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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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Find 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 October 16, 2025.

This United Airlines deal was found by Cheapflights users on 10/16. 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 11/75:45 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Tue 11/1110:43 amORD - CRW
Nonstop1h 41mUnited Airlines
Deal found 10/16$179
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Sat 11/16:00 amCRW - ORD
1 stop7h 03mAmerican Airlines
Sun 11/25:00 amORD - CRW
1 stop4h 40mAmerican Airlines
Deal found 10/15$208
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/317:36 pmCRW - ORD
2 stops28h 53mMultiple Airlines
Wed 11/57:34 pmORD - CRW
1 stop17h 29mMultiple Airlines
Deal found 10/15$229
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Wed 10/295:45 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Sun 11/210:40 amORD - CRW
Nonstop1h 43mUnited Airlines
Deal found 10/14$239
This Delta deal was found by Cheapflights users on 10/14. 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 12/46:50 pmCRW - MDW
1 stop5h 59mDelta
Sun 12/75:13 pmMDW - CRW
1 stop4h 36mDelta
Deal found 10/14$243
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 11/121:59 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Thu 11/1310:43 amORD - CRW
Nonstop1h 41mUnited Airlines
Deal found 10/15$247
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 10/295:45 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Sat 11/12:25 pmORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 10/15$249
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/302:43 pmCRW - MDW
1 stop18h 49mMultiple Airlines
Mon 11/36:30 amMDW - CRW
2 stops11h 26mMultiple Airlines
Deal found 10/15$251
This Delta deal was found by Cheapflights users on 10/15. 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 10/246:48 pmCRW - ORD
1 stop6h 10mDelta
Sun 10/265:20 amORD - CRW
1 stop4h 23mDelta
Deal found 10/15$258
This United Airlines deal was found by Cheapflights users on 10/15. 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 10/315:45 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Wed 11/52:25 pmORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 10/15$263
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/79:58 amCRW - ORD
2 stops37h 26mMultiple Airlines
Thu 12/112:18 pmORD - CRW
1 stop27h 38mMultiple Airlines
Deal found 10/16$264
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 11/127:06 pmCRW - ORD
1 stop5h 31mAmerican Airlines
Thu 11/135:00 amORD - CRW
1 stop4h 40mAmerican Airlines
Deal found 10/15$266

Cheap 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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$178
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$351

Good round-trip deal

$307 or less

Good one-way deal

$337 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. 15% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 16, 2025.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Fly from

Charleston

Fly to

Chicago

Route

Depart

Return

Price

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 11/7

5:45 pm-6:41 pm

Nonstop1h 56m

Chicago O'Hare Intl

Tue 11/11

10:43 am-1:24 pm

Nonstop1h 41m

$179

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/31

7:36 pm-11:29 pm

2 stops28h 53m

Chicago O'Hare Intl

Wed 11/5

7:34 pm-2:03 pm

1 stop17h 29m

$229

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 10/29

5:45 pm-6:41 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 11/2

10:40 am-1:23 pm

Nonstop1h 43m

$239

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 12/4

6:50 pm-11:49 pm

1 stop5h 59m

Chicago Midway

Sun 12/7

5:13 pm-10:49 pm

1 stop4h 36m

$243

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 11/12

1:59 pm-2:55 pm

Nonstop1h 56m

Chicago O'Hare Intl

Thu 11/13

10:43 am-1:24 pm

Nonstop1h 41m

$247

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 10/29

5:45 pm-6:41 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sat 11/1

2:25 pm-5:10 pm

Nonstop1h 45m

$249

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 10/30

2:43 pm-8:32 am

1 stop18h 49m

Chicago Midway

Mon 11/3

6:30 am-6:56 pm

2 stops11h 26m

$251

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/31

5:45 pm-6:41 pm

Nonstop1h 56m

Chicago O'Hare Intl

Wed 11/5

2:25 pm-5:10 pm

Nonstop1h 45m

$263

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sun 12/7

9:58 am-10:24 pm

2 stops37h 26m

Chicago O'Hare Intl

Thu 12/11

2:18 pm-6:56 pm

1 stop27h 38m

$264

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 11/12

7:06 pm-11:37 pm

1 stop5h 31m

Chicago O'Hare Intl

Thu 11/13

5:00 am-10:40 am

1 stop4h 40m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 26 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $180). Flying from Charleston, West Virginia to Chicago in February is currently the most expensive (average of $286). 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 October 16, 2025.

It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 39% 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 October 16, 2025.

The most flights from CRW to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

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

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 16, 2025.
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
8,982 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

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
8,982 reviews
United Airlines
7.4
Good
8,982 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

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 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. 2 airlines 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 $179, United Airlines can have you in Chicago from Charleston, West Virginia in 1h 56m. 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 are the cheapest airlines flying from Charleston, West Virginia to Chicago round-trip?

    Currently priced at $179, 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. Check Cheapflights for deals on American Airlines for as low as $198. United Airlines is currently priced 48% 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 (84%), SkyWest Airlines (70%) and United Airlines (70%).

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

    While on average a flight from Charleston, West Virginia to Chicago is generally $431, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Charleston Yeager - Chicago O'Hare Intl), you can expect to pay $184 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, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $180). Flying from Charleston, West Virginia to Chicago in February is currently the most expensive (average of $286). 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
Chesterton

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Alternative routes for Charleston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Charleston to Chicago

Discover the top 2 airlines 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$310FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$303FlexibilityNo cancel feeOn-time71%

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