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$79+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:30 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Mon 12/155:51 pmORD - CRW
Nonstop1h 41mUnited Airlines
Deal found 10/28$179
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 11/111:59 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Sat 11/152:25 pmORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 10/27$189
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:08 pmCRW - ORD
1 stop5h 50mAmerican Airlines
Mon 12/153:52 pmORD - CRW
1 stop5h 01mAmerican Airlines
Deal found 10/28$198
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 11/117:45 amCRW - ORD
1 stop5h 43mAmerican Airlines
Sat 11/155:00 amORD - CRW
1 stop4h 40mAmerican Airlines
Deal found 10/27$208
This United Airlines deal was found by Cheapflights users on 10/28. 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 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 10/28$219
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:06 pmCRW - ORD
1 stop5h 31mAmerican Airlines
Tue 11/115:00 amORD - CRW
1 stop5h 50mAmerican Airlines
Deal found 10/28$238
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/272:43 pmCRW - ORD
1 stop9h 23mMultiple Airlines
Thu 12/411:44 amORD - CRW
2 stops30h 12mMultiple Airlines
Deal found 10/28$244
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 11/181:59 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Sat 11/222:25 pmORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 10/26$249
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:59 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Thu 12/45:51 pmORD - CRW
Nonstop1h 41mUnited Airlines
Deal found 10/28$254
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/186:00 amCRW - ORD
1 stop7h 04mDelta
Sat 11/225:23 amORD - CRW
1 stop4h 15mDelta
Deal found 10/26$263
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/285:45 pmCRW - ORD
Nonstop1h 56mUnited Airlines
Tue 11/182:25 pmORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 10/28$279
This Delta deal was found by Cheapflights users on 10/28. 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 11/74:05 pmCRW - MDW
1 stop7h 09mDelta
Tue 11/1112:47 pmMDW - CRW
1 stop4h 23mDelta
Deal found 10/28$338

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 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$79
(Delta)

Popular in

December

Cheapest in

February

Average price

$334

Good round-trip deal

$327 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. 13% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 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 28, 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

Wed 2/18

6:40 pm-11:54 pm

1 stop6h 14m

Chicago O'Hare Intl

Sat 2/21

9:30 am-3:12 pm

1 stop4h 42m

$183

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 11/11

1:59 pm-2:55 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sat 11/15

2:25 pm-5:10 pm

Nonstop1h 45m

$189

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 12/13

1:08 pm-5:58 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 12/15

3:52 pm-9:53 pm

1 stop5h 01m

$198

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Sat 2/21

12:02 pm-3:25 pm

1 stop4h 23m

Chicago Midway

Wed 2/25

5:25 pm-10:34 pm

1 stop4h 09m

$208

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 11/11

7:45 am-12:28 pm

1 stop5h 43m

Chicago O'Hare Intl

Sat 11/15

5:00 am-10:40 am

1 stop4h 40m

$208

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

$219

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 4/9

2:05 pm-2:53 pm

Nonstop1h 48m

Chicago O'Hare Intl

Mon 4/13

5:56 pm-8:37 pm

Nonstop1h 41m

$231

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 2/18

6:45 am-7:50 am

Nonstop2h 05m

Chicago O'Hare Intl

Sat 2/21

6:20 pm-9:08 pm

Nonstop1h 48m

$239

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 11/27

2:43 pm-11:06 pm

1 stop9h 23m

Chicago O'Hare Intl

Thu 12/4

11:44 am-6:56 pm

2 stops30h 12m

$244

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Fri 11/7

4:05 pm-10:14 pm

1 stop7h 09m

Chicago Midway

Tue 11/11

12:47 pm-6:10 pm

1 stop4h 23m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 30 results
1
2
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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*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 Charleston, West Virginia-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Charleston, West Virginia-Chicago flight deals on Cheapflights vs. eDreams >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 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 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 28, 2025.

It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the morning.

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 28, 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
9,001 reviews

Overall

7.4

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,001 reviews
United Airlines
7.4
Good
9,001 reviews

Overall

7.4

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 4 outbound flights to Chicago per day.

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

    For as low as $189, Delta 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 47% 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 $458, our data shows the cheapest flight currently is $239. When looking at the most popular route, (Charleston Yeager - Chicago O'Hare Intl), you can expect to pay $183 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

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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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$313FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$303FlexibilityNo cancel feeOn-time71%

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