$59+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Jun 14 — Jun 211
Round-trip
1 adult, Economy
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Find cheap flights from West Virginia to Chicago with Cheapflights
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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
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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 May 15, 2026.
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 May 15, 2026.
This Southwest deal was found by Cheapflights users on 5/11. 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 6/18:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sat 6/66:30 am
MDW
- PIT
1 stop5h 40m
Southwest
Deal found 5/11![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 5/12. 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 6/24:10 pm
PIT
- ORD
Nonstop1h 51m
United Airlines
Wed 6/310:29 am
ORD
- PIT
Nonstop1h 42m
United Airlines
Deal found 5/12![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:30 am
PIT
- MDW
1 stop3h 44m
Delta
Tue 7/76:58 pm
MDW
- PIT
1 stop4h 06m
Delta
Deal found 5/14![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:25 pm
PIT
- MDW
1 stop6h 00m
Southwest
Tue 6/96:10 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$192
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:16 pm
PIT
- ORD
1 stop4h 30m
American Airlines
Tue 9/89:00 am
ORD
- PIT
Nonstop1h 49m
American Airlines
Deal found 5/13![American Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 5/10. 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 8/132:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 8/175:30 am
MDW
- PIT
1 stop10h 35m
Southwest
Deal found 5/10![Southwest logo]()
$193
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/112:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Wed 6/174:35 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 5/12![United Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:31 am
PIT
- MDW
1 stop3h 11m
Delta
Mon 6/86:58 pm
MDW
- PIT
1 stop4h 09m
Delta
Deal found 5/13![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:00 pm
PIT
- ORD
1 stop6h 05m
Delta
Mon 6/87:17 pm
ORD
- PIT
1 stop3h 50m
Delta
Deal found 5/13![Delta logo]()
$197
This American Airlines deal was found by Cheapflights users on 5/15. 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.
Tue 8/46:23 am
PIT
- ORD
Nonstop1h 58m
American Airlines
Sat 8/86:55 am
ORD
- PIT
1 stop5h 18m
American Airlines
Deal found 5/15![American Airlines logo]()
$202
This Delta deal was found by Cheapflights users on 5/11. 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 6/15:40 am
PIT
- MDW
1 stop5h 20m
Delta
Sat 6/66:36 pm
MDW
- PIT
1 stop2h 46m
Delta
Deal found 5/11![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/15. 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 8/2510:45 am
PIT
- ORD
Nonstop1h 44m
United Airlines
Tue 9/12:30 pm
ORD
- PIT
Nonstop1h 44m
United Airlines
Deal found 5/15![United Airlines logo]()
$207
Best flights from West Virginia to ChicagoDiscover carefully curated flight deals from West Virginia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 15, 2026.
Discover carefully curated flight deals from West Virginia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 15, 2026.
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Thu 6/112:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Wed 6/174:35 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 5/14![United Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 5/10. 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.
Sat 6/136:20 pm
PIT
- MDW
1 stop4h 57m
Delta
Mon 6/156:58 pm
MDW
- PIT
1 stop4h 09m
Delta
Deal found 5/10![Delta logo]()
$197
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/54:26 pm
LWB
- ORD
Nonstop2h 09m
American Airlines
Mon 6/83:08 pm
ORD
- LWB
Nonstop1h 54m
American Airlines
Deal found 5/12![American Airlines logo]()
$214
This KAYAK deal was found by Cheapflights users on 5/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:50 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Wed 6/107:50 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 5/14![Southwest logo]()
$217
This Frontier deal was found by Cheapflights users on 5/10. 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.
Thu 6/411:07 am
IAD
- MDW
1 stop11h 55m
Frontier
Thu 6/116:00 am
MDW
- IAD
1 stop9h 52m
Frontier
Deal found 5/10![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Thu 6/412:41 pm
PIT
- RFD
1 stop20h 04m
Allegiant Air
Sun 6/79:19 am
RFD
- PIT
1 stop12h 45m
Allegiant Air
Deal found 5/12![Allegiant Air logo]()
$307
This United Airlines deal was found by Cheapflights users on 5/10. 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.
Fri 6/192:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Mon 6/224:35 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 5/10![United Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:31 am
PIT
- ORD
1 stop3h 30m
Delta
Mon 6/87:17 pm
ORD
- PIT
1 stop3h 50m
Delta
Deal found 5/14![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Thu 6/412:41 pm
PIT
- RFD
1 stop20h 04m
Multiple Airlines
Mon 6/87:53 pm
RFD
- PIT
2 stops15h 15m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 5/10. 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.
Thu 7/92:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Tue 7/144:41 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 5/10![United Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sun 6/74:26 pm
LWB
- ORD
Nonstop2h 09m
American Airlines
Sat 6/133:06 pm
ORD
- LWB
Nonstop1h 54m
American Airlines
Deal found 5/10![American Airlines logo]()
$214
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/34:26 pm
LWB
- ORD
Nonstop2h 07m
American Airlines
Sat 6/63:06 pm
ORD
- LWB
Nonstop1h 54m
American Airlines
Deal found 5/11![American Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 5/11. 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 6/310:10 am
MDW
- PIT
2 stops6h 45m
Southwest
Deal found 5/11![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:20 am
PIT
- ORD
1 stop6h 21m
Delta
Sat 9/127:10 am
ORD
- PIT
1 stop3h 01m
Delta
Deal found 5/13![Delta logo]()
$258
This United Airlines deal was found by Cheapflights users on 5/12. 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 6/1011:00 am
CRW
- ORD
Nonstop1h 58m
United Airlines
Wed 6/175:50 pm
ORD
- CRW
Nonstop1h 52m
United Airlines
Deal found 5/12![United Airlines logo]()
$239
This KAYAK deal was found by Cheapflights users on 5/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:31 pm
PIT
- ORD
1 stop7h 02m
American Airlines
Wed 6/104:50 pm
ORD
- PIT
Nonstop1h 38m
American Airlines
Deal found 5/14![American Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 5/14. 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.
Thu 8/138:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Sun 8/163:20 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 5/14![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 5/11. 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.
Sat 6/136:14 am
IAD
- MDW
1 stop7h 55m
Delta
Tue 6/166:00 am
MDW
- IAD
1 stop4h 39m
Delta
Deal found 5/11![Delta logo]()
$258
This United Airlines deal was found by Cheapflights users on 5/11. 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 6/205:57 pm
CRW
- ORD
Nonstop2h 04m
United Airlines
Sun 6/217:35 am
ORD
- CRW
Nonstop1h 50m
United Airlines
Deal found 5/11![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 5/14. 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.
Fri 7/315:45 am
PIT
- MDW
2 stops8h 40m
Southwest
Tue 8/46:20 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 5/14![Southwest logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Thu 9/107:30 am
PIT
- RFD
1 stop26h 22m
Allegiant Air
Sun 9/133:53 pm
RFD
- PIT
1 stop6h 00m
Allegiant Air
Deal found 5/10![Allegiant Air logo]()
$343
This Delta deal was found by Cheapflights users on 5/10. 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.
Thu 7/26:00 am
IAD
- MDW
1 stop4h 14m
Delta
Wed 7/86:00 am
MDW
- IAD
1 stop4h 37m
Delta
Deal found 5/10![Delta logo]()
$258
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:20 pm
IAD
- ORD
Nonstop2h 11m
United Airlines
Tue 6/309:40 pm
ORD
- IAD
Nonstop2h 05m
United Airlines
Deal found 5/13![United Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:50 pm
HTS
- ORD
1 stop5h 08m
American Airlines
Sat 6/204:49 pm
ORD
- HTS
1 stop6h 07m
American Airlines
Deal found 5/13![American Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 5/11. 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 6/156:00 am
IAD
- MDW
1 stop5h 09m
Delta
Wed 6/179:17 am
MDW
- IAD
1 stop6h 25m
Delta
Deal found 5/11![Delta logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Fri 7/39:18 pm
PIT
- RFD
1 stop12h 57m
Allegiant Air
Sun 7/59:19 am
RFD
- PIT
1 stop12h 39m
Allegiant Air
Deal found 5/10![Allegiant Air logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/10. 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 7/115:42 pm
IAD
- ORD
Nonstop2h 08m
United Airlines
Tue 7/146:30 am
ORD
- IAD
Nonstop1h 54m
United Airlines
Deal found 5/10![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 5/11. 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 6/96:00 am
CRW
- MDW
1 stop5h 09m
Delta
Tue 6/235:11 pm
MDW
- CRW
1 stop5h 20m
Delta
Deal found 5/11![Delta logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Thu 5/2812:45 pm
PIT
- RFD
1 stop20h 00m
Allegiant Air
Thu 6/49:19 am
RFD
- PIT
1 stop12h 45m
Allegiant Air
Deal found 5/14![Allegiant Air logo]()
$353
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/2510:20 pm
IAD
- ORD
Nonstop2h 11m
United Airlines
Wed 7/16:30 am
ORD
- IAD
Nonstop1h 54m
United Airlines
Deal found 5/12![United Airlines logo]()
$247
Last-minute flights from West Virginia to ChicagoDiscover last-minute flight deals from West Virginia to Chicago. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from West Virginia to Chicago. Data last updated May 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/11. 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 6/18:00 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sat 6/66:30 am
MDW
- PIT
1 stop5h 40m
Southwest
Deal found 5/11![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 5/11. 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 6/15:40 am
PIT
- MDW
1 stop5h 20m
Delta
Sat 6/66:36 pm
MDW
- PIT
1 stop2h 46m
Delta
Deal found 5/11![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 5/11. 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 6/16:25 pm
PIT
- ORD
1 stop6h 34m
Delta
Sat 6/65:19 pm
ORD
- PIT
1 stop4h 03m
Delta
Deal found 5/11![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/12. 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 6/24:10 pm
PIT
- ORD
Nonstop1h 51m
United Airlines
Wed 6/310:29 am
ORD
- PIT
Nonstop1h 42m
United Airlines
Deal found 5/12![United Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:59 am
PIT
- ORD
Nonstop2h 01m
American Airlines
Mon 6/85:00 am
ORD
- PIT
1 stop5h 57m
American Airlines
Deal found 5/13![American Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 5/10. 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 6/36:40 am
PIT
- MDW
2 stops10h 10m
Southwest
Mon 6/82:45 pm
MDW
- PIT
1 stop6h 45m
Southwest
Deal found 5/10![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:31 am
PIT
- MDW
1 stop3h 11m
Delta
Mon 6/86:58 pm
MDW
- PIT
1 stop4h 09m
Delta
Deal found 5/13![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:00 pm
PIT
- ORD
1 stop6h 05m
Delta
Mon 6/87:17 pm
ORD
- PIT
1 stop3h 50m
Delta
Deal found 5/13![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/43:50 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Mon 6/86:50 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:25 pm
PIT
- MDW
1 stop6h 00m
Southwest
Tue 6/96:10 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 5/13![Southwest logo]()
$192
This KAYAK deal was found by Cheapflights users on 5/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:56 pm
PIT
- ORD
Nonstop1h 51m
American Airlines
Wed 6/104:50 pm
ORD
- PIT
Nonstop1h 38m
American Airlines
Deal found 5/14![American Airlines logo]()
$202
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/112:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Wed 6/174:35 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 5/12![United Airlines logo]()
$194
One-way flights from West Virginia to ChicagoSearch for one-way flight options from West Virginia to Chicago. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
Search for one-way flight options from West Virginia to Chicago. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:30 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Deal found 5/13![Southwest logo]()
$59
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/213:59 pm
PIT
- ORD
Nonstop1h 51m
American Airlines
Deal found 5/13![American Airlines logo]()
$59
This United Airlines deal was found by Cheapflights users on 5/15. 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.
Wed 7/157:00 am
PIT
- ORD
Nonstop1h 48m
United Airlines
Deal found 5/15![United Airlines logo]()
$69
This Southwest deal was found by Cheapflights users on 5/12. 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 7/76:30 am
PIT
- MDW
2 stops8h 05m
Southwest
Deal found 5/12![Southwest logo]()
$74
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:10 am
PIT
- MDW
1 stop7h 06m
Delta
Deal found 5/13![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:20 pm
PIT
- ORD
1 stop6h 39m
Delta
Deal found 5/13![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 5/12. 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 8/410:10 am
PIT
- MDW
2 stops9h 55m
Southwest
Deal found 5/12![Southwest logo]()
$80
This Southwest deal was found by Cheapflights users on 5/12. 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 8/177:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 5/12![Southwest logo]()
$89
This United Airlines deal was found by Cheapflights users on 5/11. 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 6/610:54 am
PIT
- ORD
Nonstop1h 48m
United Airlines
Deal found 5/11![United Airlines logo]()
$89
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:10 pm
PIT
- ORD
Nonstop1h 51m
United Airlines
Deal found 5/13![United Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1011:17 am
IAD
- ORD
1 stop9h 33m
Frontier
Deal found 5/15![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 5/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:25 pm
IAD
- ORD
1 stop19h 00m
Frontier
Deal found 5/12![Frontier logo]()
$97
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 May 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $187 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $359 |
Good round-trip deal | $368 or less |
Good one-way deal | $148 or less |
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 May 15, 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
Cheapest round-trip
ClarksburgChicago
CKB - ORD
CKBORD
Clarksburg Benedum
Thu 6/11
2:25 pm-3:19 pm
Nonstop1h 54m
Chicago O'Hare Intl
Wed 6/17
4:35 pm-7:23 pm
Nonstop1h 48m
$194
ClarksburgChicago
CKB - ORD
CKBORD
Clarksburg Benedum
Fri 6/19
2:25 pm-3:19 pm
Nonstop1h 54m
Chicago O'Hare Intl
Mon 6/22
4:35 pm-7:23 pm
Nonstop1h 48m
$194
ClarksburgChicago
CKB - ORD
CKBORD
Clarksburg Benedum
Thu 7/9
2:25 pm-3:19 pm
Nonstop1h 54m
Chicago O'Hare Intl
Tue 7/14
4:41 pm-7:29 pm
Nonstop1h 48m
$194
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sat 6/13
6:20 pm-10:17 pm
1 stop4h 57m
Chicago Midway
Mon 6/15
6:58 pm-12:07 am
1 stop4h 09m
$197
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Thu 6/4
10:31 am-1:01 pm
1 stop3h 30m
Chicago O'Hare Intl
Mon 6/8
7:17 pm-12:07 am
1 stop3h 50m
$197
LewisburgChicago
LWB - ORD
LWBORD
Lewisburg Greenbrier Valley
Fri 6/5
4:26 pm-5:35 pm
Nonstop2h 09m
Chicago O'Hare Intl
Mon 6/8
3:08 pm-6:02 pm
Nonstop1h 54m
$214
LewisburgChicago
LWB - ORD
LWBORD
Lewisburg Greenbrier Valley
Sun 6/7
4:26 pm-5:35 pm
Nonstop2h 09m
Chicago O'Hare Intl
Sat 6/13
3:06 pm-6:00 pm
Nonstop1h 54m
$214
LewisburgChicago
LWB - ORD
LWBORD
Lewisburg Greenbrier Valley
Wed 6/3
4:26 pm-5:33 pm
Nonstop2h 07m
Chicago O'Hare Intl
Sat 6/6
3:06 pm-6:00 pm
Nonstop1h 54m
$214
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Mon 6/8
3:50 pm-4:20 pm
Nonstop1h 30m
Chicago Midway
Wed 6/10
7:50 am-10:20 am
Nonstop1h 30m
$217
CharlestonChicago
CRW - ORD
CRWORD
Charleston Yeager
Wed 6/10
11:00 am-11:58 am
Nonstop1h 58m
Chicago O'Hare Intl
Wed 6/17
5:50 pm-8:42 pm
Nonstop1h 52m
$239
Showing 1-10 of 60 resultsSorted by cheapest first
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.
PIT-MDW
PIT-ORD
IAD-MDW
LWB-ORD
HTS-ORD
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
USWV-CHI
PIT-MDW
PIT-ORD
IAD-MDW
LWB-ORD
What is the cheapest month to book a flight from West Virginia to Chicago?
Currently, June is the cheapest month in which you can book a flight from West Virginia to Chicago (average of $163). 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 May 15, 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 May 9, 2026.
Travelers seeking maximum savings on their West Virginia to Chicago flight should consider departing on Friday evenings 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 May 15, 2026.
The most flights from USWV to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes
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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.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 15, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from West Virginia to Chicago by cabin class
Find flights from West Virginia to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
West Virginia and Chicago flights
Browse other West Virginia and Chicago flight options. Last updated on May 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
West Virginia to Chicago flights
Consider these flights traveling from West Virginia to Chicago.
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 May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$145 | Average$309 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$218 | Average$218 | FlexibilityNo cancel fee | On-time71% |