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$130+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
May 17 — May 241
Sat 5/17
Sat 5/24
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 May 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Priceline
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$130
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$338

Good round-trip deal

$393 or less

Good one-way deal

$274 or less
Provider with most accurate pricing for Charleston Yeager-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Charleston Yeager-Chicago (CHI) flights.
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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. 8% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 12, 2025.

This United Airlines deal was found by Cheapflights users on 5/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/105:16 pmCRW - ORD
Nonstop1h 54mUnited Airlines
Tue 6/176:05 pmORD - CRW
Nonstop1h 44mUnited Airlines
Deal found 5/11$179
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 6/33:32 pmCRW - MDW
1 stop6h 55mDelta
Tue 6/106:00 amMDW - CRW
1 stop7h 20mDelta
Deal found 5/11$198
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 6/36:59 pmCRW - ORD
1 stop5h 59mDelta
Tue 6/107:10 amORD - CRW
1 stop6h 10mDelta
Deal found 5/11$198
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Fri 6/2010:59 amCRW - ORD
1 stop5h 49mAmerican Airlines
Sun 6/225:29 amORD - CRW
1 stop3h 57mAmerican Airlines
Deal found 5/11$268
This Mytrip deal was found by Cheapflights users on 5/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/12:29 pmCRW - ORD
2 stops19h 21mMultiple Airlines
Sat 7/57:56 amORD - CRW
2 stops26h 04mMultiple Airlines
Deal found 5/11$579

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 May 12, 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

Tue 6/10

5:16 pm-6:10 pm

Nonstop1h 54m

Chicago O'Hare Intl

Tue 6/17

6:05 pm-8:49 pm

Nonstop1h 44m

$179

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Tue 6/3

3:32 pm-9:27 pm

1 stop6h 55m

Chicago Midway

Tue 6/10

6:00 am-2:20 pm

1 stop7h 20m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 8/20

6:24 am-12:09 pm

1 stop6h 45m

Chicago O'Hare Intl

Sat 8/23

9:30 am-2:44 pm

1 stop4h 14m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 8/19

8:14 am-2:09 pm

1 stop6h 55m

Chicago O'Hare Intl

Mon 8/25

5:20 am-10:33 am

1 stop4h 13m

$258

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 5/27

2:31 pm-6:42 am

3 stops41h 11m

Chicago O'Hare Intl

Sat 5/31

1:59 pm-11:00 am

1 stop20h 01m

$416

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 6/24

5:30 am-10:42 am

1 stop6h 12m

$130

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 6/26

7:00 pm-11:58 pm

1 stop5h 58m

$173

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 6/24

1:55 pm-2:45 pm

Nonstop1h 50m

$239

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 6/26

11:40 am-1:36 pm

3 stops26h 56m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 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 Priceline the most. Priceline 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, 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 May 12, 2025.

It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 14% 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 May 12, 2025.

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 12, 2025.
To help decide which airline to fly from Charleston to Chicago, see what other customers have to say about Delta, United Airlines and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,724 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 8 outbound flights to Chicago per day.

  • 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. Search Cheapflights for deals from Delta and American Airlines - these airlines can fly you to your destination from $198 and $263, respectively. United Airlines is currently priced 51% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Charleston, West Virginia to Chicago one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $130. Users have also found prices from $173 and $239 on Delta and United Airlines, respectively.

  • 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 (78%), Air New Zealand (73%) and SkyWest 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 $896, our data shows the cheapest flight currently is $150. 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 Charleston?

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

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Alternative routes for Charleston to Chicago

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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 May 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$178Average$303FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$180Average$313FlexibilityNo cancel feeOn-time69%

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