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$183+ 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$183
(United Airlines)

Popular in

July

Cheapest in

February

Average price

$320

Good round-trip deal

$398 or less

Good one-way deal

$314 or less
From Charleston Yeager to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/11. 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.
sáb. 7/191:55 pmCRW - ORD
Nonstop1h 54mUnited Airlines
mié. 7/232:00 pmORD - CRW
Nonstop1h 45mUnited Airlines
Deal found 6/11$183
This American Airlines deal was found by Cheapflights users on 6/11. 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.
sáb. 6/145:41 amCRW - ORD
1 stop6h 00mAmerican Airlines
dom. 6/155:29 amORD - CRW
1 stop3h 57mAmerican Airlines
Deal found 6/11$188
This Delta deal was found by Cheapflights users on 6/10. 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.
vie. 9/123:25 pmCRW - MDW
1 stop7h 19mDelta
mié. 9/175:25 pmMDW - CRW
1 stop4h 09mDelta
Deal found 6/10$218
This Delta deal was found by Cheapflights users on 6/10. 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.
sáb. 7/195:43 pmCRW - ORD
1 stop7h 26mDelta
mar. 7/229:00 amORD - CRW
2 stops8h 01mDelta
Deal found 6/10$224
This Mytrip deal was found by Cheapflights users on 6/11. 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.
dom. 7/2011:40 amCRW - ORD
1 stop6h 01mMultiple Airlines
mié. 7/2310:00 amORD - CRW
2 stops24h 00mMultiple Airlines
Deal found 6/11$370
This Mytrip deal was found by Cheapflights users on 6/11. 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.
jue. 6/269:49 amCRW - MDW
2 stops29h 14mMultiple Airlines
lun. 6/3010:34 amMDW - CRW
2 stops21h 35mMultiple Airlines
Deal found 6/11$591

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 junio 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

sáb. 7/19

1:55 pm-2:49 pm

Nonstop1h 54m

Chicago O'Hare Intl

mié. 7/23

2:00 pm-4:45 pm

Nonstop1h 45m

$183

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

lun. 7/7

5:30 am-11:50 am

1 stop7h 20m

Chicago O'Hare Intl

jue. 7/10

5:15 am-10:30 am

1 stop4h 15m

$188

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

vie. 9/12

3:25 pm-9:44 pm

1 stop7h 19m

Chicago Midway

mié. 9/17

5:25 pm-10:34 pm

1 stop4h 09m

$218

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

sáb. 7/19

5:43 pm-12:09 am

1 stop7h 26m

Chicago O'Hare Intl

mar. 7/22

9:00 am-6:01 pm

2 stops8h 01m

$224

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

dom. 7/20

11:40 am-4:41 pm

1 stop6h 01m

Chicago O'Hare Intl

mié. 7/23

10:00 am-11:00 am

2 stops24h 00m

$370

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

jue. 6/26

9:49 am-2:03 pm

2 stops29h 14m

Chicago Midway

lun. 6/30

10:34 am-9:09 am

2 stops21h 35m

$591

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 junio 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 16% 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 junio 12, 2025.

The most flights from CRW to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (6 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 junio 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

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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 7 outbound flights to Chicago per day.

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

    Currently priced at $183, 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 American Airlines and Delta - these airlines can fly you to your destination from $188 and $218, respectively. 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 (86%), SkyWest Airlines (83%) and United Airlines (83%).

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

    While on average a flight from Charleston, West Virginia to Chicago is generally $1,157, our data shows the cheapest flight currently is $208. 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, 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
Lansing
Benton Harbor
Porter
Hammond
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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$178Average$303FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$312FlexibilityNo cancel feeOn-time69%

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