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$49+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

December

Cheapest in

February

Average price

$369

Good round-trip deal

$290 or less

Good one-way deal

$104 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. 15% potential increase in price ($61 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 September 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 September 16, 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.
Tue 10/146:20 amPIT - MDW
Nonstop1h 30mSouthwest
Tue 10/211:25 pmMDW - PIT
Nonstop1h 20mSouthwest
Deal found 9/14$97
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/142:07 pmPIT - ORD
Nonstop1h 44mUnited Airlines
Thu 10/1610:35 amORD - PIT
Nonstop1h 30mUnited Airlines
Deal found 9/15$97
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:17 amPIT - ORD
Nonstop1h 42mAmerican Airlines
Mon 10/138:50 pmORD - PIT
Nonstop1h 29mAmerican Airlines
Deal found 9/15$98
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.
Tue 10/144:00 pmPIT - MDW
Nonstop1h 25mSouthwest
Wed 10/157:55 amMDW - PIT
1 stop3h 30mSouthwest
Deal found 9/15$107
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 10/156:45 pmPIT - MDW
Nonstop1h 30mSouthwest
Sat 10/186:30 amMDW - PIT
1 stop7h 40mSouthwest
Deal found 9/15$113
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 10/85:50 amPIT - ORD
1 stop7h 00mSouthwest
Tue 10/213:10 pmORD - PIT
1 stop5h 20mSouthwest
Deal found 9/15$117
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.
Mon 10/206:00 amPIT - ORD
1 stop7h 45mSouthwest
Wed 10/223:10 pmORD - PIT
1 stop5h 20mSouthwest
Deal found 9/15$122
This Southwest deal was found by Cheapflights users on 9/16. 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.
Wed 10/156:10 amPIT - ORD
1 stop7h 35mSouthwest
Sat 10/181:30 pmORD - PIT
1 stop7h 20mSouthwest
Deal found 9/16$128
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/184:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/209:44 amMDW - IAD
1 stop4h 55mFrontier
Deal found 9/15$138
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:00 amIAD - MDW
1 stop5h 38mFrontier
Tue 10/218:05 amMDW - IAD
1 stop10h 41mFrontier
Deal found 9/14$140
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 10/254:22 pmIAD - ORD
1 stop8h 07mFrontier
Mon 10/2712:23 pmORD - IAD
1 stop9h 59mFrontier
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 10/254:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/2712:03 pmMDW - IAD
1 stop10h 19mFrontier
Deal found 9/14$143

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 September 16, 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

Tue 10/14

6:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Tue 10/21

1:25 pm-3:45 pm

Nonstop1h 20m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/14

7:00 pm-7:50 pm

Nonstop1h 50m

Chicago O'Hare Intl

Tue 10/21

10:35 am-1:05 pm

Nonstop1h 30m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 11/8

6:45 am-7:25 am

Nonstop1h 40m

Chicago Midway

Thu 11/13

9:40 am-12:05 pm

Nonstop1h 25m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 10/14

2:07 pm-2:51 pm

Nonstop1h 44m

Chicago O'Hare Intl

Thu 10/16

10:35 am-1:05 pm

Nonstop1h 30m

$97

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 11/13

11:00 am-11:44 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 11/15

7:25 am-9:54 am

Nonstop1h 29m

$97

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 10/30

8:10 pm-8:40 pm

Nonstop1h 30m

Chicago Midway

Sat 11/1

9:40 am-4:00 pm

1 stop5h 20m

$107

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Sat 10/25

4:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Tue 10/28

6:10 am-12:25 pm

1 stop5h 15m

$107

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 10/14

6:10 am-2:25 pm

2 stops9h 15m

Chicago Midway

Thu 10/16

6:40 pm-9:00 pm

Nonstop1h 20m

$112

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Mon 10/20

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Wed 10/22

3:10 pm-9:30 pm

1 stop5h 20m

$122

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 9/29

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Mon 10/6

8:19 am-6:24 pm

1 stop9h 05m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 September 16, 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.

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 September 16, 2025.

The most flights from USWV to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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?

    Southwest, United Airlines, and Frontier can get you from West Virginia to Chicago in just under 1h 30m. Your travel time can differ by up to 8h 55m. 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 $49. Users have also found prices from $49 and $78 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 (79%), SkyWest Airlines (64%) or United Airlines (64%) 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 $219. On average you can expect to pay $676. The most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), can usually be booked for $117.

  • 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
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$277FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$280FlexibilityNo cancel feeOn-time71%

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