$69+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Aug 12 — Aug 191
Round-trip
1 adult, Economy
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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 July 13, 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 July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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.
Sat 8/226:10 am
PIT
- MDW
2 stops7h 55m
Southwest
Tue 8/252:00 pm
MDW
- PIT
2 stops6h 30m
Southwest
Deal found 7/10![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 7/10. 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 8/66:10 am
PIT
- MDW
2 stops10h 15m
Southwest
Mon 8/1010:30 am
MDW
- PIT
1 stop6h 10m
Southwest
Deal found 7/10![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 7/11. 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.
Sat 8/86:50 am
PIT
- MDW
1 stop3h 40m
Southwest
Sat 8/157:45 am
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/11![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 7/11. 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 8/106:10 am
PIT
- MDW
2 stops10h 15m
Southwest
Wed 8/121:00 pm
MDW
- PIT
2 stops7h 30m
Southwest
Deal found 7/11![Southwest logo]()
$173
This Southwest deal was found by Cheapflights users on 7/11. 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.
Thu 9/34:10 pm
PIT
- MDW
1 stop4h 05m
Southwest
Mon 9/77:55 am
MDW
- PIT
1 stop4h 15m
Southwest
Deal found 7/11![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 7/9. 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 8/12:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Tue 8/44:42 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 7/9![United Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 7/10. 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.
Tue 8/1812:40 pm
PIT
- MDW
2 stops10h 10m
Southwest
Thu 8/201:00 pm
MDW
- PIT
1 stop3h 40m
Southwest
Deal found 7/10![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 7/10. 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.
Tue 11/177:45 pm
PIT
- ORD
Nonstop1h 54m
United Airlines
Wed 11/187:15 am
ORD
- PIT
Nonstop1h 38m
United Airlines
Deal found 7/10![United Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Fri 9/411:21 am
PIT
- ORD
Nonstop1h 53m
American Airlines
Mon 9/712:39 pm
ORD
- PIT
Nonstop1h 37m
American Airlines
Deal found 7/10![American Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 7/10. 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.
Fri 9/47:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 9/77:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/10![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Sat 8/225:21 am
PIT
- ORD
Nonstop1h 49m
American Airlines
Thu 8/279:56 am
ORD
- PIT
1 stop7h 30m
American Airlines
Deal found 7/11![American Airlines logo]()
$210
This American Airlines deal was found by Cheapflights users on 7/10. 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 8/94:16 pm
LWB
- ORD
Nonstop2h 11m
American Airlines
Fri 8/213:28 pm
ORD
- LWB
Nonstop1h 53m
American Airlines
Deal found 7/10![American Airlines logo]()
$214
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 July 13, 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 July 13, 2026.
This United Airlines deal was found by Cheapflights users on 7/11. 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 8/12:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Tue 8/44:42 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 7/11![United Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 7/10. 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 8/94:16 pm
LWB
- ORD
Nonstop2h 11m
American Airlines
Fri 8/213:28 pm
ORD
- LWB
Nonstop1h 53m
American Airlines
Deal found 7/10![American Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 7/7. 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 8/67:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 8/107:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/7![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am
PIT
- ORD
1 stop5h 19m
Delta
Mon 9/215:10 pm
ORD
- PIT
1 stop5h 48m
Delta
Deal found 7/12![Delta logo]()
$218
This JetBlue deal was found by Cheapflights users on 7/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:20 pm
PIT
- ORD
1 stop7h 02m
JetBlue
Sat 9/263:00 pm
ORD
- PIT
1 stop7h 20m
JetBlue
Deal found 7/9![JetBlue logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:00 am
PIT
- RFD
1 stop8h 09m
Multiple Airlines
Mon 8/316:04 pm
RFD
- PIT
1 stop16h 17m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/612:45 pm
PIT
- RFD
1 stop20h 04m
Allegiant Air
Sun 8/99:21 am
RFD
- PIT
1 stop12h 49m
Allegiant Air
Deal found 7/12![Allegiant Air logo]()
$345
This Southwest deal was found by Cheapflights users on 7/9. 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 8/52:00 pm
PIT
- MDW
Nonstop1h 25m
Southwest
Mon 8/107:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/9![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/9. 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 8/82:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Tue 8/119:20 pm
ORD
- CKB
Nonstop1h 49m
United Airlines
Deal found 7/9![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 7/10. 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 9/512:30 pm
PIT
- ORD
1 stop7h 43m
Delta
Tue 9/85:30 am
ORD
- PIT
1 stop7h 06m
Delta
Deal found 7/10![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 7/8. 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 9/128:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Thu 9/177:55 am
MDW
- PIT
1 stop4h 15m
Southwest
Deal found 7/8![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 7/9. 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 8/510:30 am
PIT
- ORD
1 stop7h 07m
Delta
Mon 8/107:30 pm
ORD
- PIT
1 stop3h 34m
Delta
Deal found 7/9![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Wed 9/2310:16 am
PIT
- ORD
Nonstop1h 54m
American Airlines
Sun 9/275:48 pm
ORD
- PIT
1 stop4h 48m
American Airlines
Deal found 7/12![American Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 7/7. 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 8/87:00 am
CRW
- ORD
Nonstop2h 00m
United Airlines
Sun 8/167:00 am
ORD
- CRW
Nonstop1h 54m
United Airlines
Deal found 7/7![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 7/8. 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 10/146:00 am
PIT
- ORD
1 stop5h 39m
Delta
Sat 10/177:00 am
ORD
- PIT
1 stop6h 38m
Delta
Deal found 7/8![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/11. 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 8/87:00 am
CRW
- ORD
Nonstop2h 00m
United Airlines
Sat 8/157:00 am
ORD
- CRW
Nonstop1h 54m
United Airlines
Deal found 7/11![United Airlines logo]()
$239
This JetBlue deal was found by Cheapflights users on 7/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am
PIT
- ORD
1 stop8h 01m
JetBlue
Sun 10/43:00 pm
ORD
- PIT
1 stop7h 20m
JetBlue
Deal found 7/10![JetBlue logo]()
$300
This United Airlines deal was found by Cheapflights users on 7/12. 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 9/36:15 am
IAD
- ORD
Nonstop2h 15m
United Airlines
Fri 9/412:56 pm
ORD
- IAD
Nonstop2h 06m
United Airlines
Deal found 7/12![United Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 7/11. 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.
Thu 9/106:10 am
PIT
- MDW
2 stops10h 15m
Southwest
Sun 9/138:50 am
MDW
- PIT
2 stops5h 30m
Southwest
Deal found 7/11![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 7/11. 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 8/84:55 pm
PIT
- ORD
1 stop8h 02m
Delta
Sat 8/156:40 am
ORD
- PIT
1 stop5h 12m
Delta
Deal found 7/11![Delta logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/612:45 pm
PIT
- RFD
1 stop20h 04m
Multiple Airlines
Mon 8/106:26 pm
RFD
- PIT
2 stops17h 29m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Tue 7/2810:00 am
PIT
- RFD
1 stop25h 29m
Allegiant Air
Thu 7/309:19 am
RFD
- PIT
1 stop12h 39m
Allegiant Air
Deal found 7/12![Allegiant Air logo]()
$370
This Delta deal was found by Cheapflights users on 7/8. 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 9/246:53 pm
CRW
- ORD
1 stop6h 06m
Delta
Sun 9/275:30 am
ORD
- CRW
1 stop7h 22m
Delta
Deal found 7/8![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 7/12. 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.
Thu 8/67:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Sun 8/96:50 am
MDW
- PIT
1 stop6h 40m
Southwest
Deal found 7/12![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 10/19:00 am
PIT
- RFD
1 stop6h 26m
Multiple Airlines
Sun 10/411:12 am
RFD
- PIT
2 stops23h 33m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 7/8. 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 7/292:25 pm
CKB
- ORD
Nonstop1h 54m
United Airlines
Sat 8/14:42 pm
ORD
- CKB
Nonstop1h 48m
United Airlines
Deal found 7/8![United Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:30 pm
PIT
- ORD
1 stop8h 03m
Delta
Tue 11/102:30 pm
ORD
- PIT
1 stop5h 56m
Delta
Deal found 7/12![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 7/9. 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 7/307:00 am
CRW
- ORD
Nonstop2h 00m
United Airlines
Sun 8/25:55 pm
ORD
- CRW
Nonstop1h 52m
United Airlines
Deal found 7/9![United Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 9/43:15 pm
PIT
- RFD
1 stop21h 36m
Multiple Airlines
Mon 9/76:02 pm
RFD
- PIT
1 stop16h 19m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 7/266:06 pm
PIT
- RFD
1 stop14h 43m
Allegiant Air
Thu 7/309:19 am
RFD
- PIT
1 stop12h 39m
Allegiant Air
Deal found 7/7![Allegiant Air logo]()
$421
Last-minute flights from West Virginia to ChicagoDiscover last-minute flight deals from West Virginia to Chicago. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from West Virginia to Chicago. Data last updated July 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Tue 8/49:55 am
PIT
- ORD
Nonstop1h 47m
American Airlines
Fri 8/79:15 pm
ORD
- PIT
Nonstop1h 44m
American Airlines
Deal found 7/10![American Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 7/10. 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 8/66:10 am
PIT
- MDW
2 stops10h 15m
Southwest
Mon 8/1010:30 am
MDW
- PIT
1 stop6h 10m
Southwest
Deal found 7/10![Southwest logo]()
$168
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/610:54 am
PIT
- ORD
Nonstop1h 48m
United Airlines
Sat 8/83:46 pm
ORD
- PIT
Nonstop1h 49m
United Airlines
Deal found 7/8![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 7/11. 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.
Sat 8/86:50 am
PIT
- MDW
1 stop3h 40m
Southwest
Sat 8/157:45 am
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/11![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/84:55 pm
PIT
- MDW
1 stop6h 41m
Delta
Sat 8/156:42 pm
MDW
- PIT
1 stop3h 09m
Delta
Deal found 7/12![Delta logo]()
$218
This American Airlines deal was found by Cheapflights users on 7/10. 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 8/94:16 pm
LWB
- ORD
Nonstop2h 11m
American Airlines
Fri 8/213:28 pm
ORD
- LWB
Nonstop1h 53m
American Airlines
Deal found 7/10![American Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 7/11. 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 8/106:10 am
PIT
- MDW
2 stops10h 15m
Southwest
Wed 8/121:00 pm
MDW
- PIT
2 stops7h 30m
Southwest
Deal found 7/11![Southwest logo]()
$173
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Mon 8/178:59 pm
PIT
- ORD
Nonstop2h 01m
American Airlines
Thu 8/209:56 am
ORD
- PIT
1 stop7h 30m
American Airlines
Deal found 7/10![American Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 7/10. 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.
Tue 8/1812:40 pm
PIT
- MDW
2 stops10h 10m
Southwest
Thu 8/201:00 pm
MDW
- PIT
1 stop3h 40m
Southwest
Deal found 7/10![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 7/10. 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.
Fri 8/218:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Tue 8/258:45 am
MDW
- PIT
Nonstop1h 35m
Southwest
Deal found 7/10![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 7/10. 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.
Sat 8/226:10 am
PIT
- MDW
2 stops7h 55m
Southwest
Tue 8/252:00 pm
MDW
- PIT
2 stops6h 30m
Southwest
Deal found 7/10![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Sat 8/225:21 am
PIT
- ORD
Nonstop1h 49m
American Airlines
Thu 8/279:56 am
ORD
- PIT
1 stop7h 30m
American Airlines
Deal found 7/10![American Airlines logo]()
$214
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 July 13, 2026.
Search for one-way flight options from West Virginia to Chicago. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 8/56:55 pm
PIT
- MDW
Nonstop1h 25m
Southwest
Deal found 7/10![Southwest logo]()
$69
This United Airlines deal was found by Cheapflights users on 7/10. 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 9/245:11 am
PIT
- ORD
Nonstop1h 48m
United Airlines
Deal found 7/10![United Airlines logo]()
$69
This Delta deal was found by Cheapflights users on 7/11. 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.
Wed 8/511:57 am
PIT
- ORD
1 stop7h 52m
Delta
Deal found 7/11![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 7/11. 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.
Sat 8/156:10 am
PIT
- MDW
2 stops7h 55m
Southwest
Deal found 7/11![Southwest logo]()
$84
This Southwest deal was found by Cheapflights users on 7/11. 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 8/106:10 am
PIT
- MDW
2 stops10h 15m
Southwest
Deal found 7/11![Southwest logo]()
$90
This Delta deal was found by Cheapflights users on 7/11. 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 8/226:10 am
IAD
- ORD
1 stop5h 32m
Delta
Deal found 7/11![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 7/11. 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 8/116:00 am
IAD
- MDW
1 stop6h 51m
Delta
Deal found 7/11![Delta logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Mon 8/36:09 pm
IAD
- ORD
1 stop19h 06m
Frontier
Deal found 7/10![Frontier logo]()
$100
This Delta deal was found by Cheapflights users on 7/8. 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 8/45:47 pm
IAD
- ORD
1 stop7h 10m
Delta
Deal found 7/8![Delta logo]()
$101
This Delta deal was found by Cheapflights users on 7/8. 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 8/275:47 pm
IAD
- MDW
1 stop5h 49m
Delta
Deal found 7/8![Delta logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Sat 8/227:00 am
IAD
- MDW
1 stop16h 47m
Frontier
Deal found 7/8![Frontier logo]()
$102
This Delta deal was found by Cheapflights users on 7/9. 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 10/315:08 pm
IAD
- ORD
1 stop4h 22m
Delta
Deal found 7/9![Delta logo]()
$103
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 July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $167 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $482 |
Good round-trip deal | $283 or less |
Good one-way deal | $127 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 July 13, 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
Sat 8/1
2:25 pm-3:19 pm
Nonstop1h 54m
Chicago O'Hare Intl
Tue 8/4
4:42 pm-7:30 pm
Nonstop1h 48m
$194
LewisburgChicago
LWB - ORD
LWBORD
Lewisburg Greenbrier Valley
Sun 8/9
4:16 pm-5:27 pm
Nonstop2h 11m
Chicago O'Hare Intl
Fri 8/21
3:28 pm-6:21 pm
Nonstop1h 53m
$214
Quickest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Thu 8/6
7:30 pm-7:50 pm
Nonstop1h 20m
Chicago Midway
Mon 8/10
7:40 pm-10:05 pm
Nonstop1h 25m
$217
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Wed 8/5
2:00 pm-2:25 pm
Nonstop1h 25m
Chicago Midway
Mon 8/10
7:40 pm-10:05 pm
Nonstop1h 25m
$217
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Thu 9/17
6:00 am-10:19 am
1 stop5h 19m
Chicago O'Hare Intl
Mon 9/21
5:10 pm-11:58 pm
1 stop5h 48m
$218
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sat 9/12
8:40 am-9:00 am
Nonstop1h 20m
Chicago Midway
Thu 9/17
7:55 am-1:10 pm
1 stop4h 15m
$227
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Tue 9/22
1:20 pm-7:22 pm
1 stop7h 02m
Chicago O'Hare Intl
Sat 9/26
3:00 pm-11:20 pm
1 stop7h 20m
$230
ClarksburgChicago
CKB - ORD
CKBORD
Clarksburg Benedum
Sat 8/8
2:25 pm-3:19 pm
Nonstop1h 54m
Chicago O'Hare Intl
Tue 8/11
9:20 pm-12:09 am
Nonstop1h 49m
$234
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Sat 9/5
12:30 pm-7:13 pm
1 stop7h 43m
Chicago O'Hare Intl
Tue 9/8
5:30 am-1:36 pm
1 stop7h 06m
$237
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Wed 8/5
10:30 am-4:37 pm
1 stop7h 07m
Chicago O'Hare Intl
Mon 8/10
7:30 pm-12:04 am
1 stop3h 34m
$237
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.
CKB-ORD
LWB-ORD
PIT-MDW
PIT-ORD
PIT-RFD
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
CKB-ORD
LWB-ORD
PIT-MDW
PIT-ORD
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 $178). Flying from West Virginia to Chicago in November is currently the most expensive (average of $278). 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 13, 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 at noon, which can drop the price by up to 7% versus a flight in the morning.
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 13, 2026.
The most flights from USWV to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, 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?
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 July 11, 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.
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
Valparaiso
Hammond
Saint Joseph
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 July 13, 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 July 13, 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 July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$145 | Average$324 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$218 | Average$268 | FlexibilityNo cancel fee | On-time71% |