$198+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Nov 11 — Nov 181
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from 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 12, 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 12, 2026.
This United Airlines deal was found by Cheapflights users on 10/11. 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 11/76:02 am -
Nonstop2h 03m
Wed 11/1110:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Wed 10/286:02 am -
Nonstop2h 03m
Wed 11/2510:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 10/8. 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.
Fri 11/132:35 pm -
1 stop7h 14m
Sun 11/155:30 am -
1 stop4h 10m
Deal found 10/8![Delta logo]()
$308
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Fri 10/237:03 am -
Nonstop1h 57m
Tue 10/2710:25 am -
Nonstop1h 50m
Deal found 10/8![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:59 pm -
1 stop5h 09m
Sun 10/255:00 am -
1 stop4h 29m
Deal found 10/8![American Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:58 pm -
1 stop4h 35m
Sat 10/311:27 pm -
2 stops6h 45m
Deal found 10/12![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 10/244:35 pm -
1 stop5h 03m
Wed 10/281:55 pm -
2 stops8h 35m
Deal found 10/8![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Fri 11/66:02 am -
Nonstop2h 03m
Wed 11/1110:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 10/11. 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 10/174:35 pm -
1 stop6h 58m
Sat 10/244:19 pm -
1 stop4h 58m
Deal found 10/11![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 10/176:00 am -
2 stops9h 36m
Sat 10/243:15 pm -
1 stop6h 02m
Deal found 10/8![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 10/226:00 am -
2 stops7h 47m
Sun 10/251:27 pm -
2 stops9h 03m
Deal found 10/11![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/10. 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.
Fri 10/2311:11 am -
2 stops8h 18m
Sun 10/251:55 pm -
2 stops8h 35m
Deal found 10/10![Delta logo]()
$379
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 12, 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 12, 2026.
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Wed 10/286:02 am -
Nonstop2h 03m
Wed 11/2510:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 11/132:35 pm -
1 stop5h 30m
Sun 11/156:49 am -
1 stop6h 04m
Deal found 10/9![Delta logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:43 pm -
1 stop29h 19m
Wed 12/308:07 pm -
1 stop12h 12m
Deal found 10/9![Multiple Airlines logo]()
$567
This Delta deal was found by Cheapflights users on 10/10. 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.
Wed 3/2411:00 am -
1 stop6h 37m
Tue 3/307:10 am -
1 stop6h 31m
Deal found 10/10![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 10/11. 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.
Fri 3/1911:00 am -
2 stops8h 40m
Mon 3/221:35 pm -
2 stops8h 04m
Deal found 10/11![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:58 pm -
1 stop4h 35m
Sat 10/311:27 pm -
2 stops6h 45m
Deal found 10/12![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 10/226:00 am -
1 stop5h 03m
Sun 10/251:27 pm -
2 stops9h 03m
Deal found 10/11![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/10. 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.
Fri 10/2311:11 am -
2 stops8h 18m
Sun 10/251:55 pm -
2 stops8h 35m
Deal found 10/10![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/8. 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.
Fri 10/236:00 am -
1 stop6h 54m
Tue 10/2710:59 am -
1 stop6h 19m
Deal found 10/8![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:59 pm -
1 stop4h 55m
Sun 1/35:05 pm -
1 stop4h 09m
Deal found 10/7![Delta logo]()
$667
This Delta deal was found by Cheapflights users on 10/10. 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.
Sun 10/256:58 pm -
1 stop4h 35m
Thu 10/2910:12 am -
2 stops12h 18m
Deal found 10/10![Delta logo]()
$672
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:58 pm -
1 stop4h 56m
Sun 11/156:00 am -
1 stop6h 53m
Deal found 10/10![Delta logo]()
$683
This Delta deal was found by Cheapflights users on 10/11. 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 11/244:37 pm -
1 stop7h 17m
Sat 11/286:00 am -
1 stop6h 53m
Deal found 10/11![Delta logo]()
$768
Last-minute flights from Charleston to ChicagoDiscover last-minute flight deals from Charleston to Chicago. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Chicago. Data last updated October 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/11. 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 10/174:35 pm -
1 stop6h 58m
Sat 10/244:19 pm -
1 stop4h 58m
Deal found 10/11![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 10/176:00 am -
2 stops9h 36m
Sat 10/243:15 pm -
1 stop6h 02m
Deal found 10/8![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 10/226:00 am -
2 stops7h 47m
Sun 10/251:27 pm -
2 stops9h 03m
Deal found 10/11![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Fri 10/237:03 am -
Nonstop1h 57m
Tue 10/2710:25 am -
Nonstop1h 50m
Deal found 10/8![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:59 pm -
1 stop5h 09m
Tue 10/274:45 pm -
1 stop5h 13m
Deal found 10/8![American Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 10/10. 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 10/237:59 pm -
1 stop5h 09m
Sun 10/255:00 am -
1 stop4h 29m
Deal found 10/10![American Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 10/244:35 pm -
1 stop5h 03m
Wed 10/281:55 pm -
2 stops8h 35m
Deal found 10/8![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:58 pm -
1 stop4h 35m
Sat 10/311:27 pm -
2 stops6h 45m
Deal found 10/12![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Wed 10/286:02 am -
Nonstop2h 03m
Wed 11/2510:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Fri 11/66:02 am -
Nonstop2h 03m
Wed 11/1110:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 10/11. 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 11/76:02 am -
Nonstop2h 03m
Wed 11/1110:25 am -
Nonstop1h 50m
Deal found 10/11![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 10/8. 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.
Fri 11/132:35 pm -
1 stop7h 14m
Sun 11/155:30 am -
1 stop4h 10m
Deal found 10/8![Delta logo]()
$308
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 12, 2026.
Search for one-way flight options from Charleston to Chicago. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:08 pm -
1 stop5h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$198
This deal was found by Cheapflights users on 10/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:02 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![United Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:54 pm -
1 stop5h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:59 am -
2 stops24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:59 am -
2 stops32h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Mon 11/21:50 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![United Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 10/3011:11 am -
1 stop6h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 10/302:38 pm -
2 stops7h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Fri 10/306:02 am -
Nonstop2h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 10/9. 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.
Mon 11/211:11 am -
2 stops10h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:43 pm -
2 stops34h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 10/11. 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 1/236:00 am -
1 stop7h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$338
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (United Airlines) |
One-way from | $198 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $473 |
Good round-trip deal | $433 or less |
Good one-way deal | $343 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 12, 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
Thu 10/29
11:00 am-4:05 pm
1 stop6h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$205
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Tue 11/10
6:02 am-7:05 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$241
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Thu 10/29
6:02 am-7:05 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$245
CharlestonChicago
CRW Charleston Yeager - MDW Chicago Midway
CRWMDW
Charleston Yeager
Fri 10/30
11:11 am-4:14 pm
1 stop6h 03m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$273
CharlestonChicago
CRW Charleston Yeager - MDW Chicago Midway
CRWMDW
Charleston Yeager
Wed 11/4
4:35 pm-10:33 pm
1 stop6h 58m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$273
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Wed 10/28
6:02 am-7:05 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 11/25
10:25 am-1:15 pm
Nonstop1h 50m
$304
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 11/13
2:35 pm-7:05 pm
1 stop5h 30m
Chicago O'Hare Intl
Sun 11/15
6:49 am-1:53 pm
1 stop6h 04m
$308
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Wed 3/24
11:00 am-4:37 pm
1 stop6h 37m
Chicago O'Hare Intl
Tue 3/30
7:10 am-2:41 pm
1 stop6h 31m
$308
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Thu 11/5
6:02 am-7:05 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Wed 11/4
6:02 am-7:05 am
Nonstop2h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Showing 1-10 of 29 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 |
- 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 12, 2026.
It’s optimal to fly from Charleston, West Virginia to Chicago in the afternoon. By choosing this option you can save up to 20% 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 October 12, 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 $334 and $534 in November.The cheapest round-trip price found within the last 5 days was $289 on United Airlines (Nov 7-Nov 12).
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 10, 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 12, 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
Overall
7.4
Entertainment
7.1
Crew
8.1
Food
6.7
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Overall
7.4
Entertainment
7.1
Crew
8.1
Food
6.7
Boarding
7.7
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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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 October 12, 2026.
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Charleston and Chicago flights
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Other flights from Charleston
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Popular flight searches
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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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$194 | Average$340 | FlexibilityNo cancel fee | On-time69% |