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$70+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheap 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 April 23, 2026.

This Southwest deal was found by Cheapflights users on 4/23. 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 5/197:10 pm
PIT
-
MDW
Nonstop1h 30m
Southwest
Thu 5/217:40 am
MDW
-
PIT
Nonstop1h 20m
Southwest
Deal found 4/23$177
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/278:15 pm
PIT
-
ORD
1 stop27h 58m
Multiple Airlines
Wed 6/38:05 am
ORD
-
PIT
1 stop8h 35m
Multiple Airlines
Deal found 4/21$180
This Southwest deal was found by Cheapflights users on 4/23. 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 5/266:55 pm
PIT
-
MDW
1 stop4h 20m
Southwest
Thu 5/287:40 am
MDW
-
PIT
Nonstop1h 20m
Southwest
Deal found 4/23$187
This Southwest deal was found by Cheapflights users on 4/20. 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 5/188:00 pm
PIT
-
MDW
Nonstop1h 30m
Southwest
Wed 5/206:20 pm
MDW
-
PIT
Nonstop1h 25m
Southwest
Deal found 4/20$192
This Southwest deal was found by Cheapflights users on 4/20. 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 6/26:25 am
PIT
-
MDW
2 stops10h 20m
Southwest
Wed 6/310:05 am
MDW
-
PIT
2 stops7h 10m
Southwest
Deal found 4/20$193
This United Airlines deal was found by Cheapflights users on 4/19. 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 5/132:15 pm
CKB
-
ORD
Nonstop1h 56m
United Airlines
Sun 5/174:25 pm
ORD
-
CKB
Nonstop1h 44m
United Airlines
Deal found 4/19$194
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/184:58 pm
PIT
-
ORD
2 stops15h 57m
Multiple Airlines
Thu 5/288:05 am
ORD
-
PIT
1 stop13h 02m
Multiple Airlines
Deal found 4/19$200
This Southwest deal was found by Cheapflights users on 4/20. 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 5/285:55 am
PIT
-
ORD
1 stop7h 55m
Southwest
Mon 6/12:40 pm
ORD
-
PIT
1 stop6h 35m
Southwest
Deal found 4/20$202
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/244:58 pm
PIT
-
ORD
1 stop7h 15m
Multiple Airlines
Tue 5/265:11 pm
ORD
-
PIT
1 stop25h 09m
Multiple Airlines
Deal found 4/18$212
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Fri 5/154:05 pm
LWB
-
ORD
Nonstop2h 13m
American Airlines
Sat 5/162:57 pm
ORD
-
LWB
Nonstop1h 53m
American Airlines
Deal found 4/18$214
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/278:15 pm
PIT
-
ORD
2 stops24h 26m
Multiple Airlines
Sat 5/305:11 pm
ORD
-
PIT
1 stop17h 07m
Multiple Airlines
Deal found 4/22$216
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Tue 5/1911:07 am
IAD
-
MDW
1 stop11h 55m
Multiple Airlines
Thu 5/219:14 am
MDW
-
IAD
1 stop7h 14m
Multiple Airlines
Deal found 4/22$219

Find 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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$180
(Kiwi.com)

One-way from

$70
(Frontier)

Popular in

July

Cheapest in

February

Average price

$274

Good round-trip deal

$273 or less

Good one-way deal

$320 or less
Provider with most accurate pricing for Charleston Yeager-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charleston Yeager-Chicago (CHI) flights.
Search Deals
From West Virginia to Chicago (CHI)
Search Deals
One-way flight from West Virginia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from West Virginia to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from West Virginia to Chicago (CHI).
Search Deals

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 April 23, 2026.
Use the filters below to find and compare flights from West Virginia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClarksburgChicago

CKB - ORD

CKBORD

Clarksburg Benedum

Mon 5/25

2:25 pm-3:19 pm

Nonstop1h 54m

Chicago O'Hare Intl

Tue 6/2

4:35 pm-7:23 pm

Nonstop1h 48m

$194

ClarksburgChicago

CKB - ORD

CKBORD

Clarksburg Benedum

Tue 5/19

2:15 pm-3:11 pm

Nonstop1h 56m

Chicago O'Hare Intl

Tue 6/2

4:35 pm-7:23 pm

Nonstop1h 48m

$194
Quickest round-trip

ClarksburgChicago

CKB - ORD

CKBORD

Clarksburg Benedum

Wed 5/13

2:15 pm-3:11 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 5/17

4:25 pm-7:09 pm

Nonstop1h 44m

$194

ClarksburgChicago

CKB - ORD

CKBORD

Clarksburg Benedum

Thu 5/21

2:25 pm-3:19 pm

Nonstop1h 54m

Chicago O'Hare Intl

Thu 5/28

4:35 pm-7:23 pm

Nonstop1h 48m

$194

LewisburgChicago

LWB - ORD

LWBORD

Lewisburg Greenbrier Valley

Fri 5/22

4:26 pm-5:33 pm

Nonstop2h 07m

Chicago O'Hare Intl

Mon 5/25

3:08 pm-6:03 pm

Nonstop1h 55m

$214

LewisburgChicago

LWB - ORD

LWBORD

Lewisburg Greenbrier Valley

Tue 5/19

4:41 pm-5:56 pm

Nonstop2h 15m

Chicago O'Hare Intl

Tue 5/26

3:08 pm-6:03 pm

Nonstop1h 55m

$214

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 6/2

10:31 am-11:53 am

Nonstop2h 22m

Chicago O'Hare Intl

Fri 6/5

1:18 pm-4:26 pm

Nonstop2h 08m

$233

ClarksburgChicago

CKB - ORD

CKBORD

Clarksburg Benedum

Fri 7/3

2:25 pm-3:19 pm

Nonstop1h 54m

Chicago O'Hare Intl

Tue 7/7

4:35 pm-7:23 pm

Nonstop1h 48m

$234

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 6/30

5:52 pm-6:56 pm

Nonstop2h 04m

Chicago O'Hare Intl

Tue 7/7

8:00 pm-10:53 pm

Nonstop1h 53m

$239

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/30

6:08 am-9:59 am

1 stop4h 51m

Chicago Midway

Mon 6/1

9:22 am-4:31 pm

1 stop6h 09m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 resultsSorted by cheapest first
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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, February is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $145). Flying from West Virginia to Chicago in March is currently the most expensive (average of $268). 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 April 23, 2026.

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 17% versus a flight in the morning.

What is the cheapest day to fly from West Virginia to Chicago?

Use this chart to determine the cheapest time to fly round-trip from West Virginia to Chicago. Price data was last updated on April 18, 2026.

Travelers seeking maximum savings on their West Virginia to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 April 23, 2026.

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 (3 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?

    United Airlines, American Airlines, and Delta can get you from West Virginia to Chicago in just under 1h 54m. Your travel time can differ by up to 2h 57m. Airlines will cover a distance of 442 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 (61%), SkyWest Airlines (59%) or United Airlines (59%) 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 $228. On average you can expect to pay $447. The most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), can usually be booked for $171.

  • 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, February is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $145). Flying from West Virginia to Chicago in March is currently the most expensive (average of $268). 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
Benton Harbor
Lansing
Merrillville
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.
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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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$145Average$309FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$218Average$218FlexibilityNo cancel feeOn-time71%

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