$178+ Cheap flights from Charleston, WV (CRW) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — CHI
Sep 27 — Oct 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 28, 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 28, 2026.
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/177:00 am -
Nonstop1h 57m
Fri 9/256:51 am -
Nonstop1h 52m
Deal found 8/25![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 12/511:13 am -
1 stop4h 52m
Mon 12/75:14 pm -
1 stop5h 26m
Deal found 8/24![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 8/25. 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 11/132:35 pm -
1 stop5h 30m
Sun 11/156:49 am -
1 stop6h 06m
Deal found 8/25![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 10/166:05 pm -
Nonstop1h 58m
Sun 10/186:51 am -
Nonstop1h 52m
Deal found 8/26![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 12/511:13 am -
2 stops10h 02m
Mon 12/78:39 am -
2 stops8h 40m
Deal found 8/24![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/24:24 pm -
1 stop7h 07m
Fri 10/164:45 pm -
1 stop6h 14m
Deal found 8/24![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Thu 9/2412:45 pm -
1 stop5h 53m
Sun 9/275:18 am -
1 stop4h 07m
Deal found 8/26![American Airlines logo]()
$288
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/26:05 pm -
Nonstop1h 58m
Fri 10/169:20 pm -
Nonstop1h 39m
Deal found 8/24![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 9/236:54 pm -
1 stop4h 50m
Mon 10/261:27 pm -
2 stops9h 03m
Deal found 8/27![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 9/236:54 pm -
1 stop6h 05m
Mon 10/261:45 pm -
2 stops8h 45m
Deal found 8/27![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:24 pm -
1 stop7h 07m
Sun 9/135:18 am -
1 stop4h 07m
Deal found 8/25![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Fri 9/116:05 pm -
Nonstop1h 57m
Tue 9/156:51 am -
Nonstop1h 52m
Deal found 8/27![United Airlines logo]()
$299
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 28, 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 28, 2026.
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 12/511:13 am -
1 stop4h 52m
Mon 12/75:14 pm -
1 stop5h 26m
Deal found 8/23![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 9/186:05 pm -
Nonstop1h 57m
Sun 9/206:30 am -
Nonstop1h 52m
Deal found 8/26![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 -
2 stops8h 59m
Sun 11/156:49 am -
1 stop6h 06m
Deal found 8/24![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/232:38 pm -
2 stops7h 49m
Sun 10/256:30 am -
1 stop6h 28m
Deal found 8/23![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/216:00 am -
2 stops7h 59m
Sun 10/256:30 am -
1 stop6h 28m
Deal found 8/23![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/46:05 pm -
Nonstop1h 58m
Mon 10/129:20 pm -
Nonstop1h 39m
Deal found 8/22![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Sat 9/510:45 am -
Nonstop2h 00m
Mon 9/79:10 pm -
Nonstop1h 49m
Deal found 8/25![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 stops7h 59m
Mon 10/263:40 pm -
1 stop6h 50m
Deal found 8/24![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 11/131:50 pm -
Nonstop2h 05m
Sun 11/1510:25 am -
Nonstop1h 50m
Deal found 8/23![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 8/26. 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.
Fri 9/46:50 pm -
1 stop6h 07m
Sun 9/66:59 am -
2 stops7h 55m
Deal found 8/26![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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
Mon 10/265:09 pm -
1 stop5h 21m
Deal found 8/24![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 8/26. 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.
Fri 9/186:54 pm -
1 stop4h 50m
Sun 9/205:10 pm -
1 stop5h 10m
Deal found 8/26![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 8/25. 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.
Wed 9/94:45 pm -
1 stop6h 59m
Sun 9/1310:48 am -
1 stop4h 04m
Deal found 8/25![Delta logo]()
$688
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/236:00 am -
2 stops7h 39m
Thu 9/246:05 am -
1 stop6h 48m
Deal found 8/23![Delta logo]()
$718
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/711:07 am -
2 stops8h 26m
Fri 9/119:29 am -
2 stops11h 23m
Deal found 8/23![Delta logo]()
$803
This Delta deal was found by Cheapflights users on 8/27. 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 10/306:00 am -
2 stops7h 47m
Sun 11/11:27 pm -
2 stops7h 40m
Deal found 8/27![Delta logo]()
$869
This Delta deal was found by Cheapflights users on 8/25. 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.
Mon 10/196:58 pm -
1 stop4h 35m
Fri 10/231:27 pm -
2 stops9h 03m
Deal found 8/25![Delta logo]()
$948
Last-minute flights from Charleston to ChicagoDiscover last-minute flight deals from Charleston to Chicago. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Chicago. Data last updated August 28, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Wed 9/26:05 pm -
Nonstop2h 00m
Fri 9/116:30 am -
Nonstop1h 52m
Deal found 8/27![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 9/26:00 am -
1 stop4h 59m
Fri 9/114:30 pm -
1 stop4h 22m
Deal found 8/27![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 9/211:07 am -
1 stop6h 44m
Fri 9/111:51 pm -
1 stop7h 01m
Deal found 8/27![Delta logo]()
$403
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/310:25 am -
1 stop4h 57m
Sun 9/67:30 am -
1 stop6h 30m
Deal found 8/24![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/36:50 pm -
1 stop6h 07m
Sun 9/66:00 am -
2 stops8h 54m
Deal found 8/24![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/46:50 pm -
1 stop6h 07m
Sun 9/66:59 am -
2 stops7h 55m
Deal found 8/23![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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
Sun 9/67:00 am -
Nonstop1h 54m
Deal found 8/23![United Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/46:55 pm -
1 stop6h 04m
Sun 9/68:54 am -
1 stop5h 06m
Deal found 8/23![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/79:10 pm -
Nonstop1h 49m
Deal found 8/24![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 8/26. 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.
Fri 9/186:54 pm -
1 stop4h 50m
Sun 9/205:10 pm -
1 stop5h 10m
Deal found 8/26![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 8/27. 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.
Wed 9/236:54 pm -
1 stop4h 50m
Mon 10/261:27 pm -
2 stops9h 03m
Deal found 8/27![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/236:54 pm -
1 stop4h 50m
Thu 9/246:05 am -
1 stop6h 48m
Deal found 8/23![Delta logo]()
$506
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 28, 2026.
Search for one-way flight options from Charleston to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/184:24 pm -
1 stop7h 07m
Deal found 8/23![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Mon 10/197:59 pm -
1 stop5h 09m
Deal found 8/27![American Airlines logo]()
$188
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 9/114:24 pm -
1 stop7h 07m
Deal found 8/26![American Airlines logo]()
$228
This KAYAK deal was found by Cheapflights users on 8/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:37 pm -
1 stop4h 59m
Deal found 8/27![American Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/186:54 pm -
1 stop4h 50m
Deal found 8/23![Delta logo]()
$253
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Mon 10/196:05 pm -
Nonstop1h 58m
Deal found 8/27![United Airlines logo]()
$254
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Sun 9/1310:00 am -
Nonstop2h 00m
Deal found 8/27![United Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:59 am -
2 stops26h 51m
Deal found 8/26![Multiple Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Mon 8/3110:25 am -
1 stop6h 35m
Deal found 8/26![American Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 9/117:00 am -
Nonstop1h 57m
Deal found 8/26![United Airlines logo]()
$334
This KAYAK deal was found by Cheapflights users on 8/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am -
2 stops15h 31m
Deal found 8/27![Delta logo]()
$488
This United Airlines deal was found by Cheapflights users on 8/26. 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 8/3110:45 am -
Nonstop2h 00m
Deal found 8/26![United Airlines logo]()
$499
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 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (United Airlines) |
One-way from | $178 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $393 |
Good round-trip deal | $332 or less |
Good one-way deal | $308 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 August 28, 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 - MDW Chicago Midway
CRWMDW
Charleston Yeager
Sat 12/5
11:13 am-3:05 pm
1 stop4h 52m
Chicago Midway
Mon 12/7
5:14 pm-11:40 pm
1 stop5h 26m
$268
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 11/13
6:00 am-1:59 pm
2 stops8h 59m
Chicago O'Hare Intl
Sun 11/15
6:49 am-1:55 pm
1 stop6h 06m
$274
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 10/23
2:38 pm-9:27 pm
2 stops7h 49m
Chicago O'Hare Intl
Sun 10/25
6:30 am-1:58 pm
1 stop6h 28m
$319
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Wed 10/21
6:00 am-12:59 pm
2 stops7h 59m
Chicago O'Hare Intl
Sun 10/25
6:30 am-1:58 pm
1 stop6h 28m
$334
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 9/18
6:05 pm-7:02 pm
Nonstop1h 57m
Chicago O'Hare Intl
Sun 9/20
6:30 am-9:22 am
Nonstop1h 52m
$339
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Sat 10/17
6:00 am-12:59 pm
2 stops7h 59m
Chicago O'Hare Intl
Mon 10/26
3:40 pm-11:30 pm
1 stop6h 50m
$354
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 9/4
6:50 pm-11:57 pm
1 stop6h 07m
Chicago O'Hare Intl
Sun 9/6
6:59 am-3:54 pm
2 stops7h 55m
$384
Quickest round-trip
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Sun 10/4
6:05 pm-7:03 pm
Nonstop1h 58m
Chicago O'Hare Intl
Mon 10/12
9:20 pm-11:59 pm
Nonstop1h 39m
$409
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Sat 9/5
10:45 am-11:45 am
Nonstop2h 00m
Chicago O'Hare Intl
Mon 9/7
9:10 pm-11:59 pm
Nonstop1h 49m
$409
CharlestonChicago
CRW Charleston Yeager - ORD Chicago O'Hare Intl
CRWORD
Charleston Yeager
Fri 11/13
1:50 pm-2:55 pm
Nonstop2h 05m
Chicago O'Hare Intl
Sun 11/15
10:25 am-1:15 pm
Nonstop1h 50m
$419
Showing 1-10 of 31 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
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, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Chicago (average of $263). 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 28, 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 28, 2026.
The most flights from CRW to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Charleston, West Virginia to Chicago?
Airfare is typical for this route at the moment.
Charleston, West Virginia to Chicago flights typically cost between $239 and $308 in September.The cheapest round-trip price found within the last 5 days was $249 on United Airlines (Sep 17-Sep 25).
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 22, 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 28, 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
Comfort
7.3
Overall
7.4
Boarding
7.7
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Food
6.7
Crew
8.1
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Charleston
Popular flights
Alternative routes for Charleston to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Charleston to Chicago by cabin class
Find flights from Charleston to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Charleston and Chicago flights
Browse other Charleston and Chicago flight options. Last updated on August 28, 2026.
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 28, 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 7,457,451 searches. Data last updated August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$304 | FlexibilityNo cancel fee | On-time69% |