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$168+ Cheap flights from Charleston, WV (CRW) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
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 julio 29, 2025.

Round-trip from

$168
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$510

Good round-trip deal

$416 or less

Good one-way deal

$273 or less
From Charleston Yeager to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 29, 2025.

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.
vie. 9/125:38 pmCRW - ORD
1 stop6h 34mAmerican Airlines
sáb. 9/133:33 pmORD - CRW
1 stop5h 55mAmerican Airlines
Deal found 7/27$168
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/205:45 pmCRW - ORD
Nonstop1h 54mUnited Airlines
sáb. 9/2710:40 amORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 7/28$179
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.
sáb. 9/1311:22 amCRW - ORD
2 stops11h 08mDelta
mié. 9/175:30 amORD - CRW
1 stop4h 12mDelta
Deal found 7/27$204
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.
vie. 9/123:25 pmCRW - MDW
1 stop7h 11mDelta
sáb. 9/134:31 pmMDW - CRW
1 stop5h 09mDelta
Deal found 7/28$263

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 julio 29, 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

vie. 9/12

5:38 pm-11:12 pm

1 stop6h 34m

Chicago O'Hare Intl

sáb. 9/13

3:33 pm-10:28 pm

1 stop5h 55m

$168

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

sáb. 9/20

5:45 pm-6:39 pm

Nonstop1h 54m

Chicago O'Hare Intl

sáb. 9/27

10:40 am-1:25 pm

Nonstop1h 45m

$179

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

sáb. 9/13

11:22 am-9:30 pm

2 stops11h 08m

Chicago O'Hare Intl

mié. 9/17

5:30 am-10:42 am

1 stop4h 12m

$204

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

vie. 9/12

3:25 pm-9:36 pm

1 stop7h 11m

Chicago Midway

sáb. 9/13

4:31 pm-10:40 pm

1 stop5h 09m

$263

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

dom. 10/5

6:30 am-9:40 am

1 stop4h 10m

$218

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

dom. 10/5

4:01 pm-9:21 pm

1 stop6h 20m

$218

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

dom. 10/5

7:00 am-7:54 am

Nonstop1h 54m

$239

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

dom. 10/5

6:30 am-12:42 pm

2 stops7h 12m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 julio 29, 2025.

It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 17% on the cost of your flight, compared to a flight at noon.

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 julio 29, 2025.
Read through reviews of airlines operating flights from Charleston to Chicago, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
8,899 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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 5 outbound flights to Chicago per day.

  • What are the cheapest airlines flying from Charleston, West Virginia to Chicago round-trip?

    Currently priced at $168, American Airlines will fly you from Charleston, West Virginia to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Delta - these airlines can fly you to your destination from $179 and $204, respectively. American Airlines is currently priced 53% 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 Delta. According to our data, you can fly for as low as $218. Users have also found prices from $218 and $239 on American Airlines 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 (84%), SkyWest Airlines (77%) and United Airlines (77%).

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

    While on average a flight from Charleston, West Virginia to Chicago is generally $2,094, our data shows the cheapest flight currently is $209. 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
Valparaiso
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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$309FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$303FlexibilityNo cancel feeOn-time71%

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