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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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$142
(Southwest)

One-way from

$64
(Southwest)

Popular in

November

Cheapest in

February

Average price

$618

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. 23% potential increase in price ($109 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($24 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 13, 2025.

This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amPIT - MDW
1 stop4h 55mSouthwest
Wed 12/102:10 pmMDW - PIT
2 stops5h 55mSouthwest
Deal found 11/10$142
This Priceline deal was found by Cheapflights users on 11/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:45 amIAD - ORD
1 stop7h 09mFrontier
Sun 12/76:11 amORD - IAD
1 stop9h 13mFrontier
Deal found 11/11$142
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/142:59 pmMDW - IAD
1 stop23h 06mFrontier
Deal found 11/11$142
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:05 pmPIT - ORD
1 stop8h 04mSpirit Airlines
Tue 12/99:14 pmORD - PIT
2 stops26h 27mSpirit Airlines
Deal found 11/10$143
This Southwest deal was found by Cheapflights users on 11/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:00 pmPIT - MDW
Nonstop1h 30mSouthwest
Thu 12/189:40 amMDW - PIT
Nonstop1h 25mSouthwest
Deal found 11/11$144
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Sat 12/62:10 pmPIT - ORD
Nonstop1h 44mUnited Airlines
Tue 12/910:36 amORD - PIT
Nonstop1h 30mUnited Airlines
Deal found 11/10$144
This Frontier deal was found by Cheapflights users on 11/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2010:15 pmIAD - ORD
1 stop11h 47mFrontier
Thu 1/16:00 amORD - IAD
1 stop11h 16mFrontier
Deal found 11/11$144
This Frontier deal was found by Cheapflights users on 11/12. 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.
Mon 12/226:05 amIAD - MDW
1 stop8h 16mFrontier
Thu 12/256:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 11/12$144
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Mon 12/86:58 pmIAD - ORD
2 stops17h 10mMultiple Airlines
Wed 12/108:00 amORD - IAD
1 stop5h 29mMultiple Airlines
Deal found 11/12$145
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:19 pmIAD - ORD
1 stop6h 05mFrontier
Sun 12/148:45 amORD - IAD
1 stop22h 46mFrontier
Deal found 11/11$146
This Trip.com deal was found by Cheapflights users on 11/11. 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 Trip.com 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 12/72:59 pmMDW - IAD
1 stop23h 06mFrontier
Deal found 11/11$146
This Booking.com deal was found by Cheapflights users on 11/13. 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 Booking.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 05mFrontier
Sun 12/78:45 amORD - IAD
1 stop22h 46mFrontier
Deal found 11/13$149

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 13, 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 - MDW

PITMDW

Pittsburgh

Thu 1/1

6:40 am-7:20 am

Nonstop1h 40m

Chicago Midway

Mon 1/5

4:15 pm-11:30 pm

1 stop6h 15m

$144

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 12/9

2:10 pm-2:54 pm

Nonstop1h 44m

Chicago O'Hare Intl

Thu 12/11

6:10 pm-8:50 pm

Nonstop1h 40m

$144

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 12/10

5:45 am-1:05 pm

2 stops8h 20m

Chicago Midway

Wed 12/10

2:10 pm-9:05 pm

2 stops5h 55m

$147

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 12/6

12:45 pm-4:20 pm

1 stop4h 35m

Chicago Midway

Wed 12/10

10:15 am-12:45 pm

Nonstop1h 30m

$154

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 1/15

5:30 am-12:15 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 1/17

1:45 pm-7:20 pm

1 stop4h 35m

$154

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 12/25

6:20 am-8:49 am

1 stop3h 29m

Chicago Midway

Wed 12/31

5:59 pm-11:36 pm

1 stop4h 37m

$157

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 11/24

5:35 pm-8:29 pm

1 stop3h 54m

Chicago O'Hare Intl

Thu 11/27

2:35 pm-6:56 pm

1 stop3h 21m

$157

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 12/6

12:15 pm-6:45 pm

1 stop7h 30m

Chicago Midway

Tue 12/9

6:40 am-2:55 pm

2 stops7h 15m

$169

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 12/11

3:44 pm-4:46 pm

Nonstop2h 02m

Chicago O'Hare Intl

Sat 12/13

3:20 pm-6:00 pm

Nonstop1h 40m

$171

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 12/13

2:10 pm-2:54 pm

Nonstop1h 44m

Chicago O'Hare Intl

Sat 1/10

9:05 pm-11:46 pm

Nonstop1h 41m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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 November is currently the most expensive (average of $280). 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 13, 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 13, 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).

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?

    Southwest, United Airlines, and Delta can get you from West Virginia to Chicago in just under 1h 40m. Your travel time can differ by up to 1h 49m. Airlines will cover a distance of 400 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 $64 and $72 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 November is currently the most expensive (average of $280). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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.
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Newark to St. Louis flights
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John F Kennedy Intl to St. Louis flights
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Orlando to Midway flights
Boston to Midway flights
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San Francisco 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 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$275FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$260FlexibilityNo cancel feeOn-time71%

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