$176+ Cheap flights from Charleston, WV (CRW) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Sep 16 — Sep 231
Round-trip
1 adult, Economy
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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
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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 Charleston to Chicago
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Cheapest flights from Charleston to ChicagoExplore the most affordable flight options available from Charleston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
Explore the most affordable flight options available from Charleston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 12/54:35 pm -
1 stop7h 21m
Tue 12/811:28 am -
1 stop5h 50m
Deal found 8/13![Delta logo]()
$176
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 12/511:10 am -
1 stop4h 28m
Tue 12/85:30 am -
1 stop7h 25m
Deal found 8/13![Delta logo]()
$176
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 12/76:00 am -
1 stop7h 05m
Tue 1/55:25 pm -
1 stop4h 14m
Deal found 8/13![Delta logo]()
$189
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 12/711:10 am -
1 stop6h 53m
Tue 1/59:30 am -
1 stop4h 11m
Deal found 8/13![Delta logo]()
$189
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 12/511:10 am -
1 stop5h 09m
Mon 12/75:09 pm -
1 stop5h 24m
Deal found 8/13![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 12/511:10 am -
1 stop6h 53m
Mon 12/79:53 am -
1 stop7h 25m
Deal found 8/13![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 8/13. 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 12/811:10 am -
1 stop4h 28m
Thu 12/311:35 pm -
2 stops8h 04m
Deal found 8/13![Delta logo]()
$195
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 12/711:10 am -
1 stop6h 04m
Mon 1/45:25 pm -
1 stop4h 14m
Deal found 8/13![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 8/14. 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 11/1211:10 am -
1 stop6h 53m
Sun 11/156:45 am -
1 stop6h 10m
Deal found 8/14![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 12/116:58 pm -
1 stop4h 58m
Mon 1/45:25 pm -
1 stop4h 14m
Deal found 8/13![Delta logo]()
$206
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Thu 9/2412:45 pm -
1 stop5h 53m
Sun 9/275:18 am -
1 stop4h 07m
Deal found 8/15![American Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 12/711:10 am -
1 stop4h 28m
Thu 12/311:35 pm -
2 stops8h 04m
Deal found 8/13![Delta logo]()
$208
Best flights from Charleston to ChicagoDiscover carefully curated flight deals from Charleston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
Discover carefully curated flight deals from Charleston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sun 9/136:05 pm -
Nonstop1h 57m
Sun 9/208:59 pm -
Nonstop1h 49m
Deal found 8/14![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 9/1012:45 pm -
1 stop5h 53m
Wed 9/168:59 am -
1 stop5h 55m
Deal found 8/12![American Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 8/17. 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 12/511:10 am -
2 stops7h 54m
Mon 12/76:00 am -
1 stop6h 55m
Deal found 8/17![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/107:00 am -
Nonstop1h 57m
Sat 9/126:30 am -
Nonstop1h 52m
Deal found 8/12![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/106:05 pm -
Nonstop1h 57m
Wed 9/169:10 pm -
Nonstop1h 49m
Deal found 8/12![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 8/17. 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 12/511:10 am -
2 stops7h 54m
Tue 12/81:22 pm -
2 stops9h 11m
Deal found 8/17![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/116:05 pm -
Nonstop1h 57m
Fri 9/186:30 am -
Nonstop1h 52m
Deal found 8/13![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Fri 9/116:05 pm -
Nonstop1h 57m
Sat 9/129:10 pm -
Nonstop1h 49m
Deal found 8/15![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 8/17. 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 9/14:48 pm -
1 stop6h 48m
Sat 9/54:39 pm -
1 stop4h 21m
Deal found 8/17![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:20 am -
Nonstop2h 00m
Mon 9/218:59 pm -
Nonstop1h 49m
Deal found 8/16![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 8/294:48 pm -
1 stop6h 48m
Wed 9/24:39 pm -
1 stop5h 52m
Deal found 8/14![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/46:05 pm -
Nonstop2h 00m
Mon 9/77:00 am -
Nonstop1h 54m
Deal found 8/13![United Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 9/126:05 pm -
Nonstop1h 57m
Sun 9/138:59 pm -
Nonstop1h 49m
Deal found 8/14![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:50 pm -
Nonstop2h 05m
Thu 11/2610:25 am -
Nonstop1h 48m
Deal found 8/16![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/12. 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 11/206:58 pm -
1 stop4h 58m
Fri 11/274:19 pm -
1 stop20h 36m
Deal found 8/12![Delta logo]()
$475
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Mon 9/216:05 pm -
Nonstop1h 57m
Mon 9/286:51 am -
Nonstop1h 52m
Deal found 8/15![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:54 pm -
1 stop4h 50m
Mon 9/215:10 pm -
1 stop5h 10m
Deal found 8/16![Delta logo]()
$513
This Delta deal was found by Cheapflights users on 8/14. 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 10/146:00 am -
2 stops7h 47m
Thu 10/151:27 pm -
2 stops9h 03m
Deal found 8/14![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 8/12. 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 8/286:46 pm -
1 stop4h 50m
Tue 9/11:51 pm -
2 stops8h 40m
Deal found 8/12![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am -
1 stop4h 59m
Fri 8/285:10 pm -
1 stop16h 17m
Deal found 8/16![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 8/14. 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 9/36:00 am -
1 stop6h 51m
Fri 9/114:30 pm -
1 stop4h 22m
Deal found 8/14![Delta logo]()
$693
Last-minute flights from Charleston to ChicagoDiscover last-minute flight deals from Charleston to Chicago. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Chicago. Data last updated August 17, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/12. 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 8/277:02 am -
Nonstop1h 57m
Sun 8/307:00 am -
Nonstop1h 54m
Deal found 8/12![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 8/275:14 pm -
1 stop7h 38m
Sun 8/307:30 am -
1 stop6h 30m
Deal found 8/12![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/2810:25 am -
1 stop4h 57m
Mon 8/314:53 pm -
1 stop5h 06m
Deal found 8/12![American Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/46:05 pm -
Nonstop2h 00m
Mon 9/77:00 am -
Nonstop1h 54m
Deal found 8/13![United Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:45 am -
Nonstop2h 00m
Mon 9/77:00 am -
Nonstop1h 54m
Deal found 8/16![United Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 9/1012:45 pm -
1 stop5h 53m
Wed 9/168:59 am -
1 stop5h 55m
Deal found 8/12![American Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/102:43 pm -
2 stops46h 08m
Wed 9/163:50 pm -
1 stop16h 29m
Deal found 8/12![Multiple Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/116:05 pm -
Nonstop1h 57m
Fri 9/186:30 am -
Nonstop1h 52m
Deal found 8/13![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Fri 9/114:24 pm -
1 stop7h 07m
Sat 9/125:20 am -
1 stop5h 45m
Deal found 8/15![American Airlines logo]()
$252
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:20 am -
Nonstop2h 00m
Mon 9/218:59 pm -
Nonstop1h 49m
Deal found 8/16![United Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Thu 9/2412:45 pm -
1 stop5h 53m
Sun 9/275:18 am -
1 stop4h 07m
Deal found 8/15![American Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 8/12. 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 9/246:54 pm -
1 stop6h 05m
Sun 9/275:30 am -
1 stop7h 23m
Deal found 8/12![Delta logo]()
$216
One-way flights from Charleston to ChicagoSearch for one-way flight options from Charleston to Chicago. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
Search for one-way flight options from Charleston to Chicago. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:08 pm -
1 stop5h 53m
Deal found 8/14![American Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Mon 8/2410:59 am -
2 stops12h 48m
Deal found 8/14![Multiple Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 8/13. 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 8/286:20 am -
1 stop6h 55m
Deal found 8/13![American Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:59 am -
2 stops26h 51m
Deal found 8/13![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:22 pm -
3 stops23h 28m
Deal found 8/14![Multiple Airlines logo]()
$232
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 11/71:50 pm -
Nonstop2h 03m
Deal found 8/14![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 11/711:11 am -
1 stop5h 06m
Deal found 8/14![Delta logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:22 pm -
3 stops33h 25m
Deal found 8/14![Multiple Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 11/711:11 am -
2 stops10h 19m
Deal found 8/14![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:02 am -
Nonstop2h 03m
Deal found 8/16![United Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Sat 8/222:22 pm -
3 stops26h 38m
Deal found 8/12![Multiple Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Sat 8/2210:25 am -
1 stop7h 25m
Deal found 8/12![American Airlines logo]()
$306
Find flight deals from Charleston to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CRW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Delta) |
Popular in | July |
Cheapest in | February |
Average price | $393 |
Good round-trip deal | $363 or less |
Good one-way deal | $389 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Charleston 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 August 17, 2026.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.
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Quickest round-trip
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Sun 9/13
6:05 pm-7:02 pm
Nonstop1h 57m
Chicago O'Hare Intl
Sun 9/20
8:59 pm-11:48 pm
Nonstop1h 49m
$249
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Thu 9/10
7:00 am-7:57 am
Nonstop1h 57m
Chicago O'Hare Intl
Sat 9/12
6:30 am-9:22 am
Nonstop1h 52m
$249
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Thu 9/10
6:05 pm-7:02 pm
Nonstop1h 57m
Chicago O'Hare Intl
Wed 9/16
9:10 pm-11:59 pm
Nonstop1h 49m
$249
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 9/11
6:05 pm-7:02 pm
Nonstop1h 57m
Chicago O'Hare Intl
Fri 9/18
6:30 am-9:22 am
Nonstop1h 52m
$249
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 9/11
6:05 pm-7:02 pm
Nonstop1h 57m
Chicago O'Hare Intl
Sat 9/12
9:10 pm-11:59 pm
Nonstop1h 49m
$249
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Thu 9/10
12:45 pm-5:38 pm
1 stop5h 53m
Chicago O'Hare Intl
Wed 9/16
8:59 am-3:54 pm
1 stop5h 55m
$268
CharlestonChicago
CRW Charleston Yeager - MDW Chicago Midway
CRWMDW
Charleston Yeager
Sat 12/5
11:10 am-6:04 pm
2 stops7h 54m
Chicago Midway
Mon 12/7
6:00 am-1:55 pm
1 stop6h 55m
$274
CharlestonChicago
CRW Charleston Yeager - MDW Chicago Midway
CRWMDW
Charleston Yeager
Sat 12/5
11:10 am-6:04 pm
2 stops7h 54m
Chicago Midway
Tue 12/8
1:22 pm-11:33 pm
2 stops9h 11m
$279
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Tue 9/15
10:20 am-11:20 am
Nonstop2h 00m
Chicago O'Hare Intl
Mon 9/21
8:59 pm-11:48 pm
Nonstop1h 49m
$281
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 9/4
6:05 pm-7:05 pm
Nonstop2h 00m
Chicago O'Hare Intl
Mon 9/7
7:00 am-9:54 am
Nonstop1h 54m
$293
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Charleston to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Charleston to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Charleston, West Virginia-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charleston, West Virginia-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charleston, West Virginia-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Charleston, West Virginia-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charleston, West Virginia-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Charleston to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Charleston with our price prediction graph.
CRW-CHI
CRW-ORD
CRW-MDW
CRW-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 Charleston to Chicago
CRW-CHI
CRW-ORD
CRW-MDW
CRW-RFD
What is the cheapest month to book a flight from Charleston, West Virginia to Chicago?
Currently, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $250). Flying from Charleston, West Virginia to Chicago in November is currently the most expensive (average of $379). 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 CRW to CHI?
Find hourly flight availability from Charleston 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 August 17, 2026.
It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the morning.
Weekly flight availability from Charleston, West Virginia to Chicago
Explore weekly flight availability from Charleston 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 August 17, 2026.
The most flights from CRW to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Charleston, West Virginia to Chicago?
Airfare is below average for this route at the moment.
Charleston, West Virginia to Chicago flights typically cost between $253 and $401 in December.The cheapest round-trip price found within the last 5 days was $176 on Delta (Dec 5-Dec 8).
What is the cheapest day to fly from Charleston, West Virginia to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Charleston to Chicago. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Charleston, 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.
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 August 17, 2026.
Read through reviews of airlines operating flights from Charleston to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Crew
8.1
Food
6.7
Boarding
7.7
Overall
7.4
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Crew
8.1
Food
6.7
Boarding
7.7
Overall
7.4
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Charleston 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
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Other flights to Chicago
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Charleston and Chicago flights
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Other flights from Charleston
Browse through other flights departing from Charleston. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Charleston to Chicago
Discover the top airline that operate flights from Charleston 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 August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$304 | FlexibilityNo cancel fee | On-time69% |