$84+ Cheap flights from Greenville (GSP) 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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Find cheap flights from Greenville 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 Greenville to Chicago are usually found in February or November, booked 61 days in advance, depart on a Thursday or Saturday and return on a Saturday
Cheap flight deals from Greenville to Chicago
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Cheapest flights from Greenville to ChicagoExplore the most affordable flight options available from Greenville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
Explore the most affordable flight options available from Greenville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Fri 10/168:32 pm -
1 stop17h 44m
Mon 10/197:45 am -
2 stops9h 38m
Deal found 8/9![Multiple Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am -
1 stop4h 50m
Fri 9/43:20 pm -
1 stop5h 15m
Deal found 8/11![Southwest logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 8/238:37 am -
1 stop29h 13m
Wed 8/268:05 am -
1 stop22h 52m
Deal found 8/9![Multiple Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:40 pm -
2 stops6h 40m
Mon 8/318:00 am -
1 stop3h 30m
Deal found 8/10![Southwest logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Sat 9/268:24 pm -
2 stops19h 21m
Tue 9/297:11 am -
1 stop9h 03m
Deal found 8/9![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:24 pm -
2 stops19h 21m
Fri 10/27:11 am -
1 stop10h 19m
Deal found 8/10![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:40 pm -
1 stop5h 20m
Sun 9/68:55 am -
1 stop3h 45m
Deal found 8/10![Southwest logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:32 pm -
1 stop27h 27m
Thu 9/173:50 pm -
1 stop15h 55m
Deal found 8/11![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:08 pm -
1 stop22h 18m
Sun 10/259:33 pm -
2 stops17h 14m
Deal found 8/7![Multiple Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:18 pm -
Nonstop2h 12m
Sun 9/610:25 am -
Nonstop2h 07m
Deal found 8/10![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:40 am -
2 stops7h 50m
Tue 9/226:30 am -
2 stops9h 15m
Deal found 8/10![Southwest logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:38 pm -
1 stop25h 07m
Sun 10/47:28 pm -
2 stops21h 55m
Deal found 8/7![Multiple Airlines logo]()
$282
Best flights from Greenville to ChicagoDiscover carefully curated flight deals from Greenville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
Discover carefully curated flight deals from Greenville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
This United Airlines deal was found by Cheapflights users on 8/11. 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.
Thu 9/106:20 am -
Nonstop2h 07m
Mon 9/146:15 pm -
Nonstop2h 03m
Deal found 8/11![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/10. 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 10/2910:08 am -
1 stop5h 20m
Sat 10/3110:55 am -
1 stop5h 45m
Deal found 8/10![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:20 pm -
1 stop6h 25m
Mon 9/283:20 pm -
1 stop5h 20m
Deal found 8/7![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:46 pm -
Nonstop2h 19m
Sun 10/256:29 am -
Nonstop2h 01m
Deal found 8/10![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/9. 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.
Wed 9/3011:04 am -
1 stop6h 09m
Sat 10/37:05 am -
1 stop3h 54m
Deal found 8/9![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:20 pm -
1 stop3h 50m
Sat 10/176:45 am -
1 stop4h 25m
Deal found 8/8![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:43 pm -
Nonstop2h 20m
Mon 8/315:59 pm -
Nonstop2h 08m
Deal found 8/10![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/9. 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.
Wed 9/26:00 am -
1 stop4h 23m
Tue 9/86:40 am -
1 stop5h 10m
Deal found 8/9![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:55 pm -
1 stop4h 25m
Sun 8/307:35 am -
1 stop4h 05m
Deal found 8/7![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:43 pm -
Nonstop2h 20m
Sat 8/291:55 pm -
Nonstop2h 07m
Deal found 8/7![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/11. 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 9/267:15 am -
1 stop4h 22m
Tue 9/296:40 am -
1 stop5h 10m
Deal found 8/11![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:25 pm -
1 stop7h 00m
Wed 10/141:40 pm -
2 stops5h 20m
Deal found 8/8![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 8/11. 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 11/512:54 pm -
1 stop6h 06m
Sun 11/86:04 am -
1 stop3h 56m
Deal found 8/11![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:40 pm -
2 stops6h 45m
Tue 9/1511:10 am -
2 stops8h 50m
Deal found 8/7![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/11. 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 9/116:20 am -
Nonstop2h 07m
Fri 9/186:29 am -
Nonstop2h 06m
Deal found 8/11![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 8/7. 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.
Wed 9/210:04 am -
1 stop6h 40m
Wed 9/911:35 am -
1 stop5h 11m
Deal found 8/7![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:10 am -
1 stop6h 37m
Sun 11/86:04 am -
1 stop3h 56m
Deal found 8/12![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:20 am -
2 stops7h 30m
Wed 9/3010:10 am -
2 stops8h 20m
Deal found 8/12![Southwest logo]()
$335
This United Airlines deal was found by Cheapflights users on 8/11. 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 8/225:43 pm -
Nonstop2h 20m
Sat 8/298:45 am -
1 stop4h 34m
Deal found 8/11![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 8/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:25 am -
1 stop3h 35m
Sun 11/112:55 pm -
2 stops7h 45m
Deal found 8/7![Southwest logo]()
$343
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:33 am -
Nonstop2h 20m
Mon 9/216:15 pm -
Nonstop2h 03m
Deal found 8/10![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:33 am -
Nonstop2h 20m
Mon 9/216:15 pm -
Nonstop2h 03m
Deal found 8/7![United Airlines logo]()
$359
Last-minute flights from Greenville to ChicagoDiscover last-minute flight deals from Greenville to Chicago. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chicago. Data last updated August 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 8/238:37 am -
1 stop29h 13m
Wed 8/268:05 am -
1 stop22h 52m
Deal found 8/9![Multiple Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:40 pm -
2 stops6h 40m
Mon 8/318:00 am -
1 stop3h 30m
Deal found 8/10![Southwest logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:40 pm -
2 stops22h 10m
Sat 8/298:05 am -
1 stop22h 52m
Deal found 8/10![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am -
1 stop4h 50m
Fri 9/43:20 pm -
1 stop5h 15m
Deal found 8/11![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:40 pm -
1 stop5h 20m
Sun 9/68:55 am -
1 stop3h 45m
Deal found 8/10![Southwest logo]()
$274
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:18 pm -
Nonstop2h 12m
Sun 9/610:25 am -
Nonstop2h 07m
Deal found 8/10![United Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:18 pm -
1 stop26h 02m
Sun 9/137:28 pm -
2 stops18h 00m
Deal found 8/7![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:32 pm -
1 stop27h 27m
Thu 9/173:50 pm -
1 stop15h 55m
Deal found 8/11![Multiple Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:40 am -
2 stops7h 50m
Tue 9/226:30 am -
2 stops9h 15m
Deal found 8/10![Southwest logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/173:52 pm -
1 stop8h 07m
Mon 9/217:11 am -
1 stop10h 19m
Deal found 8/9![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Sat 9/268:24 pm -
2 stops19h 21m
Tue 9/297:11 am -
1 stop9h 03m
Deal found 8/9![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:24 pm -
2 stops19h 21m
Fri 10/27:11 am -
1 stop10h 19m
Deal found 8/10![Multiple Airlines logo]()
$273
One-way flights from Greenville to ChicagoSearch for one-way flight options from Greenville to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
Search for one-way flight options from Greenville to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:34 pm -
1 stop20h 16m
Deal found 8/10![Multiple Airlines logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Mon 10/52:50 pm -
1 stop25h 30m
Deal found 8/9![Multiple Airlines logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:18 pm -
1 stop26h 02m
Deal found 8/7![Multiple Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Tue 10/612:29 pm -
1 stop27h 51m
Deal found 8/9![Multiple Airlines logo]()
$94
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:40 pm -
1 stop5h 20m
Deal found 8/10![Southwest logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:24 pm -
2 stops19h 21m
Deal found 8/11![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/143:18 pm -
1 stop25h 02m
Deal found 8/10![Multiple Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:55 pm -
1 stop4h 30m
Deal found 8/10![Southwest logo]()
$125
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:45 am -
2 stops7h 35m
Deal found 8/11![Southwest logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Fri 8/286:41 pm -
2 stops29h 06m
Deal found 8/9![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 8/238:37 am -
2 stops36h 54m
Deal found 8/9![Multiple Airlines logo]()
$143
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 9/66:00 am -
1 stop5h 10m
Deal found 8/7![Delta logo]()
$150
Find flight deals from Greenville to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Greenville (GSP) 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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (Kiwi.com) |
One-way from | $84 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $333 |
Good round-trip deal | $349 or less |
Good one-way deal | $268 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Greenville to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
Use the filters below to find and compare flights from Greenville to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Thu 9/10
6:20 am-7:27 am
Nonstop2h 07m
Chicago O'Hare Intl
Mon 9/14
6:15 pm-9:18 pm
Nonstop2h 03m
$279
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Fri 10/23
5:46 pm-7:05 pm
Nonstop2h 19m
Chicago O'Hare Intl
Sun 10/25
6:29 am-9:30 am
Nonstop2h 01m
$279
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Thu 10/29
10:08 am-2:28 pm
1 stop5h 20m
Chicago O'Hare Intl
Sat 10/31
10:55 am-5:40 pm
1 stop5h 45m
$299
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 9/23
1:20 pm-6:45 pm
1 stop6h 25m
Chicago Midway
Mon 9/28
3:20 pm-9:40 pm
1 stop5h 20m
$299
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Wed 9/30
11:04 am-4:13 pm
1 stop6h 09m
Chicago O'Hare Intl
Sat 10/3
7:05 am-11:59 am
1 stop3h 54m
$299
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 10/14
7:20 pm-10:10 pm
1 stop3h 50m
Chicago Midway
Sat 10/17
6:45 am-12:10 pm
1 stop4h 25m
$299
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Thu 8/27
5:43 pm-7:03 pm
Nonstop2h 20m
Chicago O'Hare Intl
Mon 8/31
5:59 pm-9:07 pm
Nonstop2h 08m
$299
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Wed 9/2
6:00 am-9:23 am
1 stop4h 23m
Chicago O'Hare Intl
Tue 9/8
6:40 am-12:50 pm
1 stop5h 10m
$299
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 8/28
6:55 pm-10:20 pm
1 stop4h 25m
Chicago Midway
Sun 8/30
7:35 am-12:40 pm
1 stop4h 05m
$299
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Tue 8/25
5:43 pm-7:03 pm
Nonstop2h 20m
Chicago O'Hare Intl
Sat 8/29
1:55 pm-5:02 pm
Nonstop2h 07m
$299
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Greenville 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 Greenville 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 Greenville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greenville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Greenville-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Greenville-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 Greenville-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 Greenville to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Greenville with our price prediction graph.
GSP-CHI
GSP-MDW
GSP-ORD
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 Greenville to Chicago
GSP-CHI
GSP-MDW
GSP-ORD
What is the cheapest month to book a flight from Greenville to Chicago?
Currently, February is the cheapest month in which you can book a flight from Greenville to Chicago (average of $279). Flying from Greenville to Chicago in June is currently the most expensive (average of $369). 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 GSP to CHI?
Find hourly flight availability from Greenville 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 12, 2026.
It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 64% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Greenville to Chicago
Explore weekly flight availability from Greenville 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 12, 2026.
The most flights from GSP to CHI are scheduled on a Tuesday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from Greenville to Chicago?
Airfare is below average for this route at the moment.
Greenville to Chicago flights typically cost between $289 and $352 in September.The cheapest round-trip price found within the last 5 days was $269 on Multiple Airlines (Sep 27-Sep 30).
How far ahead should I book a flight from Greenville to Chicago?
To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 86 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Greenville to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Greenville to Chicago. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their Greenville to Chicago flight should consider departing on Wednesday evenings 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.
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 12, 2026.
Read through reviews of airlines operating flights from Greenville to Chicago, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Greenville 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
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Porter
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Other flights to Chicago
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Greenville and Chicago flights
Browse other Greenville and Chicago flight options. Last updated on August 12, 2026.
Other flights from Greenville
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Popular flight searches
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Top 3 airlines flying from Greenville to Chicago
Discover the top 3 airlines that operate flights from Greenville to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$226 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$202 | Average$333 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$302 | FlexibilityNo cancel fee | On-time71% |