$84+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Jul 7 — Jul 141
1 adult, Economy
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Find cheap flights from West Virginia to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 July 2, 2025.
Round-trip from | $150 (KAYAK) |
|---|---|
One-way from | $85 (Priceline) |
Popular in | July |
Cheapest in | February |
Average price | $541 |
Good round-trip deal | $162 or less |
Good one-way deal | $254 or less |
Find flight deals from West Virginia to Chicago
Cheapest flights from West Virginia to ChicagoExplore 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 July 2, 2025.
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 July 2, 2025.
This KAYAK deal was found by Cheapflights users on 7/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/291:45 pmPIT - MDW
Nonstop1h 25mSouthwest
Wed 7/309:25 pmMDW - PIT
Nonstop1h 25mSouthwest
Deal found 7/2![Southwest logo]()
$150
This Frontier deal was found by Cheapflights users on 6/30. 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.
Wed 7/236:10 amIAD - MDW
1 stop5h 30mFrontier
Tue 7/2911:39 amMDW - IAD
1 stop11h 33mFrontier
Deal found 6/30![Frontier logo]()
$150
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/59:36 amPIT - ORD
1 stop11h 04mFrontier
Sun 9/76:10 amORD - PIT
1 stop7h 26mFrontier
Deal found 7/1![Frontier logo]()
$151
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:10 amIAD - ORD
1 stop5h 18mFrontier
Sun 9/75:10 amORD - IAD
1 stop6h 36mFrontier
Deal found 6/30![Frontier logo]()
$151
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Mon 8/44:09 pmPIT - ORD
Nonstop1h 56mUnited Airlines
Sat 8/169:10 pmORD - PIT
Nonstop1h 38mUnited Airlines
Deal found 6/30![United Airlines logo]()
$154
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/253:49 pmPIT - MDW
1 stop9h 02mFrontier
Mon 7/288:35 amMDW - PIT
1 stop10h 03mFrontier
Deal found 7/2![Frontier logo]()
$163
This Southwest deal was found by Cheapflights users on 6/30. 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 8/276:00 amPIT - ORD
1 stop6h 50mSouthwest
Sat 8/302:55 pmORD - PIT
1 stop4h 00mSouthwest
Deal found 6/30![Southwest logo]()
$165
This United Airlines deal was found by Cheapflights users on 6/30. 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 8/2310:10 pmIAD - ORD
Nonstop2h 05mUnited Airlines
Thu 8/2812:50 pmORD - IAD
Nonstop2h 02mUnited Airlines
Deal found 6/30![United Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/158:38 pmPIT - ORD
Nonstop1h 46mAmerican Airlines
Sun 8/248:54 pmORD - PIT
Nonstop1h 50mAmerican Airlines
Deal found 6/30![American Airlines logo]()
$171
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:00 pmLWB - ORD
Nonstop1h 45mContour
Mon 10/132:10 pmORD - LWB
Nonstop1h 45mContour
Deal found 7/1![Contour logo]()
$171
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/55:45 amPIT - MDW
1 stop7h 03mDelta
Mon 8/116:17 pmMDW - PIT
1 stop4h 42mDelta
Deal found 7/2![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/46:31 pmPIT - ORD
1 stop6h 38mDelta
Tue 8/125:45 amORD - PIT
1 stop5h 53mDelta
Deal found 6/30![Delta logo]()
$177
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 July 2, 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 7/29
1:45 pm-2:10 pm
Nonstop1h 25m
Chicago Midway
Wed 7/30
9:25 pm-11:50 pm
Nonstop1h 25m
$150
Washington, D.C.Chicago
IAD - MDW
IADMDW
Washington, D.C. Dulles Intl
Wed 7/23
6:10 am-10:40 am
1 stop5h 30m
Chicago Midway
Tue 7/29
11:39 am-12:12 am
1 stop11h 33m
$150
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 9/5
9:36 am-7:40 pm
1 stop11h 04m
Chicago O'Hare Intl
Sun 9/7
6:10 am-2:36 pm
1 stop7h 26m
$151
Washington, D.C.Chicago
IAD - ORD
IADORD
Washington, D.C. Dulles Intl
Thu 9/4
6:10 am-10:28 am
1 stop5h 18m
Chicago O'Hare Intl
Sun 9/7
5:10 am-12:46 pm
1 stop6h 36m
$151
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Mon 8/4
4:09 pm-5:05 pm
Nonstop1h 56m
Chicago O'Hare Intl
Sat 8/16
9:10 pm-11:48 pm
Nonstop1h 38m
$154
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 7/25
3:49 pm-11:51 pm
1 stop9h 02m
Chicago Midway
Mon 7/28
8:35 am-7:38 pm
1 stop10h 03m
$163
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Wed 8/27
6:00 am-11:50 am
1 stop6h 50m
Chicago O'Hare Intl
Sat 8/30
2:55 pm-7:55 pm
1 stop4h 00m
$165
Washington, D.C.Chicago
IAD - ORD
IADORD
Washington, D.C. Dulles Intl
Sat 8/23
10:10 pm-11:15 pm
Nonstop2h 05m
Chicago O'Hare Intl
Thu 8/28
12:50 pm-3:52 pm
Nonstop2h 02m
$169
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 8/15
8:38 pm-9:24 pm
Nonstop1h 46m
Chicago O'Hare Intl
Sun 8/24
8:54 pm-11:44 pm
Nonstop1h 50m
$171
LewisburgChicago
LWB - ORD
LWBORD
Lewisburg Greenbrier Valley
Fri 10/10
6:00 pm-6:45 pm
Nonstop1h 45m
Chicago O'Hare Intl
Mon 10/13
2:10 pm-4:55 pm
Nonstop1h 45m
$171
Showing 1-10 of 60 results
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 July 2, 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 July 2, 2025.
The most flights from USWV to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from West Virginia to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 2, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from West Virginia to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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.
Traveling to a place near West Virginia?
Book flights to West Virginia if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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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.
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 July 2, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$178 | Average$280 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$260 | FlexibilityNo cancel fee | On-time69% |