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$64+ Cheap flights from West Virginia 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from West Virginia to Chicago

Keep the following information in mind while searching for West Virginia to Chicago flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Southwest)

One-way from

$64
(Southwest)

Popular in

December

Cheapest in

February

Average price

$321

Good round-trip deal

$290 or less

Good one-way deal

$337 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 West Virginia to Chicago (CHI)
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One-way flight from West Virginia to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from West Virginia to Chicago (CHI).
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Price to beat on a one-way flight from West Virginia to Chicago (CHI).
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Find flight deals from West Virginia to Chicago

Cheapest flights from West Virginia to Chicago
Explore the most affordable flight options available from West Virginia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amPIT - MDW
1 stop4h 40mSouthwest
Wed 12/31:30 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 10/31$127
This Priceline deal was found by Cheapflights users on 10/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:30 pmPIT - ORD
1 stop7h 45mFrontier
Mon 11/178:26 amORD - PIT
1 stop4h 27mFrontier
Deal found 10/31$127
This Priceline deal was found by Cheapflights users on 10/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:05 pmPIT - ORD
1 stop8h 04mSpirit Airlines
Thu 12/113:26 pmORD - PIT
1 stop8h 15mSpirit Airlines
Deal found 10/31$135
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amPIT - ORD
1 stop7h 15mSouthwest
Wed 12/31:45 pmORD - PIT
1 stop6h 20mSouthwest
Deal found 10/31$137
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:14 pmPIT - ORD
1 stop13h 13mSpirit Airlines
Wed 11/1910:52 amORD - PIT
1 stop9h 19mSpirit Airlines
Deal found 11/2$138
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/118:15 amPIT - ORD
Nonstop1h 57mAmerican Airlines
Thu 12/186:30 pmORD - PIT
Nonstop1h 30mAmerican Airlines
Deal found 10/30$139
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:19 pmIAD - ORD
1 stop6h 05mFrontier
Sun 12/76:11 amORD - IAD
1 stop9h 13mFrontier
Deal found 11/2$141
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 11/1$141
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Fri 11/1410:06 pmPIT - ORD
1 stop15h 39mMultiple Airlines
Mon 11/177:34 pmORD - PIT
2 stops24h 37mMultiple Airlines
Deal found 10/31$145
This Priceline deal was found by Cheapflights users on 10/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:30 pmPIT - ORD
1 stop7h 45mFrontier
Sun 11/165:11 amORD - PIT
1 stop7h 42mFrontier
Deal found 10/31$146
This Priceline deal was found by Cheapflights users on 11/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:26 pmIAD - ORD
1 stop5h 58mFrontier
Sat 12/131:24 pmORD - IAD
1 stop8h 41mFrontier
Deal found 11/2$146
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 12/55:19 pmIAD - ORD
1 stop6h 05mMultiple Airlines
Sun 12/712:09 pmORD - IAD
1 stop7h 15mMultiple Airlines
Deal found 11/2$148

Cheapflights Fare Finder

 
Customize your flight search to find flights from West Virginia 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 November 2, 2025.
Use the filters below to find and compare flights from West Virginia to Chicago that are best for you.

Fly from

West Virginia

Fly to

Chicago

Route

Depart

Return

Price

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/29

6:00 am-1:10 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 2/2

2:05 pm-11:53 pm

1 stop8h 48m

$155

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/22

6:00 am-1:10 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 1/26

2:05 pm-11:53 pm

1 stop8h 48m

$155

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Mon 11/24

11:43 am-4:39 pm

1 stop5h 56m

Chicago Midway

Thu 11/27

5:34 pm-12:21 am

1 stop5h 47m

$157

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 12/11

10:53 am-2:59 pm

1 stop5h 06m

Chicago O'Hare Intl

Thu 12/18

5:30 am-12:41 pm

1 stop6h 11m

$157

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 12/18

6:00 am-12:10 pm

1 stop7h 10m

Chicago O'Hare Intl

Thu 12/18

6:04 pm-12:12 am

1 stop5h 08m

$157

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 11/26

6:40 pm-7:31 pm

Nonstop1h 51m

Chicago O'Hare Intl

Wed 12/3

6:30 pm-9:00 pm

Nonstop1h 30m

$163

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 11/22

8:38 pm-9:01 am

1 stop13h 23m

Chicago O'Hare Intl

Mon 11/24

11:48 am-7:21 am

1 stop18h 33m

$166

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 11/19

10:06 pm-12:56 pm

1 stop15h 50m

Chicago O'Hare Intl

Wed 12/3

10:12 am-9:47 pm

1 stop10h 35m

$177

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 11/24

6:00 am-10:36 am

1 stop5h 36m

Chicago O'Hare Intl

Thu 11/27

1:15 pm-3:53 pm

Nonstop1h 38m

$178

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Mon 11/24

1:59 pm-2:55 pm

Nonstop1h 56m

Chicago O'Hare Intl

Wed 12/3

2:10 pm-4:55 pm

Nonstop1h 45m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 60 results
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Best time to book a flight from West Virginia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from West Virginia 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 West Virginia to Chicago

What is the cheapest month to book a flight from West Virginia to Chicago?

Currently, September is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $180). Flying from West Virginia to Chicago in August is currently the most expensive (average of $279). 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 WV to CHI?

Find hourly flight availability from West Virginia 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 November 2, 2025.

When flying from West Virginia to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 52% versus a flight at noon.

Weekly flight availability from West Virginia to Chicago

Explore weekly flight availability from West Virginia 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 November 2, 2025.

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

How much does it cost to fly round-trip from West Virginia to Chicago?

Related info for your journey

Find useful and relevant information for your journey from West Virginia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    JetBlue, Delta, and American Airlines can get you from West Virginia to Chicago in just under 1h 51m. Your travel time can differ by up to 6h 19m. Airlines will cover a distance of 411 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 to fly from West Virginia to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $64. Users have also found prices from $65 and $79 on United Airlines and Frontier, respectively.

  • What are the most popular routes from West Virginia to Chicago?

    When deciding which route to take from West Virginia to Chicago consider Washington, D.C. Dulles Intl - Chicago O'Hare Intl, Washington, D.C. Dulles Intl - Chicago Midway or Pittsburgh - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from West Virginia to Chicago?

    No one likes to see their flight delayed. When booking a flight from West Virginia to Chicago consider choosing ANA (84%), SkyWest Airlines (70%) or United Airlines (70%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from West Virginia to Chicago is $243. On average you can expect to pay $478. The most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), can usually be booked for $110.

  • Can I find deals for flights from West Virginia to Chicago that include hotel bookings?

    Yes. In addition to deals on West Virginia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from West Virginia to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from West Virginia to Chicago.

  • Can I find deals for business class flights from West Virginia to Chicago?

    Yes. Cheapflights offers flight deals from West Virginia 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 West Virginia to Chicago?

    Currently, September is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $180). Flying from West Virginia to Chicago in August is currently the most expensive (average of $279). 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
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Hammond
Porter
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Alternative routes for West Virginia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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Philadelphia to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
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Philadelphia to Midway flights
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Seattle to Midway flights

Top 2 airlines flying from West Virginia to Chicago

Discover the top 2 airlines that operate flights from West Virginia 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$275FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$260FlexibilityNo cancel feeOn-time71%

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