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$46+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$91
(American Airlines)

One-way from

$46
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$339

Good round-trip deal

$182 or less

Good one-way deal

$129 or less
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 ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 10/86:09 amPIT - ORD
Nonstop1h 48mAmerican Airlines
Wed 10/812:11 pmORD - PIT
Nonstop1h 31mAmerican Airlines
Deal found 8/18$91
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/166:10 amPIT - MDW
2 stops7h 30mSouthwest
Tue 9/233:25 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 8/17$92
This Southwest deal was found by Cheapflights users on 8/18. 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 10/46:20 amPIT - MDW
Nonstop1h 30mSouthwest
Tue 10/71:25 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 8/18$97
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/166:00 amPIT - ORD
1 stop6h 50mSouthwest
Tue 9/233:10 pmORD - PIT
1 stop5h 10mSouthwest
Deal found 8/17$97
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/105:23 pmPIT - ORD
Nonstop1h 47mAmerican Airlines
Mon 9/1512:12 pmORD - PIT
Nonstop1h 32mAmerican Airlines
Deal found 8/17$104
This Southwest deal was found by Cheapflights users on 8/16. 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.
Tue 9/166:40 pmPIT - MDW
Nonstop1h 25mSouthwest
Thu 9/186:30 amMDW - PIT
1 stop3h 30mSouthwest
Deal found 8/16$107
This Southwest deal was found by Cheapflights users on 8/17. 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 9/116:25 amPIT - MDW
Nonstop1h 25mSouthwest
Mon 9/159:15 pmMDW - PIT
Nonstop1h 25mSouthwest
Deal found 8/17$117
This American Airlines deal was found by Cheapflights users on 8/17. 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 10/212:35 pmPIT - ORD
Nonstop1h 50mAmerican Airlines
Sat 10/49:28 amORD - PIT
Nonstop1h 48mAmerican Airlines
Deal found 8/17$117
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/115:23 pmPIT - ORD
Nonstop1h 47mAmerican Airlines
Mon 9/156:45 pmORD - PIT
Nonstop1h 46mAmerican Airlines
Deal found 8/16$118
This Southwest deal was found by Cheapflights users on 8/18. 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 10/42:05 pmPIT - ORD
1 stop8h 25mSouthwest
Tue 10/71:50 pmORD - PIT
1 stop7h 30mSouthwest
Deal found 8/18$122
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 10/18:35 amPIT - ORD
Nonstop1h 50mUnited Airlines
Wed 10/810:35 amORD - PIT
Nonstop1h 30mUnited Airlines
Deal found 8/18$137
This Southwest deal was found by Cheapflights users on 8/17. 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 10/26:10 amPIT - ORD
1 stop11h 15mSouthwest
Sat 10/412:40 pmORD - PIT
1 stop6h 05mSouthwest
Deal found 8/17$142

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 August 18, 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

Wed 10/15

7:17 am-7:59 am

Nonstop1h 42m

Chicago O'Hare Intl

Wed 10/15

12:11 pm-2:42 pm

Nonstop1h 31m

$91

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 9/16

6:10 am-12:40 pm

2 stops7h 30m

Chicago Midway

Tue 9/23

3:25 pm-5:45 pm

Nonstop1h 20m

$92

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 10/4

11:04 am-11:47 am

Nonstop1h 43m

Chicago O'Hare Intl

Tue 10/7

2:15 pm-4:52 pm

Nonstop1h 37m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/11

4:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Wed 10/15

10:05 am-12:25 pm

Nonstop1h 20m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 9/16

8:46 am-9:36 am

Nonstop1h 50m

Chicago O'Hare Intl

Thu 9/18

10:35 am-1:05 pm

Nonstop1h 30m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 11/4

6:45 pm-7:15 pm

Nonstop1h 30m

Chicago Midway

Thu 11/6

9:40 am-12:05 pm

Nonstop1h 25m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Wed 9/17

6:00 pm-6:43 pm

Nonstop1h 43m

Chicago O'Hare Intl

Thu 9/18

7:24 am-10:01 am

Nonstop1h 37m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 9/16

6:40 pm-7:05 pm

Nonstop1h 25m

Chicago Midway

Thu 9/18

9:15 pm-11:40 pm

Nonstop1h 25m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Wed 9/17

2:55 pm-3:20 pm

Nonstop1h 25m

Chicago Midway

Thu 9/18

9:15 pm-11:40 pm

Nonstop1h 25m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/4

4:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Tue 10/7

4:55 pm-7:15 pm

Nonstop1h 20m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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, August is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $245). Flying from 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 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 August 18, 2025.

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

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?

    American Airlines, Southwest, and United Airlines can get you from West Virginia to Chicago in just under 1h 42m. Your travel time can differ by up to 5h 48m. 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 American Airlines. According to our data, you can fly for as low as $46. Users have also found prices from $49 and $79 on Southwest 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 (78%), SkyWest Airlines (71%) or United Airlines (71%) 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 $209. On average you can expect to pay $474. The most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), can usually be booked for $151.

  • 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, August is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $245). Flying from 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
Chesterton

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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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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$259FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$280FlexibilityNo cancel feeOn-time71%

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