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$43+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Wed 1/73:01 pmMDW - IAD
1 stop21h 00mFrontier
Deal found 12/14$191
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Fri 1/93:01 pmMDW - IAD
1 stop21h 15mFrontier
Deal found 12/14$203
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amCRW - ORD
Nonstop2h 05mUnited Airlines
Sun 1/410:35 amORD - CRW
Nonstop1h 47mUnited Airlines
Deal found 12/16$209
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/169:00 amIAD - ORD
1 stop10h 46mFrontier
Sat 1/108:27 pmORD - IAD
1 stop10h 13mFrontier
Deal found 12/13$213
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Mon 1/124:31 pmMDW - IAD
2 stops18h 12mFrontier
Deal found 12/14$213
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Sun 1/114:21 pmMDW - IAD
1 stop14h 19mFrontier
Deal found 12/14$214
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Thu 1/812:41 pmMDW - IAD
2 stops18h 14mFrontier
Deal found 12/14$220
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Tue 12/308:15 pmIAD - MDW
2 stops19h 22mFrontier
Wed 1/73:01 pmMDW - IAD
1 stop21h 00mFrontier
Deal found 12/14$221
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:31 pmIAD - ORD
Nonstop2h 21mUnited Airlines
Wed 12/312:30 pmORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 12/14$223
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 amCRW - ORD
Nonstop2h 05mUnited Airlines
Sat 1/310:35 amORD - CRW
Nonstop1h 47mUnited Airlines
Deal found 12/16$224
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Tue 12/308:15 pmIAD - MDW
2 stops19h 22mFrontier
Fri 1/93:01 pmMDW - IAD
1 stop21h 15mFrontier
Deal found 12/14$233
This Frontier deal was found by Cheapflights users on 12/14. 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 12/299:58 pmIAD - ORD
1 stop12h 04mFrontier
Mon 1/56:00 amORD - IAD
1 stop11h 16mFrontier
Deal found 12/14$234

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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$146
(Kiwi.com)

One-way from

$43
(Priceline)

Popular in

July

Cheapest in

February

Average price

$299

Good round-trip deal

$329 or less

Good one-way deal

$273 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.
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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. 10% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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).
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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 December 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

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/5

11:22 am-10:29 pm

1 stop12h 07m

Chicago Midway

Wed 3/11

11:19 am-7:24 am

1 stop19h 05m

$162

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Thu 2/5

7:00 am-7:51 am

Nonstop1h 51m

Chicago O'Hare Intl

Mon 2/9

6:04 pm-8:41 pm

Nonstop1h 37m

$171

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Tue 1/20

2:06 pm-2:55 pm

Nonstop1h 49m

Chicago O'Hare Intl

Mon 1/26

6:04 pm-8:41 pm

Nonstop1h 37m

$171

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 1/17

9:00 am-5:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Wed 1/21

7:45 am-2:41 pm

1 stop5h 56m

$175

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 1/29

5:37 pm-6:39 pm

Nonstop2h 02m

Chicago O'Hare Intl

Sat 1/31

6:09 pm-8:56 pm

Nonstop1h 47m

$179

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 1/22

5:50 am-6:40 am

Nonstop1h 50m

Chicago Midway

Mon 1/26

2:35 pm-8:45 pm

1 stop5h 10m

$181

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Tue 1/20

10:00 am-6:50 pm

2 stops9h 50m

Chicago Midway

Thu 1/22

1:25 pm-8:45 pm

2 stops6h 20m

$182

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Fri 1/16

1:00 pm-2:39 pm

1 stop26h 39m

Chicago O'Hare Intl

Mon 1/19

8:43 pm-9:40 am

1 stop11h 57m

$186

PittsburghChicago

PIT - MDW

PITMDW

Pittsburgh

Thu 2/5

5:40 am-6:30 am

Nonstop1h 50m

Chicago Midway

Mon 2/9

3:05 pm-10:35 pm

2 stops6h 30m

$186

PittsburghChicago

PIT - ORD

PITORD

Pittsburgh

Sat 1/17

9:00 am-5:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Sun 1/18

7:45 am-2:41 pm

1 stop5h 56m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, 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 $279). 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 December 16, 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 49% versus a flight at noon.

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?

    Frontier, United Airlines, and JetBlue can get you from West Virginia to Chicago in just under 1h 51m. Your travel time can differ by up to 10h 16m. 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 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 (71%), Emirates (55%) or Air New Zealand (47%) 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 $205. On average you can expect to pay $439. The most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), can usually be booked for $212.

  • 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 $279). 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
Merrillville
Hammond
Porter
Benton Harbor

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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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$274FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$198Average$260FlexibilityNo cancel feeOn-time71%

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