$108+ Cheap flights from Charleston (CHS) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
Oct 21 — Oct 281
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.Cheapflights Tip: The best prices from Charleston to Chicago are usually found in January or September, booked 52 days in advance, depart on a Friday or Thursday and return on a Tuesday
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 September 21, 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 September 21, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:53 pm -
1 stop4h 39m
Wed 10/216:10 pm -
Nonstop2h 23m
Deal found 9/17![United Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:00 pm -
2 stops28h 16m
Thu 10/298:00 am -
1 stop7h 11m
Deal found 9/18![Multiple Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:16 am -
Nonstop2h 43m
Wed 10/78:40 pm -
Nonstop2h 19m
Deal found 9/17![American Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/310:15 pm -
1 stop16h 41m
Mon 12/76:10 am -
1 stop13h 51m
Deal found 9/19![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:52 pm -
1 stop14h 48m
Mon 11/1610:38 am -
1 stop21h 00m
Deal found 9/19![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
2 stops34h 30m
Mon 10/268:04 am -
1 stop11h 57m
Deal found 9/20![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/194:57 pm -
1 stop23h 33m
Mon 10/268:04 am -
1 stop11h 57m
Deal found 9/21![Multiple Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:10 am -
1 stop6h 37m
Mon 10/195:09 pm -
1 stop5h 50m
Deal found 9/17![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:10 am -
1 stop6h 49m
Mon 10/191:25 pm -
1 stop7h 40m
Deal found 9/17![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:15 pm -
Nonstop2h 10m
Mon 10/198:35 am -
1 stop6h 35m
Deal found 9/16![Southwest logo]()
$296
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:16 am -
Nonstop2h 43m
Tue 10/138:40 pm -
Nonstop2h 19m
Deal found 9/17![American Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:15 am -
2 stops9h 35m
Mon 10/198:35 am -
1 stop6h 35m
Deal found 9/17![Southwest logo]()
$305
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 September 21, 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 September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:52 pm -
1 stop14h 48m
Mon 11/1610:38 am -
1 stop21h 00m
Deal found 9/19![Multiple Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:30 am -
Nonstop2h 30m
Mon 10/197:00 am -
Nonstop2h 27m
Deal found 9/16![United Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:15 am -
2 stops9h 35m
Mon 10/198:35 am -
1 stop6h 35m
Deal found 9/17![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/307:10 am -
1 stop6h 37m
Sat 10/316:04 am -
1 stop4h 00m
Deal found 9/20![Delta logo]()
$353
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:15 am -
Nonstop2h 10m
Thu 10/2912:55 pm -
Nonstop2h 10m
Deal found 9/18![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/108:00 am -
Nonstop2h 32m
Sat 10/176:18 pm -
Nonstop2h 23m
Deal found 9/19![United Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/196:30 am -
Nonstop2h 30m
Mon 10/2610:40 am -
Nonstop2h 16m
Deal found 9/18![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/167:05 pm -
1 stop5h 52m
Mon 10/191:25 pm -
1 stop7h 40m
Deal found 9/19![Delta logo]()
$353
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:15 pm -
Nonstop2h 10m
Mon 10/1912:55 pm -
Nonstop2h 10m
Deal found 9/16![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/1711:28 am -
Nonstop2h 32m
Sat 10/246:18 pm -
Nonstop2h 23m
Deal found 9/19![United Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/42:13 pm -
1 stop20h 41m
Wed 10/79:34 am -
1 stop22h 04m
Deal found 9/16![Multiple Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:30 am -
Nonstop2h 10m
Sat 10/2410:25 am -
2 stops7h 20m
Deal found 9/19![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:01 pm -
1 stop5h 51m
Sun 12/1311:35 am -
1 stop5h 21m
Deal found 9/17![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:53 pm -
1 stop4h 39m
Sun 10/257:45 am -
Nonstop2h 34m
Deal found 9/17![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/295:30 am -
1 stop4h 55m
Sun 11/15:27 am -
1 stop4h 40m
Deal found 9/21![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:00 am -
2 stops6h 45m
Fri 11/612:45 pm -
Nonstop2h 05m
Deal found 9/19![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/287:19 pm -
Nonstop2h 41m
Fri 10/302:30 pm -
Nonstop2h 34m
Deal found 9/18![United Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:13 pm -
1 stop18h 41m
Mon 10/2610:44 am -
2 stops11h 58m
Deal found 9/17![Multiple Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:10 am -
2 stops8h 20m
Fri 10/3012:45 pm -
2 stops8h 00m
Deal found 9/18![Southwest logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:13 pm -
1 stop18h 46m
Sun 10/410:08 am -
2 stops26h 42m
Deal found 9/18![Multiple Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:35 pm -
1 stop5h 05m
Sun 11/812:45 pm -
Nonstop2h 05m
Deal found 9/21![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:29 pm -
Nonstop2h 36m
Mon 11/237:47 am -
Nonstop2h 34m
Deal found 9/17![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:10 pm -
Nonstop2h 15m
Sun 11/812:45 pm -
Nonstop2h 05m
Deal found 9/19![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:39 pm -
1 stop12h 47m
Sun 12/69:45 am -
2 stops11h 25m
Deal found 9/17![Multiple Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:45 pm -
1 stop4h 10m
Sun 11/18:45 am -
2 stops8h 45m
Deal found 9/21![Southwest logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop6h 48m
Fri 10/164:00 pm -
1 stop7h 15m
Deal found 9/18![United Airlines logo]()
$453
Last-minute flights from Charleston to ChicagoDiscover last-minute flight deals from Charleston to Chicago. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Chicago. Data last updated September 21, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:58 pm -
Nonstop2h 32m
Sat 10/106:06 pm -
1 stop5h 09m
Deal found 9/16![United Airlines logo]()
$243
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:16 am -
Nonstop2h 43m
Sat 10/1011:45 am -
Nonstop2h 17m
Deal found 9/16![American Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:18 am -
1 stop14h 41m
Sat 10/107:44 pm -
2 stops25h 52m
Deal found 9/16![Multiple Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:02 am -
1 stop7h 03m
Wed 10/78:40 pm -
Nonstop2h 19m
Deal found 9/17![American Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:50 pm -
Nonstop2h 39m
Tue 10/137:00 am -
Nonstop2h 27m
Deal found 9/16![United Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:53 pm -
1 stop4h 39m
Wed 10/216:06 pm -
1 stop5h 09m
Deal found 9/17![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:15 pm -
Nonstop2h 10m
Mon 10/198:35 am -
1 stop6h 35m
Deal found 9/16![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:10 am -
1 stop6h 37m
Mon 10/195:09 pm -
1 stop5h 50m
Deal found 9/17![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:10 am -
1 stop6h 49m
Mon 10/191:25 pm -
1 stop7h 40m
Deal found 9/17![Delta logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/194:57 pm -
1 stop23h 33m
Mon 10/268:04 am -
1 stop11h 57m
Deal found 9/21![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
2 stops34h 30m
Mon 10/268:04 am -
1 stop11h 57m
Deal found 9/20![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:00 pm -
2 stops28h 16m
Thu 10/298:00 am -
1 stop7h 11m
Deal found 9/18![Multiple Airlines logo]()
$270
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 September 21, 2026.
Search for one-way flight options from Charleston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/168:09 pm -
1 stop17h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:21 pm -
2 stops26h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$114
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:00 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$117
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:00 am -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
2 stops34h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$126
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:30 am -
1 stop5h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$127
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:10 am -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:21 pm -
2 stops27h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$128
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:55 pm -
2 stops9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/131:21 pm -
2 stops27h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:00 pm -
1 stop19h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:16 am -
Nonstop2h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$136
Find flight deals from Charleston to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CHS) 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 September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (United Airlines) |
One-way from | $108 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $329 |
Good round-trip deal | $382 or less |
Good one-way deal | $195 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 September 21, 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
CHS Charleston - ORD Chicago O'Hare Intl
CHSORD
Charleston
Sat 10/10
6:50 pm-11:30 pm
1 stop5h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
CharlestonChicago
CHS Charleston - ORD Chicago O'Hare Intl
CHSORD
Charleston
Tue 10/20
4:58 pm-6:30 pm
Nonstop2h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Wed 12/16
5:15 pm-9:25 pm
1 stop5h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$127
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Tue 10/13
5:30 am-10:03 am
1 stop5h 33m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$127
CharlestonChicago
CHS Charleston - ORD Chicago O'Hare Intl
CHSORD
Charleston
Tue 10/6
7:10 am-12:59 pm
1 stop6h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$127
CharlestonChicago
CHS Charleston - ORD Chicago O'Hare Intl
CHSORD
Charleston
Sat 10/10
7:53 pm-11:31 pm
1 stop4h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$127
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Mon 11/16
7:04 pm-10:54 pm
1 stop4h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Quickest round-trip
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Fri 10/16
7:15 pm-8:25 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$152
CharlestonChicago
CHS Charleston - ORD Chicago O'Hare Intl
CHSORD
Charleston
Thu 10/15
6:50 pm-11:30 pm
1 stop5h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
CharlestonChicago
CHS Charleston - MDW Chicago Midway
CHSMDW
Charleston
Wed 11/18
8:00 am-9:15 am
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Showing 1-10 of 53 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Charleston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charleston-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charleston-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Charleston-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-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.
CHS-CHI
CHS-ORD
CHS-MDW
CHS-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Charleston to Chicago
CHS-CHI
CHS-ORD
CHS-MDW
CHS-RFD
What is the cheapest month to book a flight from Charleston to Chicago?
Currently, September is the cheapest month in which you can book a flight from Charleston to Chicago (average of $342). Flying from Charleston to Chicago in July is currently the most expensive (average of $412). 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 CHS 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 September 21, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 33% on flights from Charleston to Chicago by exploring options for tickets in the evening.
Weekly flight availability from Charleston 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 September 21, 2026.
The most flights from CHS to CHI are scheduled on a Monday (22 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Charleston to Chicago?
Airfare is below average for this route at the moment.
Charleston to Chicago flights typically cost between $272 and $460 in October.The cheapest round-trip price found within the last 5 days was $243 on United Airlines (Oct 6-Oct 10).
How far ahead should I book a flight from Charleston to Chicago?
The price you pay for your flight from Charleston to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 51 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Charleston to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Charleston to Chicago. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Charleston to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Charleston to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Charleston to Chicago trip
Our travel experts
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 September 21, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Charleston to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Charleston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Complete your trip
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Charleston and Chicago flights
Browse other Charleston and Chicago flight options. Last updated on September 21, 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 September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Charleston to Chicago
Discover the top 3 airlines 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 September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$257 | Average$375 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$323 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$275 | Average$393 | FlexibilityNo cancel fee | On-time69% |