sun 8/166:49 am
ORD
-
CRW
1 stop7h 11m
American Airlines
Deal found 7/27$283
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/112:35 pm
CRW
-
ORD
1 stop5h 27m
Delta
Thu 12/35:30 am
ORD
-
CRW
1 stop7h 25m
Delta
Deal found 7/29$288
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:33 pm
CRW
-
ORD
2 stops6h 57m
Delta
Mon 9/285:30 am
ORD
-
CRW
1 stop7h 23m
Delta
Deal found 7/28$289
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:02 am
CRW
-
ORD
Nonstop1h 57m
United Airlines
Mon 8/319:10 pm
ORD
-
CRW
Nonstop1h 49m
United Airlines
Deal found 7/26$291

Find flight deals from Charleston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CRW) 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 July 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(United Airlines)

One-way from

$178
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$482

Good round-trip deal

$430 or less

Good one-way deal

$389 or less
Provider with most accurate pricing for Charleston Yeager-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charleston Yeager-Chicago (CHI) flights.
Search Deals
From Charleston Yeager to Chicago (CHI)
Search Deals
One-way flight from Charleston Yeager to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Charleston Yeager to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Charleston Yeager to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston 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 July 30, 2026.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 9/25

6:05 pm-7:03 pm

Nonstop1h 58m

Chicago O'Hare Intl

Mon 9/28

6:51 am-9:43 am

Nonstop1h 52m

$249

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 8/20

10:45 am-11:45 am

Nonstop2h 00m

Chicago O'Hare Intl

Sun 8/23

7:00 am-9:54 am

Nonstop1h 54m

$249

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 9/10

10:00 am-11:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Thu 9/17

6:30 am-9:22 am

Nonstop1h 52m

$249
Quickest round-trip

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 9/16

6:05 pm-7:02 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/20

6:30 am-9:22 am

Nonstop1h 52m

$249

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 10/2

6:54 pm-10:44 pm

1 stop4h 50m

Chicago Midway

Mon 10/5

6:05 am-1:53 pm

1 stop6h 48m

$268

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 8/20

11:07 am-4:15 pm

1 stop6h 08m

Chicago Midway

Sat 8/22

4:39 pm-10:00 pm

1 stop4h 21m

$268

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 8/26

6:50 pm-10:36 pm

1 stop4h 46m

Chicago Midway

Sat 8/29

1:25 pm-10:00 pm

2 stops7h 35m

$274

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 9/17

6:54 pm-10:45 pm

1 stop4h 51m

Chicago Midway

Mon 9/21

1:19 pm-11:20 pm

2 stops9h 01m

$274

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 9/25

6:54 pm-10:44 pm

1 stop4h 50m

Chicago Midway

Mon 9/28

1:19 pm-11:20 pm

2 stops9h 01m

$274

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 10/21

6:00 am-12:13 pm

1 stop7h 13m

Chicago O'Hare Intl

Sat 10/24

11:19 am-10:17 pm

2 stops9h 58m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 34 resultsSorted by cheapest first
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3
4

Compare providers for flights from Charleston 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 Charleston to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 Charleston, West Virginia-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charleston, West Virginia-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charleston, West Virginia-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charleston, West Virginia-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 Charleston, West Virginia-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 Charleston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Charleston 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 Charleston to Chicago

What is the cheapest month to book a flight from Charleston, West Virginia to Chicago?

Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $269). Flying from Charleston, West Virginia to Chicago in November is currently the most expensive (average of $379). 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 CRW to CHI?

Find hourly flight availability from Charleston 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 July 30, 2026.

It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 18% on the cost of your flight, compared to a flight in the morning.

Weekly flight availability from Charleston, West Virginia to Chicago

Explore weekly flight availability from Charleston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 30, 2026.

The most flights from CRW to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Charleston, West Virginia to Chicago?

Airfare is typical for this route at the moment.
Charleston, West Virginia to Chicago flights typically cost between $238 and $401 in August.
The cheapest round-trip price found within the last 5 days was $249 on United Airlines (Aug 20-Aug 22).

What is the cheapest day to fly from Charleston, West Virginia to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Charleston to Chicago. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Charleston, West Virginia to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday evenings 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 July 30, 2026.
Read through reviews of airlines operating flights from Charleston to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,046 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,046 reviews
United Airlines
7.4
Good
10,046 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Charleston 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 Charleston to Chicago?

    Charleston Yeager (CRW), located 2.7 mi from the city center, is the airport you fly out of when you book flights from Charleston to Chicago. 1 airline have flights from Yeager to Chicago on a regular basis. Booking flights from Charleston Yeager to Chicago should not be difficult; the airport handles an average of 7 outbound flights to Chicago per day.

  • How long is the flight from Charleston, West Virginia to Chicago?

    For as low as $249, United Airlines can have you in Chicago from Charleston, West Virginia in 2h. Charleston, West Virginia and Chicago are separated by a distance of 416 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Charleston, West Virginia to Chicago round-trip?

    Currently priced at $190, United Airlines will fly you from Charleston, West Virginia to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. United Airlines is currently priced 38% below the average price you’ll pay for this route.

  • What are the most popular routes from Charleston, West Virginia to Chicago?

    While some choose either Charleston Yeager - Chicago Midway or Charleston Yeager - Chicago Greater Rockford, Charleston Yeager - Chicago O'Hare Intl is the most popular route from Charleston, West Virginia to Chicago.

  • What are the most reliable airlines from Charleston, West Virginia to Chicago?

    The top 3 most reliable airlines when flying from Charleston, West Virginia to Chicago are ANA (72%), SkyWest Airlines (69%) and United Airlines (69%).

  • What are the cheapest flights from Charleston, West Virginia to Chicago?

    While on average a flight from Charleston, West Virginia to Chicago is generally $1,268, our data shows the cheapest flight currently is $223. When looking at the most popular route, (Charleston Yeager - Chicago O'Hare Intl), you can expect to pay $249 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Charleston 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 Charleston, West Virginia to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $269). Flying from Charleston, West Virginia to Chicago in November is currently the most expensive (average of $379). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top airline flying from Charleston to Chicago

Discover the top airline that operate flights from Charleston 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 July 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$190Average$328FlexibilityNo cancel feeOn-time69%

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