$97+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Jul 11 — Jul 181
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 November, booked 52 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 June 11, 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 June 11, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Wed 7/16:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Fri 7/31:55 pm
ORD
- GSP
Nonstop2h 05m
United Airlines
Deal found 6/9![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1111:46 am
GSP
- ORD
Nonstop2h 09m
American Airlines
Mon 7/138:59 pm
ORD
- GSP
Nonstop1h 59m
American Airlines
Deal found 6/10![American Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 6/10. 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 8/64:40 pm
GSP
- MDW
1 stop5h 20m
Southwest
Sun 8/97:30 am
MDW
- GSP
1 stop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$270
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 7/236:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Tue 8/41:55 pm
ORD
- GSP
Nonstop2h 05m
United Airlines
Deal found 6/9![United Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 9/27:39 am
GSP
- ORD
Nonstop2h 21m
American Airlines
Tue 9/83:05 pm
ORD
- GSP
Nonstop1h 59m
American Airlines
Deal found 6/8![American Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 8/276:55 pm
GSP
- MDW
1 stop4h 25m
Southwest
Sun 8/305:00 am
MDW
- GSP
1 stop4h 10m
Southwest
Deal found 6/8![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/75:43 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Sun 8/96:55 am
ORD
- GSP
Nonstop2h 00m
United Airlines
Deal found 6/10![United Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 7/46:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Mon 7/66:17 pm
ORD
- GSP
Nonstop2h 09m
United Airlines
Deal found 6/8![United Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:18 pm
GSP
- ORD
1 stop4h 42m
American Airlines
Sun 7/268:59 pm
ORD
- GSP
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:14 pm
GSP
- ORD
Nonstop2h 16m
American Airlines
Mon 11/26:35 pm
ORD
- GSP
1 stop4h 23m
American Airlines
Deal found 6/9![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:43 pm
GSP
- ORD
Nonstop2h 31m
American Airlines
Sun 7/55:07 am
ORD
- GSP
1 stop4h 05m
American Airlines
Deal found 6/10![American Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 6/8. 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 8/171:05 pm
GSP
- MDW
2 stops7h 25m
Southwest
Fri 8/2110:25 am
MDW
- GSP
2 stops6h 55m
Southwest
Deal found 6/8![Southwest logo]()
$283
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 June 11, 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 June 11, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 10/86:20 am
GSP
- ORD
Nonstop2h 09m
United Airlines
Sun 10/116:55 am
ORD
- GSP
Nonstop2h 03m
United Airlines
Deal found 6/9![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 6/10. 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 8/64:40 pm
GSP
- MDW
1 stop5h 20m
Southwest
Sun 8/97:30 am
MDW
- GSP
1 stop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 8/285:20 pm
GSP
- ORD
1 stop4h 35m
Delta
Sat 8/296:40 am
ORD
- GSP
1 stop5h 01m
Delta
Deal found 6/10![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 7/46:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Mon 7/66:17 pm
ORD
- GSP
Nonstop2h 09m
United Airlines
Deal found 6/9![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 8/274:40 pm
GSP
- MDW
2 stops6h 40m
Southwest
Sun 8/305:00 am
MDW
- GSP
1 stop4h 10m
Southwest
Deal found 6/8![Southwest logo]()
$281
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 10/65:40 am
GSP
- MDW
1 stop5h 12m
Delta
Sat 10/106:00 am
MDW
- GSP
1 stop6h 08m
Delta
Deal found 6/10![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/75:43 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Sun 8/96:55 am
ORD
- GSP
Nonstop2h 00m
United Airlines
Deal found 6/10![United Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 6/8. 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 8/171:05 pm
GSP
- MDW
2 stops7h 25m
Southwest
Fri 8/2110:25 am
MDW
- GSP
2 stops6h 55m
Southwest
Deal found 6/8![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 7/117:10 am
GSP
- MDW
1 stop6h 28m
Delta
Wed 7/1511:05 am
MDW
- GSP
1 stop4h 02m
Delta
Deal found 6/9![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/75:43 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Sat 7/116:17 pm
ORD
- GSP
Nonstop2h 09m
United Airlines
Deal found 6/8![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:00 am
GSP
- MDW
1 stop5h 00m
Southwest
Wed 7/1511:25 am
MDW
- GSP
2 stops7h 55m
Southwest
Deal found 6/9![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 6/8. 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 8/67:15 am
GSP
- MDW
1 stop6h 24m
Delta
Sun 8/96:05 am
MDW
- GSP
1 stop5h 36m
Delta
Deal found 6/8![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 6/6. 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.
Sat 6/275:43 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Sat 7/41:55 pm
ORD
- GSP
Nonstop2h 05m
United Airlines
Deal found 6/6![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 8/145:20 pm
GSP
- MDW
1 stop6h 16m
Delta
Sun 8/166:05 am
MDW
- GSP
1 stop5h 36m
Delta
Deal found 6/7![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/251:55 pm
GSP
- MDW
2 stops6h 20m
Southwest
Sat 8/16:35 am
MDW
- GSP
1 stop4h 40m
Southwest
Deal found 6/9![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/16:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Mon 7/66:17 pm
ORD
- GSP
Nonstop2h 09m
United Airlines
Deal found 6/8![United Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/77:40 pm
GSP
- ORD
1 stop4h 51m
United Airlines
Mon 7/136:55 am
ORD
- GSP
Nonstop2h 00m
United Airlines
Deal found 6/8![United Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Wed 7/155:43 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Tue 7/218:40 am
ORD
- GSP
1 stop4h 40m
United Airlines
Deal found 6/7![United Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 9/117:30 pm
GSP
- ORD
1 stop5h 10m
United Airlines
Wed 9/168:45 am
ORD
- GSP
1 stop4h 35m
United Airlines
Deal found 6/9![United Airlines logo]()
$289
Last-minute flights from Greenville to ChicagoDiscover last-minute flight deals from Greenville to Chicago. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chicago. Data last updated June 11, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Wed 7/16:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Fri 7/31:55 pm
ORD
- GSP
Nonstop2h 05m
United Airlines
Deal found 6/9![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 7/17:50 pm
GSP
- MDW
1 stop4h 20m
Southwest
Sun 7/56:10 am
MDW
- GSP
1 stop5h 00m
Southwest
Deal found 6/10![Southwest logo]()
$289
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:32 pm
GSP
- ORD
1 stop5h 29m
American Airlines
Sat 7/46:58 am
ORD
- GSP
1 stop4h 46m
American Airlines
Deal found 6/10![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:43 pm
GSP
- ORD
Nonstop2h 31m
American Airlines
Sun 7/55:07 am
ORD
- GSP
1 stop4h 05m
American Airlines
Deal found 6/10![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:18 pm
GSP
- ORD
1 stop4h 42m
American Airlines
Mon 7/68:59 pm
ORD
- GSP
Nonstop1h 59m
American Airlines
Deal found 6/7![American Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 6/11. 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 7/46:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Mon 7/66:17 pm
ORD
- GSP
Nonstop2h 09m
United Airlines
Deal found 6/11![United Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:20 pm
GSP
- ORD
Nonstop2h 31m
American Airlines
Mon 7/136:47 pm
ORD
- GSP
1 stop4h 04m
American Airlines
Deal found 6/10![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1111:46 am
GSP
- ORD
Nonstop2h 09m
American Airlines
Mon 7/138:59 pm
ORD
- GSP
Nonstop1h 59m
American Airlines
Deal found 6/10![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 7/116:00 pm
GSP
- ORD
1 stop5h 00m
American Airlines
Wed 7/153:48 pm
ORD
- GSP
Nonstop2h 02m
American Airlines
Deal found 6/8![American Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 7/1112:46 pm
GSP
- MDW
1 stop6h 21m
Delta
Wed 7/1511:05 am
MDW
- GSP
1 stop4h 02m
Delta
Deal found 6/8![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/147:00 am
GSP
- MDW
2 stops9h 10m
Southwest
Wed 7/157:25 am
MDW
- GSP
1 stop4h 45m
Southwest
Deal found 6/10![Southwest logo]()
$294
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 7/236:10 am
GSP
- ORD
Nonstop2h 20m
United Airlines
Tue 8/41:55 pm
ORD
- GSP
Nonstop2h 05m
United Airlines
Deal found 6/9![United Airlines logo]()
$271
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 June 11, 2026.
Search for one-way flight options from Greenville to Chicago. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 8/127:00 am
GSP
- MDW
1 stop4h 55m
Southwest
Deal found 6/10![Southwest logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/104:57 pm
GSP
- ORD
1 stop20h 18m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$108
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:50 am
GSP
- MDW
1 stop5h 15m
Southwest
Deal found 6/9![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 8/74:57 pm
GSP
- ORD
1 stop20h 18m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 9/78:28 pm
GSP
- ORD
1 stop27h 46m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 9/38:37 am
GSP
- ORD
1 stop28h 48m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$122
This Southwest deal was found by Cheapflights users on 6/10. 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 8/136:55 pm
GSP
- MDW
1 stop4h 25m
Southwest
Deal found 6/10![Southwest logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/68:37 am
GSP
- ORD
1 stop28h 38m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 7/13:48 pm
GSP
- ORD
1 stop21h 36m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/313:31 pm
GSP
- ORD
1 stop21h 44m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 6/11. 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 7/87:40 pm
GSP
- MDW
1 stop4h 35m
Southwest
Deal found 6/11![Southwest logo]()
$145
This Southwest deal was found by Cheapflights users on 6/7. 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.
Tue 7/148:25 am
GSP
- MDW
1 stop6h 35m
Southwest
Deal found 6/7![Southwest logo]()
$148
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 June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (United Airlines) |
One-way from | $97 (Southwest) |
Popular in | March |
Cheapest in | February |
Average price | $351 |
Good round-trip deal | $357 or less |
Good one-way deal | $273 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 June 11, 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 - ORD
GSPORD
Greenville
Thu 10/8
6:20 am-7:29 am
Nonstop2h 09m
Chicago O'Hare Intl
Sun 10/11
6:55 am-9:58 am
Nonstop2h 03m
$269
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Sat 7/4
6:10 am-7:30 am
Nonstop2h 20m
Chicago O'Hare Intl
Mon 7/6
6:17 pm-9:26 pm
Nonstop2h 09m
$269
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Thu 8/6
4:40 pm-9:00 pm
1 stop5h 20m
Chicago Midway
Sun 8/9
7:30 am-12:40 pm
1 stop4h 10m
$270
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Fri 8/7
5:43 pm-7:00 pm
Nonstop2h 17m
Chicago O'Hare Intl
Sun 8/9
6:55 am-9:55 am
Nonstop2h 00m
$276
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Tue 7/7
5:43 pm-7:00 pm
Nonstop2h 17m
Chicago O'Hare Intl
Sat 7/11
6:17 pm-9:26 pm
Nonstop2h 09m
$277
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Sat 6/27
5:43 pm-7:00 pm
Nonstop2h 17m
Chicago O'Hare Intl
Sat 7/4
1:55 pm-5:00 pm
Nonstop2h 05m
$277
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Wed 7/1
6:10 am-7:30 am
Nonstop2h 20m
Chicago O'Hare Intl
Mon 7/6
6:17 pm-9:26 pm
Nonstop2h 09m
$277
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Tue 7/7
7:40 pm-11:31 pm
1 stop4h 51m
Chicago O'Hare Intl
Mon 7/13
6:55 am-9:55 am
Nonstop2h 00m
$279
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Thu 8/27
4:40 pm-10:20 pm
2 stops6h 40m
Chicago Midway
Sun 8/30
5:00 am-10:10 am
1 stop4h 10m
$281
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Mon 8/17
1:05 pm-7:30 pm
2 stops7h 25m
Chicago Midway
Fri 8/21
10:25 am-6:20 pm
2 stops6h 55m
$283
Showing 1-10 of 37 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 June.
| 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, November is the cheapest month in which you can book a flight from Greenville to Chicago (average of $81). Flying from Greenville to Chicago in January is currently the most expensive (average of $195). 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 June 11, 2026.
It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 67% 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 June 11, 2026.
The most flights from GSP to CHI are scheduled on a Monday (22 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?
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 88 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 June 8, 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. 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 June 11, 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
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Food
7.2
Overall
7.9
Entertainment
7.8
Comfort
7.8
Crew
8.5
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
Hammond
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 June 11, 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 June 11, 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 June 11, 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 2,558,603 searches. Data last updated June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$107 | Average$226 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$202 | Average$315 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$202 | Average$291 | FlexibilityNo cancel fee | On-time71% |