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$84+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$168
(Delta)

One-way from

$84
(Delta)

Popular in

December

Cheapest in

February

Average price

$399

Good round-trip deal

$370 or less

Good one-way deal

$258 or less
From Charleston Yeager to Chicago (CHI)
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One-way flight from Charleston Yeager to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Charleston Yeager to Chicago (CHI).
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Price to beat on a one-way flight from Charleston Yeager to Chicago (CHI).
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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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 10/36:54 pmCRW - ORD
1 stop6h 00mDelta
Sat 10/45:30 amORD - CRW
1 stop4h 12mDelta
Deal found 9/10$168
This Delta deal was found by Cheapflights users on 9/11. 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 9/266:54 pmCRW - ORD
1 stop6h 00mDelta
Tue 9/305:30 amORD - CRW
1 stop4h 12mDelta
Deal found 9/11$178
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/28:07 pmCRW - ORD
1 stop4h 32mAmerican Airlines
Sun 10/55:00 amORD - CRW
1 stop4h 25mAmerican Airlines
Deal found 9/10$198
This American Airlines deal was found by Cheapflights users on 9/11. 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 9/275:38 pmCRW - ORD
1 stop6h 34mAmerican Airlines
Fri 10/173:11 pmORD - CRW
1 stop5h 23mAmerican Airlines
Deal found 9/11$208
This Delta deal was found by Cheapflights users on 9/10. 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 10/36:54 pmCRW - ORD
1 stop6h 00mDelta
Sun 10/55:30 amORD - CRW
1 stop4h 12mDelta
Deal found 9/10$213
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/27:00 amCRW - ORD
Nonstop1h 54mUnited Airlines
Sat 10/46:31 pmORD - CRW
Nonstop1h 55mUnited Airlines
Deal found 9/10$239
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/82:00 pmCRW - ORD
Nonstop1h 54mUnited Airlines
Fri 10/102:10 pmORD - CRW
Nonstop1h 50mUnited Airlines
Deal found 9/10$247
This United Airlines deal was found by Cheapflights users on 9/10. 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 9/255:38 pmCRW - ORD
Nonstop1h 59mUnited Airlines
Mon 9/2910:40 amORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 9/10$249
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/25:38 pmCRW - ORD
Nonstop1h 52mUnited Airlines
Sun 10/56:31 pmORD - CRW
Nonstop1h 55mUnited Airlines
Deal found 9/10$257
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/28:07 pmCRW - ORD
1 stop4h 32mAmerican Airlines
Sat 10/45:08 pmORD - CRW
1 stop5h 07mAmerican Airlines
Deal found 9/10$258
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 9/255:35 amCRW - ORD
1 stop6h 31mAmerican Airlines
Fri 10/173:11 pmORD - CRW
1 stop5h 23mAmerican Airlines
Deal found 9/11$268
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/95:35 pmCRW - ORD
Nonstop1h 59mUnited Airlines
Fri 10/102:10 pmORD - CRW
Nonstop1h 50mUnited Airlines
Deal found 9/10$269

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 September 11, 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 9/26

6:54 pm-11:54 pm

1 stop6h 00m

Chicago O'Hare Intl

Tue 9/30

5:30 am-10:42 am

1 stop4h 12m

$178

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 9/25

7:00 am-7:54 am

Nonstop1h 54m

Chicago O'Hare Intl

Sun 9/28

10:40 am-1:25 pm

Nonstop1h 45m

$189

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 10/2

8:07 pm-11:39 pm

1 stop4h 32m

Chicago O'Hare Intl

Sun 10/5

5:00 am-10:25 am

1 stop4h 25m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/3

5:35 am-12:02 pm

1 stop7h 27m

Chicago O'Hare Intl

Sun 10/5

5:00 am-10:25 am

1 stop4h 25m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 11/8

7:51 pm-11:58 pm

1 stop5h 07m

Chicago O'Hare Intl

Sat 11/15

4:08 pm-9:45 pm

1 stop4h 37m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/17

5:35 pm-6:34 pm

Nonstop1h 59m

Chicago O'Hare Intl

Sun 10/19

6:31 pm-9:26 pm

Nonstop1h 55m

$206

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/3

6:54 pm-11:54 pm

1 stop6h 00m

Chicago O'Hare Intl

Sun 10/5

5:30 am-10:42 am

1 stop4h 12m

$213

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 10/2

2:00 pm-2:54 pm

Nonstop1h 54m

Chicago O'Hare Intl

Sun 10/5

6:31 pm-9:26 pm

Nonstop1h 55m

$229

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/3

5:38 pm-6:37 pm

Nonstop1h 59m

Chicago O'Hare Intl

Sat 10/4

6:31 pm-9:26 pm

Nonstop1h 55m

$239

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 10/2

7:00 am-7:54 am

Nonstop1h 54m

Chicago O'Hare Intl

Sat 10/4

6:31 pm-9:26 pm

Nonstop1h 55m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 27 results
1
2
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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, August is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $245). Flying from Charleston, West Virginia to Chicago in March is currently the most expensive (average of $321). 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 September 11, 2025.

It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight at noon.

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 September 11, 2025.

The most flights from CRW to CHI are scheduled on a Monday (7 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 September 11, 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
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

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
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

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. 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 6 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 54m. 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 49% 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 (79%), SkyWest Airlines (64%) and United Airlines (64%).

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

    While on average a flight from Charleston, West Virginia to Chicago is generally $676, our data shows the cheapest flight currently is $219. When looking at the most popular route, (Charleston Yeager - Chicago O'Hare Intl), you can expect to pay $179 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, August is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $245). Flying from Charleston, West Virginia to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$303FlexibilityNo cancel feeOn-time71%

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