$126+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Dec 9 — Dec 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 April, booked 84 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap flight deals from Greenville to Chicago
Cheapest
Best
Last-minute
One-way
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 November 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 November 9, 2026.
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:47 pm -
Nonstop2h 28m
Sat 12/53:15 pm -
Nonstop2h 00m
Deal found 11/4![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/157:05 am -
Nonstop2h 25m
Sat 12/194:59 pm -
Nonstop2h 03m
Deal found 11/5![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:44 am -
1 stop7h 53m
Mon 11/235:26 pm -
2 stops13h 48m
Deal found 11/4![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Fri 11/208:52 pm -
2 stops27h 42m
Fri 11/274:00 pm -
1 stop14h 54m
Deal found 11/8![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Fri 12/1811:43 am -
Nonstop2h 23m
Mon 12/218:46 am -
1 stop5h 39m
Deal found 11/5![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 12/36:47 pm -
Nonstop2h 28m
Mon 12/75:23 am -
1 stop4h 07m
Deal found 11/5![American Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/72:58 pm -
2 stops32h 02m
Mon 12/146:07 am -
1 stop7h 01m
Deal found 11/7![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/48:32 pm -
1 stop13h 46m
Sun 12/66:07 am -
1 stop25h 06m
Deal found 11/6![Multiple Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:36 am -
Nonstop2h 24m
Sun 12/66:54 pm -
Nonstop2h 02m
Deal found 11/4![American Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 11/232:42 pm -
1 stop9h 52m
Fri 11/274:00 pm -
1 stop14h 54m
Deal found 11/8![Multiple Airlines logo]()
$338
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Wed 11/257:43 pm -
1 stop5h 19m
Mon 11/305:55 pm -
Nonstop2h 03m
Deal found 11/4![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/5. 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 12/312:18 pm -
1 stop4h 58m
Mon 12/76:00 am -
1 stop4h 13m
Deal found 11/5![Delta logo]()
$339
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 November 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 November 9, 2026.
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Sat 12/510:27 am -
Nonstop2h 10m
Tue 12/88:52 am -
1 stop4h 36m
Deal found 11/4![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 11/5. 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.
Tue 1/55:38 am -
1 stop5h 32m
Wed 1/65:07 pm -
1 stop5h 46m
Deal found 11/5![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 11/4. 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.
Tue 1/128:25 am -
1 stop7h 20m
Fri 1/153:50 pm -
1 stop5h 50m
Deal found 11/4![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Tue 12/227:37 pm -
1 stop5h 24m
Sat 1/25:50 pm -
Nonstop2h 01m
Deal found 11/4![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 12/47:25 pm -
1 stop4h 29m
Fri 12/111:02 pm -
1 stop5h 55m
Deal found 11/4![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:05 am -
1 stop10h 10m
Fri 1/18:00 am -
1 stop5h 10m
Deal found 11/5![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/22:04 pm -
Nonstop2h 11m
Mon 12/71:49 pm -
Nonstop2h 04m
Deal found 11/6![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/6. 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.
Thu 12/310:27 am -
1 stop5h 22m
Mon 12/75:02 pm -
1 stop3h 47m
Deal found 11/6![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/8. 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 1/167:00 am -
1 stop4h 45m
Sun 1/1710:00 am -
2 stops8h 40m
Deal found 11/8![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 11/6. 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.
Wed 4/285:05 pm -
1 stop6h 05m
Mon 5/36:00 am -
1 stop3h 58m
Deal found 11/6![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/8. 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.
Mon 1/187:30 am -
2 stops6h 30m
Tue 1/192:25 pm -
1 stop5h 35m
Deal found 11/8![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:43 pm -
1 stop5h 19m
Sat 11/286:29 am -
Nonstop2h 01m
Deal found 11/5![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 11/8. 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 3/57:10 am -
1 stop6h 51m
Mon 3/85:25 pm -
1 stop5h 12m
Deal found 11/8![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/8. 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 1/167:00 am -
1 stop4h 45m
Tue 1/1910:00 am -
2 stops10h 00m
Deal found 11/8![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Thu 11/1910:26 am -
1 stop5h 12m
Mon 11/235:55 pm -
Nonstop2h 03m
Deal found 11/4![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 11/5. 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 12/2412:44 pm -
1 stop10h 38m
Fri 1/16:00 am -
1 stop3h 48m
Deal found 11/5![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Tue 12/17:48 pm -
1 stop4h 41m
Thu 12/36:50 am -
Nonstop2h 02m
Deal found 11/8![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 11/5. 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.
Tue 11/245:40 am -
1 stop4h 42m
Tue 11/242:44 pm -
1 stop5h 49m
Deal found 11/5![Delta logo]()
$429
This United Airlines deal was found by Cheapflights users on 11/5. 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 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
Sun 11/296:29 am -
Nonstop2h 01m
Deal found 11/5![United Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 11/7. 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.
Tue 12/1510:57 am -
1 stop6h 20m
Tue 12/225:25 am -
1 stop15h 12m
Deal found 11/7![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Tue 11/2410:26 am -
2 stops6h 23m
Tue 11/245:55 pm -
Nonstop2h 03m
Deal found 11/8![United Airlines logo]()
$448
Last-minute flights from Greenville to ChicagoDiscover last-minute flight deals from Greenville to Chicago. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chicago. Data last updated November 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:44 am -
1 stop7h 53m
Mon 11/235:26 pm -
2 stops13h 48m
Deal found 11/4![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Fri 11/208:52 pm -
2 stops27h 42m
Fri 11/274:00 pm -
1 stop14h 54m
Deal found 11/8![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 11/232:42 pm -
1 stop9h 52m
Fri 11/274:00 pm -
1 stop14h 54m
Deal found 11/8![Multiple Airlines logo]()
$338
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Wed 11/257:43 pm -
1 stop5h 19m
Mon 11/305:55 pm -
Nonstop2h 03m
Deal found 11/4![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:47 pm -
Nonstop2h 28m
Sat 12/53:15 pm -
Nonstop2h 00m
Deal found 11/4![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 12/36:47 pm -
Nonstop2h 28m
Mon 12/75:23 am -
1 stop4h 07m
Deal found 11/5![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 11/5. 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 12/312:18 pm -
1 stop4h 58m
Mon 12/76:00 am -
1 stop4h 13m
Deal found 11/5![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/48:32 pm -
1 stop13h 46m
Sun 12/66:07 am -
1 stop25h 06m
Deal found 11/6![Multiple Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:36 am -
Nonstop2h 24m
Sun 12/66:54 pm -
Nonstop2h 02m
Deal found 11/4![American Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/72:58 pm -
2 stops32h 02m
Mon 12/146:07 am -
1 stop7h 01m
Deal found 11/7![Multiple Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/157:05 am -
Nonstop2h 25m
Sat 12/194:59 pm -
Nonstop2h 03m
Deal found 11/5![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Fri 12/1811:43 am -
Nonstop2h 23m
Mon 12/218:46 am -
1 stop5h 39m
Deal found 11/5![American Airlines logo]()
$329
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 November 9, 2026.
Search for one-way flight options from Greenville to Chicago. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/148:52 pm -
3 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/153:30 pm -
1 stop25h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:27 pm -
2 stops30h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/72:42 pm -
2 stops21h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:28 am -
2 stops28h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop7h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/811:28 am -
3 stops25h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:36 am -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![American Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/238:52 pm -
2 stops27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
2 stops16h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$170
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/171:05 pm -
2 stops6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/153:30 pm -
2 stops33h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$176
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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (American Airlines) |
One-way from | $126 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $343 |
Good round-trip deal | $395 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 November 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
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Mon 12/7
2:42 pm-10:00 pm
2 stops32h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Tue 12/8
11:28 am-2:30 pm
2 stops28h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Quickest round-trip
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Wed 2/17
5:48 pm-7:05 pm
Nonstop2h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Sat 12/12
12:59 pm-4:17 pm
1 stop4h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 2/17
5:30 pm-10:45 pm
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Sat 11/21
5:06 pm-8:14 am
2 stops16h 08m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 2/17
1:05 pm-6:35 pm
2 stops6h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$175
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Mon 2/15
3:30 pm-11:46 pm
2 stops33h 16m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$176
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Mon 12/7
2:50 pm-6:55 pm
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
GreenvilleChicago
GSP Greenville - ORD Chicago O'Hare Intl
GSPORD
Greenville
Thu 12/10
5:34 pm-7:00 pm
Nonstop2h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$210
Showing 1-10 of 39 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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, March is the cheapest month in which you can book a flight from Greenville to Chicago (average of $283). Flying from Greenville to Chicago in October is currently the most expensive (average of $385). 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 November 9, 2026.
It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 51% 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 November 9, 2026.
The most flights from GSP to CHI are scheduled on a Monday (28 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (23 on average).
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 $299 and $446 in January.The cheapest round-trip price found within the last 5 days was $319 on American Airlines (Jan 27-Jan 29).
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 42 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 November 7, 2026.
Travelers seeking maximum savings on their Greenville to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons 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 November 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.
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - 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
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Greenville
Popular flights
Alternative routes for Greenville to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 9, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Greenville to Chicago by cabin class
Find flights from Greenville to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Greenville and Chicago flights
Browse other Greenville and Chicago flight options. Last updated on November 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 November 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$226 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$318 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$218 | Average$370 | FlexibilityNo cancel fee | On-time69% |