$127+ Cheap flights from Greenville (GSP) 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Oct 9 — Oct 161
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 18 days in advance, depart on a Saturday or Friday 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 September 9, 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 September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1312:29 pm -
1 stop28h 01m
Mon 10/198:04 am -
1 stop9h 36m
Deal found 9/9![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/102:30 pm -
1 stop18h 01m
Thu 10/158:26 am -
1 stop10h 33m
Deal found 9/9![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/212:11 pm -
1 stop28h 09m
Tue 10/67:11 am -
1 stop9h 08m
Deal found 9/6![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/283:18 pm -
1 stop25h 02m
Fri 10/27:11 am -
2 stops35h 33m
Deal found 9/6![Multiple Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/611:38 am -
Nonstop2h 16m
Sat 10/103:06 pm -
Nonstop2h 02m
Deal found 9/5![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/31:11 pm -
Nonstop2h 15m
Tue 10/67:54 pm -
Nonstop2h 06m
Deal found 9/5![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/283:18 pm -
1 stop25h 02m
Sat 10/37:11 am -
2 stops25h 21m
Deal found 9/6![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/128:32 pm -
2 stops22h 59m
Mon 10/198:04 am -
1 stop9h 36m
Deal found 9/9![Multiple Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/306:23 pm -
Nonstop2h 36m
Sun 10/46:45 am -
1 stop6h 17m
Deal found 9/5![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:01 am -
Nonstop2h 34m
Fri 11/271:13 pm -
Nonstop1h 59m
Deal found 9/8![American Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 10/115:40 am -
1 stop5h 23m
Wed 10/216:04 am -
1 stop3h 56m
Deal found 9/9![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/263:30 pm -
1 stop4h 50m
Tue 9/298:15 am -
2 stops7h 30m
Deal found 9/4![Southwest logo]()
$324
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 September 9, 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 September 9, 2026.
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:00 am -
1 stop6h 51m
Sun 11/226:00 am -
1 stop4h 07m
Deal found 9/9![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/76:45 pm -
1 stop4h 55m
Thu 12/1012:50 pm -
1 stop6h 00m
Deal found 9/6![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/46:20 am -
Nonstop2h 09m
Sun 10/116:55 am -
Nonstop2h 03m
Deal found 9/4![United Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:20 am -
1 stop6h 27m
Tue 11/311:39 am -
1 stop6h 18m
Deal found 9/9![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/7. 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.
Thu 10/298:40 pm -
1 stop4h 15m
Mon 11/24:00 pm -
1 stop5h 55m
Deal found 9/7![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:05 am -
1 stop4h 54m
Mon 11/161:05 pm -
1 stop4h 09m
Deal found 9/8![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/7. 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.
Sat 10/105:46 pm -
Nonstop2h 19m
Sun 10/116:25 pm -
Nonstop2h 00m
Deal found 9/7![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:20 am -
1 stop6h 39m
Sat 11/78:05 am -
1 stop5h 49m
Deal found 9/8![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:37 pm -
Nonstop2h 23m
Thu 12/36:50 am -
Nonstop2h 02m
Deal found 9/6![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/107:20 am -
1 stop4h 04m
Tue 10/135:27 am -
1 stop6h 33m
Deal found 9/5![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:43 pm -
1 stop5h 18m
Wed 11/255:55 pm -
Nonstop2h 03m
Deal found 9/8![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/275:45 am -
1 stop3h 51m
Sat 10/35:30 am -
1 stop3h 40m
Deal found 9/6![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/105:40 am -
1 stop5h 49m
Sun 12/136:00 am -
1 stop4h 13m
Deal found 9/5![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/7. 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.
Sat 10/32:51 pm -
1 stop4h 50m
Wed 10/71:55 pm -
Nonstop2h 10m
Deal found 9/7![United Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/912:18 pm -
1 stop4h 59m
Sun 12/136:00 am -
1 stop6h 22m
Deal found 9/5![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/312:49 pm -
1 stop6h 33m
Tue 10/66:04 am -
1 stop5h 56m
Deal found 9/6![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:35 pm -
2 stops13h 02m
Sat 10/1012:55 pm -
1 stop5h 05m
Deal found 9/9![United Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/67:20 am -
1 stop6h 27m
Sat 10/104:19 pm -
1 stop5h 32m
Deal found 9/6![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/307:00 am -
1 stop3h 49m
Sat 10/36:05 am -
1 stop5h 45m
Deal found 9/5![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1112:18 pm -
1 stop4h 59m
Sun 12/136:00 am -
1 stop4h 13m
Deal found 9/5![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:05 am -
1 stop4h 19m
Mon 11/305:13 pm -
1 stop5h 40m
Deal found 9/6![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:12 pm -
1 stop5h 53m
Mon 11/306:15 pm -
1 stop4h 38m
Deal found 9/5![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 9/7. 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.
Thu 9/178:05 am -
1 stop5h 36m
Mon 9/211:55 pm -
1 stop6h 31m
Deal found 9/7![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:40 am -
1 stop4h 42m
Wed 11/251:30 pm -
1 stop3h 49m
Deal found 9/4![Delta logo]()
$487
Last-minute flights from Greenville to ChicagoDiscover last-minute flight deals from Greenville to Chicago. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chicago. Data last updated September 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/263:30 pm -
1 stop4h 50m
Tue 9/298:15 am -
2 stops7h 30m
Deal found 9/4![Southwest logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/283:18 pm -
1 stop25h 02m
Fri 10/27:11 am -
2 stops35h 33m
Deal found 9/6![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/283:18 pm -
1 stop25h 02m
Sat 10/37:11 am -
2 stops25h 21m
Deal found 9/6![Multiple Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/306:23 pm -
Nonstop2h 36m
Sun 10/46:45 am -
1 stop6h 17m
Deal found 9/5![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/212:11 pm -
1 stop28h 09m
Tue 10/67:11 am -
1 stop9h 08m
Deal found 9/6![Multiple Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/31:11 pm -
Nonstop2h 15m
Tue 10/67:54 pm -
Nonstop2h 06m
Deal found 9/5![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/611:38 am -
Nonstop2h 16m
Sat 10/103:06 pm -
Nonstop2h 02m
Deal found 9/5![American Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/102:30 pm -
1 stop18h 01m
Thu 10/158:26 am -
1 stop10h 33m
Deal found 9/9![Multiple Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 10/115:40 am -
1 stop5h 23m
Wed 10/216:04 am -
1 stop3h 56m
Deal found 9/9![Delta logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/128:32 pm -
2 stops22h 59m
Mon 10/198:04 am -
1 stop9h 36m
Deal found 9/9![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1312:29 pm -
1 stop28h 01m
Mon 10/198:04 am -
1 stop9h 36m
Deal found 9/9![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1312:29 pm -
1 stop28h 01m
Tue 10/206:00 am -
2 stops8h 29m
Deal found 9/9![Multiple Airlines logo]()
$313
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 September 9, 2026.
Search for one-way flight options from Greenville to Chicago. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 9/287:03 pm -
2 stops21h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/57:08 pm -
2 stops21h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/9. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:32 pm -
2 stops17h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$147
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:23 pm -
Nonstop2h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![American Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/78:24 pm -
2 stops20h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/286:55 pm -
1 stop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 1/167:55 am -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/212:11 pm -
2 stops30h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/110:12 am -
3 stops14h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:32 pm -
2 stops21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/78:24 pm -
3 stops22h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$180
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 September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Kiwi.com) |
One-way from | $127 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $311 |
Good round-trip deal | $356 or less |
Good one-way deal | $288 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 7,457,451 searches. Data last updated September 9, 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
Mon 10/19
6:20 am-7:29 am
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Mon 10/12
6:43 pm-8:13 pm
Nonstop2h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Thu 10/8
6:20 am-7:29 am
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Mon 12/7
8:06 am-12:20 pm
1 stop5h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Mon 9/28
6:55 pm-10:25 pm
1 stop4h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Wed 10/7
11:05 am-4:32 pm
1 stop6h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Thu 10/1
8:40 pm-11:55 pm
1 stop4h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Mon 9/28
7:35 pm-11:32 pm
1 stop4h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Mon 10/26
8:40 pm-11:55 pm
1 stop4h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Sat 1/16
7:55 am-3:10 pm
1 stop8h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$165
Showing 1-10 of 45 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 September.
| 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-ORD
GSP-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 Greenville to Chicago
GSP-CHI
GSP-ORD
GSP-MDW
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 $282). 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 September 9, 2026.
It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 58% on the flight price compared to flying at noon, which is usually more expensive.
How much does it cost to fly round-trip from Greenville to Chicago?
Airfare is typical for this route at the moment.
Greenville to Chicago flights typically cost between $269 and $344 in October.The cheapest round-trip price found within the last 5 days was $281 on Multiple Airlines (Oct 23-Oct 26).
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 17 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 September 5, 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 September 9, 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
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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
Merrillville
Lansing
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 September 9, 2026.
Other flights from Greenville
Browse through other flights departing from Greenville. Flights are based on user searches made on Cheapflights and were last updated on September 9, 2026.
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 7,457,451 searches. Data last updated September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$226 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$202 | Average$350 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$303 | FlexibilityNo cancel fee | On-time71% |