$208+ 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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Charleston to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 October 30, 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 October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/247:16 pm -
1 stop5h 43m
Thu 12/38:10 am -
1 stop5h 16m
Deal found 10/28![American Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/245:00 am -
1 stop4h 59m
Mon 11/306:49 pm -
1 stop4h 14m
Deal found 10/27![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/215:00 am -
1 stop5h 00m
Fri 11/275:19 am -
1 stop5h 01m
Deal found 10/28![American Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/246:02 am -
Nonstop2h 03m
Mon 11/309:15 pm -
Nonstop1h 44m
Deal found 10/27![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/241:50 pm -
Nonstop2h 05m
Sat 11/2810:25 am -
Nonstop1h 48m
Deal found 10/29![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 10/26. 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 11/214:48 pm -
1 stop7h 06m
Thu 11/264:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/26. 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 11/236:00 am -
1 stop7h 20m
Thu 11/262:00 pm -
1 stop7h 19m
Deal found 10/26![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/27. 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 11/246:00 am -
2 stops8h 59m
Sat 11/285:30 am -
1 stop4h 10m
Deal found 10/27![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/101:50 pm -
Nonstop2h 05m
Sat 11/146:15 pm -
Nonstop1h 59m
Deal found 10/26![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 10/26. 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.
Sun 11/224:37 pm -
1 stop7h 17m
Thu 11/264:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$343
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/1112:34 pm -
1 stop6h 04m
Tue 11/175:19 am -
1 stop5h 40m
Deal found 10/26![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 10/27. 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 11/246:00 am -
2 stops8h 59m
Thu 12/38:04 am -
1 stop4h 48m
Deal found 10/27![Delta logo]()
$349
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 October 30, 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 October 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/25. 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 12/45:22 am -
Nonstop2h 03m
Tue 12/89:05 pm -
Nonstop1h 45m
Deal found 10/25![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 10/25. 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 12/46:59 pm -
1 stop4h 55m
Tue 12/811:28 am -
1 stop5h 51m
Deal found 10/25![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/241:50 pm -
Nonstop2h 05m
Sat 11/2810:25 am -
Nonstop1h 48m
Deal found 10/29![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 10/29. 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 3/246:40 pm -
1 stop4h 40m
Tue 3/309:30 am -
1 stop4h 11m
Deal found 10/29![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/25. 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 12/42:32 pm -
1 stop5h 37m
Tue 12/86:16 pm -
1 stop4h 24m
Deal found 10/25![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/26. 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.
Sun 11/224:37 pm -
1 stop7h 17m
Thu 11/264:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 10/25. 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 11/246:00 am -
2 stops8h 59m
Thu 12/38:04 am -
1 stop4h 48m
Deal found 10/25![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 10/28. 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 11/126:58 pm -
1 stop4h 56m
Mon 11/165:13 pm -
1 stop5h 30m
Deal found 10/28![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 10/29. 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 11/136:00 am -
1 stop5h 25m
Sun 11/155:30 am -
1 stop4h 10m
Deal found 10/29![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:45 pm -
1 stop7h 09m
Wed 11/181:31 pm -
2 stops9h 12m
Deal found 10/30![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 10/25. 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 11/244:37 pm -
1 stop7h 17m
Thu 12/35:12 pm -
1 stop5h 28m
Deal found 10/25![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 10/28. 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 11/236:00 am -
2 stops8h 59m
Tue 11/248:04 am -
1 stop6h 47m
Deal found 10/28![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/26. 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 11/236:00 am -
1 stop5h 24m
Fri 11/274:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 10/26. 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 11/246:00 am -
2 stops7h 51m
Fri 11/274:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$414
Last-minute flights from Charleston to ChicagoDiscover last-minute flight deals from Charleston to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Chicago. Data last updated October 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/47:08 pm -
1 stop5h 53m
Tue 11/174:40 pm -
1 stop5h 21m
Deal found 10/26![American Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 10/26. 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 11/46:00 am -
2 stops7h 59m
Tue 11/178:04 am -
1 stop4h 49m
Deal found 10/26![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/26. 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 11/411:11 am -
2 stops7h 49m
Tue 11/1710:34 am -
2 stops12h 09m
Deal found 10/26![Delta logo]()
$384
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/41:50 pm -
Nonstop2h 05m
Tue 11/1710:25 am -
Nonstop1h 50m
Deal found 10/26![United Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/66:02 am -
Nonstop2h 03m
Sat 11/710:25 am -
Nonstop1h 48m
Deal found 10/28![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 10/26. 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 11/116:00 am -
2 stops7h 51m
Tue 11/1712:30 pm -
2 stops10h 13m
Deal found 10/26![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/28. 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 11/126:58 pm -
1 stop4h 56m
Mon 11/165:13 pm -
1 stop5h 30m
Deal found 10/28![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
2 stops11h 39m
Wed 11/181:31 pm -
2 stops9h 12m
Deal found 10/30![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 10/26. 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 11/214:48 pm -
1 stop7h 06m
Thu 11/264:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 10/26. 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.
Sun 11/224:37 pm -
1 stop7h 17m
Thu 11/264:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 10/26. 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 11/236:00 am -
2 stops7h 51m
Fri 11/274:13 pm -
1 stop5h 06m
Deal found 10/26![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/27. 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 11/244:37 pm -
1 stop7h 17m
Thu 12/36:00 am -
1 stop6h 52m
Deal found 10/27![Delta logo]()
$373
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 October 30, 2026.
Search for one-way flight options from Charleston to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/2211:50 am -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$208
This United Airlines deal was found by Cheapflights users on 10/26. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 10/26. 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.
Sun 11/224:37 pm -
1 stop7h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$283
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/68:00 pm -
1 stop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/96:02 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 10/26. 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 11/911:20 am -
2 stops9h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/61:50 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 10/29. 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 11/64:35 pm -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 10/26. 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.
Sun 11/226:00 am -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 10/27. 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 11/611:11 am -
2 stops10h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$660
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $260 (American Airlines) |
One-way from | $208 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $473 |
Good round-trip deal | $393 or less |
Good one-way deal | $326 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 7,457,451 searches. Data last updated October 30, 2026.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Sun 11/22
11:50 am-5:44 pm
1 stop6h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$208
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Sun 11/22
1:50 pm-2:55 pm
Nonstop2h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$222
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 11/6
8:00 pm-11:40 pm
1 stop4h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$293
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 12/4
5:22 am-6:25 am
Nonstop2h 03m
Chicago O'Hare Intl
Tue 12/8
9:05 pm-11:50 pm
Nonstop1h 45m
$309
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Tue 11/24
1:50 pm-2:55 pm
Nonstop2h 05m
Chicago O'Hare Intl
Sat 11/28
10:25 am-1:13 pm
Nonstop1h 48m
$324
CharlestonChicago
CRW Charleston Yeager - MDW Chicago Midway
CRWMDW
Charleston Yeager
Fri 12/4
6:59 pm-10:54 pm
1 stop4h 55m
Chicago Midway
Tue 12/8
11:28 am-6:19 pm
1 stop5h 51m
$328
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Wed 3/24
6:40 pm-10:20 pm
1 stop4h 40m
Chicago O'Hare Intl
Tue 3/30
9:30 am-2:41 pm
1 stop4h 11m
$328
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 12/4
2:32 pm-7:09 pm
1 stop5h 37m
Chicago O'Hare Intl
Tue 12/8
6:16 pm-11:40 pm
1 stop4h 24m
$328
Quickest round-trip
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Mon 11/9
6:02 am-7:05 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$334
CharlestonChicago
CRW Charleston Yeager - MDW Chicago Midway
CRWMDW
Charleston Yeager
Sun 11/22
4:37 pm-10:54 pm
1 stop7h 17m
Chicago Midway
Thu 11/26
4:13 pm-10:19 pm
1 stop5h 06m
$343
Showing 1-10 of 24 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
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
What is the cheapest month to book a flight from Charleston, West Virginia to Chicago?
Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $271). Flying from Charleston, West Virginia to Chicago in October is currently the most expensive (average of $473). 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 October 30, 2026.
It’s optimal to fly from Charleston, West Virginia to Chicago in the evening. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight at noon.
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 October 24, 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 October 30, 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.
Comfort
7.3
Crew
8.1
Food
6.7
Overall
7.3
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Crew
8.1
Food
6.7
Overall
7.3
Boarding
7.7
Entertainment
7.1
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Charleston and Chicago flights
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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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$194 | Average$341 | FlexibilityNo cancel fee | On-time69% |