$93+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Mar 13 — Mar 201
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 April, booked 60 days in advance, depart on a Thursday or Saturday and return on a Saturday
Cheap flight deals from Greenville to Chicago
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Best
Last-minute
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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 February 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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 3/77:20 am
GSP
- ORD
1 stop7h 00m
Delta
Wed 3/115:30 am
ORD
- GSP
1 stop4h 35m
Delta
Deal found 2/9![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 2/9. 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 3/77:20 am
GSP
- MDW
1 stop6h 26m
Delta
Wed 3/116:07 pm
MDW
- GSP
1 stop4h 47m
Delta
Deal found 2/9![Delta logo]()
$147
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 3/76:30 am
GSP
- ORD
Nonstop2h 23m
United Airlines
Wed 3/111:55 pm
ORD
- GSP
Nonstop1h 56m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 3/26:49 pm
GSP
- ORD
2 stops17h 58m
Multiple Airlines
Wed 3/48:16 pm
ORD
- GSP
1 stop18h 35m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$210
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Sat 3/217:40 am
GSP
- ORD
Nonstop2h 16m
American Airlines
Mon 3/238:50 pm
ORD
- GSP
Nonstop1h 52m
American Airlines
Deal found 2/9![American Airlines logo]()
$211
This American Airlines deal was found by Cheapflights users on 2/9. 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 5/18:14 pm
GSP
- ORD
Nonstop2h 22m
American Airlines
Wed 5/69:00 pm
ORD
- GSP
Nonstop1h 59m
American Airlines
Deal found 2/9![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 2/9. 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.
Thu 4/237:59 pm
GSP
- ORD
1 stop5h 00m
Delta
Sun 4/265:10 am
ORD
- GSP
1 stop4h 10m
Delta
Deal found 2/9![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 2/9. 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.
Thu 3/57:20 am
GSP
- MDW
1 stop6h 26m
Delta
Sun 3/86:00 am
MDW
- GSP
1 stop4h 05m
Delta
Deal found 2/9![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 2/256:00 am
GSP
- ORD
1 stop5h 45m
Delta
Sat 3/710:35 am
ORD
- GSP
1 stop6h 09m
Delta
Deal found 2/10![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:20 am
GSP
- MDW
1 stop6h 26m
Delta
Wed 3/46:00 am
MDW
- GSP
1 stop4h 13m
Delta
Deal found 2/11![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/9. 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 4/97:42 pm
GSP
- ORD
1 stop5h 01m
United Airlines
Sun 4/127:00 am
ORD
- GSP
Nonstop1h 56m
United Airlines
Deal found 2/9![United Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 3/215:32 pm
GSP
- ORD
Nonstop2h 28m
United Airlines
Tue 3/248:50 am
ORD
- GSP
1 stop4h 27m
United Airlines
Deal found 2/10![United Airlines logo]()
$222
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 February 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/8. 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 3/77:20 am
GSP
- MDW
1 stop6h 26m
Delta
Wed 3/116:07 pm
MDW
- GSP
1 stop4h 47m
Delta
Deal found 2/8![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 2/8. 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 3/217:40 am
GSP
- ORD
Nonstop2h 16m
American Airlines
Sat 3/287:22 pm
ORD
- GSP
Nonstop1h 52m
American Airlines
Deal found 2/8![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/8. 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 4/2212:33 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Sat 4/251:55 pm
ORD
- GSP
Nonstop1h 59m
United Airlines
Deal found 2/8![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sun 4/198:00 am
GSP
- MDW
1 stop6h 45m
Southwest
Thu 4/237:10 am
MDW
- GSP
1 stop5h 05m
Southwest
Deal found 2/9![Southwest logo]()
$229
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/68:21 pm
GSP
- ORD
Nonstop2h 19m
American Airlines
Mon 3/98:00 am
ORD
- GSP
Nonstop1h 56m
American Airlines
Deal found 2/10![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:30 am
GSP
- ORD
Nonstop2h 23m
United Airlines
Sun 3/157:05 am
ORD
- GSP
Nonstop1h 56m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/8. 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 4/235:21 pm
GSP
- MDW
1 stop6h 07m
Delta
Sun 4/266:00 am
MDW
- GSP
1 stop5h 21m
Delta
Deal found 2/8![Delta logo]()
$213
This Southwest deal was found by Cheapflights users on 2/10. 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 4/71:55 pm
GSP
- MDW
1 stop6h 35m
Southwest
Wed 4/84:50 pm
MDW
- GSP
1 stop3h 50m
Southwest
Deal found 2/10![Southwest logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:33 pm
GSP
- ORD
Nonstop2h 17m
United Airlines
Sun 4/268:40 am
ORD
- GSP
Nonstop2h 04m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/9. 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.
Thu 5/217:20 am
GSP
- MDW
1 stop6h 22m
Delta
Tue 5/266:30 am
MDW
- GSP
1 stop4h 33m
Delta
Deal found 2/9![Delta logo]()
$213
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/66:30 am
GSP
- ORD
Nonstop2h 23m
United Airlines
Sun 3/87:05 am
ORD
- GSP
Nonstop1h 56m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
GSP
- ORD
1 stop5h 45m
Delta
Sat 3/710:35 am
ORD
- GSP
1 stop6h 09m
Delta
Deal found 2/10![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/10. 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 2/275:40 am
GSP
- ORD
1 stop3h 55m
Delta
Sat 3/710:35 am
ORD
- GSP
1 stop6h 09m
Delta
Deal found 2/10![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/10. 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 4/106:30 am
GSP
- ORD
Nonstop2h 24m
United Airlines
Sat 4/111:00 pm
ORD
- GSP
1 stop4h 59m
United Airlines
Deal found 2/10![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 3/116:05 am
GSP
- ORD
1 stop6h 10m
Delta
Wed 3/189:35 am
ORD
- GSP
1 stop7h 06m
Delta
Deal found 2/10![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:42 pm
GSP
- ORD
1 stop5h 01m
United Airlines
Sun 4/128:40 am
ORD
- GSP
Nonstop2h 04m
United Airlines
Deal found 2/10![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/10. 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.
Sun 3/17:20 am
GSP
- ORD
1 stop7h 00m
Delta
Sat 3/710:35 am
ORD
- GSP
1 stop6h 09m
Delta
Deal found 2/10![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:20 am
GSP
- MDW
1 stop6h 26m
Delta
Wed 3/46:00 am
MDW
- GSP
1 stop4h 13m
Delta
Deal found 2/11![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:20 am
GSP
- MDW
1 stop6h 26m
Delta
Sun 3/86:00 am
MDW
- GSP
1 stop4h 05m
Delta
Deal found 2/10![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:20 am
GSP
- MDW
1 stop6h 26m
Delta
Sun 3/86:00 am
MDW
- GSP
1 stop4h 05m
Delta
Deal found 2/11![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 4/225:50 pm
GSP
- MDW
1 stop5h 38m
Delta
Sun 4/266:00 am
MDW
- GSP
1 stop5h 21m
Delta
Deal found 2/10![Delta logo]()
$223
Last-minute flights from Greenville to ChicagoDiscover last-minute flight deals from Greenville to Chicago. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chicago. Data last updated February 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 2/187:29 am
GSP
- ORD
Nonstop2h 16m
American Airlines
Fri 2/277:22 pm
ORD
- GSP
Nonstop1h 52m
American Airlines
Deal found 2/10![American Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Thu 2/196:30 am
GSP
- ORD
Nonstop2h 23m
United Airlines
Sat 2/217:05 am
ORD
- GSP
Nonstop1h 56m
United Airlines
Deal found 2/8![United Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Fri 2/208:21 pm
GSP
- ORD
Nonstop2h 19m
American Airlines
Sun 2/228:00 am
ORD
- GSP
Nonstop1h 56m
American Airlines
Deal found 2/8![American Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 2/9. 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 2/207:07 am
GSP
- ORD
1 stop7h 12m
American Airlines
Mon 2/238:03 am
ORD
- GSP
Nonstop1h 56m
American Airlines
Deal found 2/9![American Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 2/9. 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 2/207:40 pm
GSP
- ORD
1 stop5h 16m
Delta
Mon 2/236:45 am
ORD
- GSP
1 stop6h 17m
Delta
Deal found 2/9![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:19 am
GSP
- MDW
1 stop4h 40m
Delta
Mon 3/26:40 pm
MDW
- GSP
1 stop4h 03m
Delta
Deal found 2/11![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 2/11. 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.
Fri 2/274:25 pm
GSP
- MDW
1 stop7h 45m
Southwest
Tue 3/31:15 pm
MDW
- GSP
1 stop5h 35m
Southwest
Deal found 2/11![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:20 am
GSP
- MDW
1 stop6h 26m
Delta
Wed 3/46:00 am
MDW
- GSP
1 stop4h 13m
Delta
Deal found 2/11![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/9. 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.
Thu 3/57:20 am
GSP
- MDW
1 stop6h 26m
Delta
Sun 3/86:00 am
MDW
- GSP
1 stop4h 05m
Delta
Deal found 2/9![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 2/9. 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 3/77:20 am
GSP
- MDW
1 stop6h 26m
Delta
Wed 3/116:07 pm
MDW
- GSP
1 stop4h 47m
Delta
Deal found 2/9![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 3/96:25 pm
GSP
- MDW
1 stop6h 40m
Southwest
Mon 3/165:25 am
MDW
- GSP
1 stop5h 20m
Southwest
Deal found 2/9![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 2/10. 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 3/111:50 pm
GSP
- MDW
1 stop6h 45m
Southwest
Wed 3/183:35 pm
MDW
- GSP
1 stop6h 05m
Southwest
Deal found 2/10![Southwest logo]()
$229
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 February 11, 2026.
Search for one-way flight options from Greenville to Chicago. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 3/96:43 pm
GSP
- ORD
1 stop16h 53m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/115:43 pm
GSP
- ORD
1 stop28h 34m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 5/85:43 pm
GSP
- ORD
1 stop28h 34m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 4/245:43 pm
GSP
- ORD
1 stop28h 34m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 2/7. 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 4/76:45 am
GSP
- ORD
1 stop7h 05m
Southwest
Deal found 2/7![Southwest logo]()
$115
This Southwest deal was found by Cheapflights users on 2/10. 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 4/75:10 pm
GSP
- MDW
1 stop3h 50m
Southwest
Deal found 2/10![Southwest logo]()
$115
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/105:40 am
GSP
- ORD
1 stop3h 50m
Delta
Deal found 2/9![Delta logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Thu 3/52:12 pm
GSP
- ORD
1 stop6h 25m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$121
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:25 am
GSP
- MDW
1 stop9h 15m
Southwest
Deal found 2/10![Southwest logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 4/248:18 pm
GSP
- MDW
2 stops41h 42m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$145
This Delta deal was found by Cheapflights users on 2/8. 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.
Wed 5/2711:30 am
GSP
- MDW
1 stop5h 47m
Delta
Deal found 2/8![Delta logo]()
$154
This Southwest deal was found by Cheapflights users on 2/9. 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 2/2410:05 am
GSP
- MDW
1 stop5h 50m
Southwest
Deal found 2/9![Southwest logo]()
$157
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $147 (Delta) |
One-way from | $93 (Kiwi.com) |
Popular in | January |
Cheapest in | February |
Average price | $239 |
Good round-trip deal | $333 or less |
Good one-way deal | $210 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 February 11, 2026.
Use the filters below to find and compare flights from Greenville to Chicago that are best for you.
Fly from
Greenville
Fly to
Chicago
Route
Depart
Return
Price
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Sat 3/7
7:20 am-12:46 pm
1 stop6h 26m
Chicago Midway
Wed 3/11
6:07 pm-11:54 pm
1 stop4h 47m
$147
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Sat 3/21
7:40 am-8:56 am
Nonstop2h 16m
Chicago O'Hare Intl
Sat 3/28
7:22 pm-10:14 pm
Nonstop1h 52m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Wed 4/22
12:33 pm-1:50 pm
Nonstop2h 17m
Chicago O'Hare Intl
Sat 4/25
1:55 pm-4:54 pm
Nonstop1h 59m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Fri 3/6
8:21 pm-9:40 pm
Nonstop2h 19m
Chicago O'Hare Intl
Mon 3/9
8:00 am-10:56 am
Nonstop1h 56m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Thu 3/12
6:30 am-7:53 am
Nonstop2h 23m
Chicago O'Hare Intl
Sun 3/15
7:05 am-10:01 am
Nonstop1h 56m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Wed 4/22
12:33 pm-1:50 pm
Nonstop2h 17m
Chicago O'Hare Intl
Sun 4/26
8:40 am-11:44 am
Nonstop2h 04m
$209
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Fri 3/6
6:30 am-7:53 am
Nonstop2h 23m
Chicago O'Hare Intl
Sun 3/8
7:05 am-10:01 am
Nonstop1h 56m
$209
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Thu 4/23
5:21 pm-10:28 pm
1 stop6h 07m
Chicago Midway
Sun 4/26
6:00 am-12:21 pm
1 stop5h 21m
$213
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Thu 5/21
7:20 am-12:42 pm
1 stop6h 22m
Chicago Midway
Tue 5/26
6:30 am-12:03 pm
1 stop4h 33m
$213
GreenvilleChicago
GSP - ORD
GSPORD
Greenville
Thu 2/26
6:00 am-10:45 am
1 stop5h 45m
Chicago O'Hare Intl
Sat 3/7
10:35 am-5:44 pm
1 stop6h 09m
$218
Showing 1-10 of 38 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on 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
How far ahead should I book a flight from Greenville to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Greenville to Chicago. Price data was last updated on February 6, 2026.
To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 60 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 month to book a flight from Greenville to Chicago?
Currently, January is the cheapest month in which you can book a flight from Greenville to Chicago (average of $58). Flying from Greenville to Chicago in April is currently the most expensive (average of $124). 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 February 11, 2026.
It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 61% on the flight price compared to flying at noon, which is usually more expensive.
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 February 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.
How much does it cost to fly round-trip from Greenville to Chicago?
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 February 11, 2026.
Read through reviews of airlines operating flights from Greenville to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 11, 2026.
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Greenville and Chicago flights
Browse other Greenville and Chicago flight options. Last updated on February 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 February 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$107 | Average$279 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$199 | Average$293 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$319 | FlexibilityNo cancel fee | On-time69% |