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West Virginia

$49+ Cheap flights from Chicago (CHI) to West Virginia

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CRW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Chicago to West Virginia

Keep the following information in mind while searching for Chicago to West Virginia flight deals. Data was last updated September 15, 2025.

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

July

Cheapest in

March

Average price

$339

Good round-trip deal

$236 or less

Good one-way deal

$123 or less
From Chicago (CHI) to West Virginia
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One-way flight from Chicago (CHI) to West Virginia
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Highest demand for flights based on searches. 11% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to West Virginia.
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Price to beat on a one-way flight from Chicago (CHI) to West Virginia.
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Find flight deals from Chicago to West Virginia

Cheapest flights from Chicago to West Virginia
Explore the most affordable flight options available from Chicago to West Virginia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/166:40 pmMDW - PIT
Nonstop1h 20mSouthwest
Mon 10/205:50 pmPIT - MDW
1 stop7h 05mSouthwest
Deal found 9/14$107
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:35 pmMDW - PIT
Nonstop1h 20mSouthwest
Tue 10/146:10 amPIT - MDW
2 stops9h 15mSouthwest
Deal found 9/13$112
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/95:11 pmORD - PIT
Nonstop1h 30mAmerican Airlines
Sun 10/126:09 amPIT - ORD
Nonstop1h 48mAmerican Airlines
Deal found 9/13$115
This Southwest deal was found by Cheapflights users on 9/15. 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 10/153:10 pmORD - PIT
1 stop5h 20mSouthwest
Wed 10/225:50 amPIT - ORD
1 stop7h 00mSouthwest
Deal found 9/15$117
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:10 amMDW - PIT
1 stop5h 15mSouthwest
Thu 10/166:10 amPIT - MDW
2 stops9h 35mSouthwest
Deal found 9/13$122
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:10 pmORD - PIT
1 stop5h 20mSouthwest
Thu 10/166:10 amPIT - ORD
1 stop11h 15mSouthwest
Deal found 9/13$122
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:50 amORD - IAD
Nonstop2h 05mUnited Airlines
Sun 10/56:30 amIAD - ORD
Nonstop2h 11mUnited Airlines
Deal found 9/12$133
This CheapOair deal was found by Cheapflights users on 9/14. 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 10/249:45 amMDW - IAD
1 stop9h 23mFrontier
Mon 10/275:00 pmIAD - MDW
1 stop7h 46mFrontier
Deal found 9/14$143
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amORD - IAD
1 stop8h 26mFrontier
Mon 10/204:45 pmIAD - ORD
1 stop7h 54mFrontier
Deal found 9/14$143
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1811:31 amMDW - IAD
1 stop8h 22mFrontier
Mon 10/204:45 pmIAD - MDW
1 stop8h 01mFrontier
Deal found 9/14$144
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2411:45 amORD - IAD
1 stop7h 10mFrontier
Thu 9/251:55 pmIAD - ORD
1 stop11h 15mFrontier
Deal found 9/13$144
This Frontier deal was found by Cheapflights users on 9/14. 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 9/296:10 amORD - PIT
1 stop6h 22mFrontier
Fri 10/39:34 amPIT - ORD
1 stop11h 10mFrontier
Deal found 9/14$144

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to West Virginia 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to West Virginia that are best for you.

Fly from

Chicago

Fly to

West Virginia

Route

Depart

Return

Price

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Mon 10/27

1:30 pm-3:50 pm

Nonstop1h 20m

Pittsburgh

Thu 10/30

6:00 pm-10:20 pm

1 stop5h 20m

$107

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Wed 10/15

10:05 am-12:25 pm

Nonstop1h 20m

Pittsburgh

Thu 10/16

6:10 am-2:45 pm

2 stops9h 35m

$112

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 10/11

5:35 pm-7:55 pm

Nonstop1h 20m

Pittsburgh

Tue 10/14

6:10 am-2:25 pm

2 stops9h 15m

$112

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Mon 10/27

2:50 pm-10:25 pm

1 stop6h 35m

Pittsburgh

Thu 10/30

12:50 pm-4:25 pm

1 stop4h 35m

$117

ChicagoPittsburgh

ORD - PIT

ORDPIT

Chicago O'Hare Intl

Wed 10/15

3:10 pm-9:30 pm

1 stop5h 20m

Pittsburgh

Thu 10/16

6:10 am-4:25 pm

1 stop11h 15m

$122

ChicagoPittsburgh

MDW - PIT

MDWPIT

Chicago Midway

Sat 12/13

9:50 am-5:15 pm

2 stops6h 25m

Pittsburgh

Mon 12/15

7:55 am-5:00 pm

2 stops10h 05m

$127

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/4

11:21 am-6:29 pm

1 stop6h 08m

Washington, D.C. Dulles Intl

Mon 10/6

1:55 pm-11:41 pm

1 stop10h 46m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 10/15

8:05 am-7:46 pm

1 stop10h 41m

Washington, D.C. Dulles Intl

Fri 10/17

9:28 pm-10:21 am

1 stop13h 53m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/25

6:15 am-3:17 pm

1 stop8h 02m

Washington, D.C. Dulles Intl

Wed 10/29

8:47 am-12:41 pm

1 stop4h 54m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/17

5:28 pm-8:53 pm

1 stop26h 25m

Washington, D.C. Dulles Intl

Mon 10/20

4:45 pm-11:46 pm

1 stop8h 01m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to West Virginia (average of $304). Flying from Chicago to West Virginia in December is currently the most expensive (average of $448). 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 CHI to WV?

Find hourly flight availability from Chicago to West Virginia. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Chicago to West Virginia, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to West Virginia

Explore weekly flight availability from Chicago to West Virginia. 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 September 15, 2025.

The most flights from CHI to USWV 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).

Reviews of airlines servicing West Virginia

Get insights into the airlines that provide service to West Virginia. 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 West Virginia. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Chicago to West Virginia, such as United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Chicago to West Virginia. 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 Chicago to West Virginia?

    Southwest, Frontier, and United Airlines can get you from Chicago to West Virginia in just under 1h 20m. Your travel time can differ by up to 4h 48m. 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 Chicago to West Virginia one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $49. Users have also found prices from $49 and $78 on United Airlines and Frontier, respectively.

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

    While some choose either Chicago Midway - Washington, D.C. Dulles Intl or Chicago O'Hare Intl - Pittsburgh, Chicago O'Hare Intl - Washington, D.C. Dulles Intl is the most popular route from Chicago to West Virginia.

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

    Before booking your flight to West Virginia from Chicago, check out the most reliable airlines to get you to your destination on time: SkyWest Airlines (65%), United Airlines (65%), ANA( 63%).

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

    On average you can expect to pay $311 for a flight from Chicago to West Virginia. The cheapest flight overall is $209 while the most popular route, (Chicago O'Hare Intl - Washington, D.C. Dulles Intl) is currently priced at $133.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to West Virginia (average of $304). Flying from Chicago to West Virginia in December is currently the most expensive (average of $448). 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

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Alternative routes for Chicago to West Virginia

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to West Virginia

Discover the top 2 airlines that operate flights from Chicago to West Virginia. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$190Average$281FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$313FlexibilityNo cancel feeOn-time71%

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