$137+ Cheap flights from Greensboro (GSO) 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Jun 18 — Jun 251
Round-trip
1 adult, Economy
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Find cheap flights from Greensboro 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 Greensboro/H. Point to Chicago are usually found in November or July, booked 70 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Greensboro to Chicago
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Best
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Cheapest flights from Greensboro to ChicagoExplore the most affordable flight options available from Greensboro to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.
Explore the most affordable flight options available from Greensboro to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:35 am
GSO
- ORD
Nonstop2h 17m
United Airlines
Sat 9/196:18 pm
ORD
- GSO
Nonstop2h 05m
United Airlines
Deal found 5/18![United Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/155:10 am
GSO
- ORD
1 stop6h 50m
American Airlines
Sat 7/189:30 am
ORD
- GSO
Nonstop2h 04m
American Airlines
Deal found 5/19![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/205:30 pm
GSO
- ORD
1 stop6h 49m
American Airlines
Mon 6/226:42 pm
ORD
- GSO
Nonstop2h 09m
American Airlines
Deal found 5/19![American Airlines logo]()
$273
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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
GSO
- ORD
1 stop6h 12m
American Airlines
Mon 7/66:40 pm
ORD
- GSO
Nonstop2h 07m
American Airlines
Deal found 5/19![American Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/156:36 pm
GSO
- MDW
1 stop4h 39m
Delta
Sat 7/186:00 am
MDW
- GSO
1 stop5h 22m
Delta
Deal found 5/14![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/155:25 am
GSO
- ORD
1 stop5h 45m
Delta
Sat 7/187:00 am
ORD
- GSO
1 stop4h 22m
Delta
Deal found 5/15![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:15 pm
GSO
- MDW
1 stop5h 30m
Delta
Sat 10/241:05 pm
MDW
- GSO
1 stop3h 52m
Delta
Deal found 5/14![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/158:14 am
GSO
- ORD
1 stop5h 20m
Delta
Sun 7/196:35 am
ORD
- GSO
1 stop6h 29m
Delta
Deal found 5/14![Delta logo]()
$284
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 9/1110:40 am
GSO
- ORD
Nonstop2h 12m
United Airlines
Sun 9/136:59 am
ORD
- GSO
Nonstop2h 05m
United Airlines
Deal found 5/19![United Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/246:36 pm
GSO
- MDW
1 stop4h 39m
Delta
Mon 7/276:00 am
MDW
- GSO
1 stop4h 34m
Delta
Deal found 5/15![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/125:25 am
GSO
- ORD
1 stop4h 13m
Delta
Fri 6/196:35 am
ORD
- GSO
1 stop6h 14m
Delta
Deal found 5/18![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 5/297:30 am
GSO
- ORD
Nonstop2h 23m
American Airlines
Mon 6/15:34 pm
ORD
- GSO
1 stop5h 24m
American Airlines
Deal found 5/17![American Airlines logo]()
$294
Best flights from Greensboro to ChicagoDiscover carefully curated flight deals from Greensboro to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 19, 2026.
Discover carefully curated flight deals from Greensboro to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 19, 2026.
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/181:04 pm
GSO
- ORD
Nonstop2h 15m
American Airlines
Mon 7/206:40 pm
ORD
- GSO
Nonstop2h 07m
American Airlines
Deal found 5/14![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/156:36 pm
GSO
- MDW
1 stop4h 39m
Delta
Sat 7/186:00 am
MDW
- GSO
1 stop5h 22m
Delta
Deal found 5/14![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 11/138:00 pm
GSO
- ORD
1 stop4h 15m
United Airlines
Mon 11/165:55 pm
ORD
- GSO
Nonstop2h 02m
United Airlines
Deal found 5/15![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/145:25 am
GSO
- MDW
1 stop5h 40m
Delta
Sat 7/186:00 am
MDW
- GSO
1 stop5h 22m
Delta
Deal found 5/19![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/96:15 am
GSO
- ORD
1 stop4h 21m
United Airlines
Sat 7/113:53 pm
ORD
- GSO
1 stop6h 43m
United Airlines
Deal found 5/18![United Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 5/297:31 pm
GSO
- ORD
Nonstop2h 34m
American Airlines
Tue 6/211:59 am
ORD
- GSO
1 stop4h 49m
American Airlines
Deal found 5/14![American Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/3010:14 am
GSO
- MDW
1 stop7h 01m
Delta
Sat 8/16:00 am
MDW
- GSO
1 stop5h 22m
Delta
Deal found 5/16![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/186:55 pm
GSO
- ORD
1 stop5h 58m
Delta
Mon 7/205:18 pm
ORD
- GSO
1 stop4h 00m
Delta
Deal found 5/14![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/187:59 pm
GSO
- ORD
1 stop5h 00m
Delta
Tue 6/239:48 am
ORD
- GSO
1 stop5h 02m
Delta
Deal found 5/16![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/135:30 am
GSO
- MDW
1 stop5h 29m
Delta
Mon 8/1710:54 am
MDW
- GSO
1 stop5h 52m
Delta
Deal found 5/14![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/246:36 pm
GSO
- MDW
1 stop4h 39m
Delta
Sun 7/266:00 am
MDW
- GSO
1 stop7h 04m
Delta
Deal found 5/15![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/96:44 pm
GSO
- MDW
1 stop4h 33m
Delta
Sat 6/1310:55 am
MDW
- GSO
1 stop3h 55m
Delta
Deal found 5/18![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/1410:11 am
GSO
- MDW
1 stop7h 04m
Delta
Sun 8/166:05 am
MDW
- GSO
1 stop6h 48m
Delta
Deal found 5/17![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/126:44 pm
GSO
- MDW
1 stop4h 33m
Delta
Fri 6/196:00 am
MDW
- GSO
1 stop6h 49m
Delta
Deal found 5/16![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:20 am
GSO
- ORD
1 stop4h 46m
Delta
Sun 10/187:10 am
ORD
- GSO
1 stop5h 36m
Delta
Deal found 5/17![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/172:54 pm
GSO
- ORD
1 stop6h 39m
Delta
Sun 7/196:35 am
ORD
- GSO
1 stop6h 29m
Delta
Deal found 5/18![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/147:51 am
GSO
- ORD
1 stop7h 14m
Delta
Sun 8/168:02 am
ORD
- GSO
1 stop4h 51m
Delta
Deal found 5/17![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/2011:22 am
GSO
- ORD
1 stop6h 02m
Delta
Sun 8/236:40 am
ORD
- GSO
1 stop6h 13m
Delta
Deal found 5/19![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/257:59 pm
GSO
- ORD
1 stop5h 00m
Delta
Mon 6/296:35 am
ORD
- GSO
1 stop6h 14m
Delta
Deal found 5/17![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/284:07 pm
GSO
- MDW
1 stop6h 02m
Delta
Wed 6/35:15 pm
MDW
- GSO
1 stop5h 42m
Delta
Deal found 5/18![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 5/294:07 pm
GSO
- MDW
1 stop6h 02m
Delta
Sun 5/316:23 am
MDW
- GSO
1 stop4h 53m
Delta
Deal found 5/15![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 5/2912:31 pm
GSO
- ORD
1 stop7h 04m
Delta
Tue 6/211:09 am
ORD
- GSO
1 stop5h 28m
Delta
Deal found 5/14![Delta logo]()
$304
Last-minute flights from Greensboro to ChicagoDiscover last-minute flight deals from Greensboro to Chicago. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from Greensboro to Chicago. Data last updated May 19, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/235:32 pm
GSO
- ORD
Nonstop2h 23m
United Airlines
Wed 7/16:15 pm
ORD
- GSO
Nonstop2h 08m
United Airlines
Deal found 5/18![United Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 5/297:30 am
GSO
- ORD
Nonstop2h 23m
American Airlines
Sun 5/318:48 am
ORD
- GSO
1 stop4h 10m
American Airlines
Deal found 5/17![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/67:28 pm
GSO
- ORD
Nonstop2h 31m
American Airlines
Fri 6/124:44 pm
ORD
- GSO
1 stop5h 11m
American Airlines
Deal found 5/17![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/127:33 pm
GSO
- ORD
Nonstop2h 31m
American Airlines
Wed 6/176:42 pm
ORD
- GSO
Nonstop2h 09m
American Airlines
Deal found 5/14![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/127:33 pm
GSO
- ORD
Nonstop2h 31m
American Airlines
Mon 6/156:42 pm
ORD
- GSO
Nonstop2h 09m
American Airlines
Deal found 5/19![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/126:44 pm
GSO
- MDW
1 stop4h 33m
Delta
Wed 6/1712:50 pm
MDW
- GSO
1 stop5h 21m
Delta
Deal found 5/14![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/126:44 pm
GSO
- MDW
1 stop4h 33m
Delta
Fri 6/196:00 am
MDW
- GSO
1 stop4h 38m
Delta
Deal found 5/18![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/125:25 am
GSO
- ORD
1 stop4h 13m
Delta
Fri 6/196:35 am
ORD
- GSO
1 stop6h 14m
Delta
Deal found 5/18![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/176:00 am
GSO
- MDW
1 stop4h 14m
Delta
Wed 6/246:00 am
MDW
- GSO
1 stop6h 49m
Delta
Deal found 5/18![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/187:48 pm
GSO
- ORD
1 stop5h 10m
American Airlines
Tue 6/2310:05 am
ORD
- GSO
Nonstop2h 09m
American Airlines
Deal found 5/19![American Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/187:59 pm
GSO
- ORD
1 stop5h 00m
Delta
Tue 6/2311:30 am
ORD
- GSO
1 stop5h 24m
Delta
Deal found 5/18![Delta logo]()
$284
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/205:30 pm
GSO
- ORD
1 stop6h 49m
American Airlines
Mon 6/226:42 pm
ORD
- GSO
Nonstop2h 09m
American Airlines
Deal found 5/19![American Airlines logo]()
$273
One-way flights from Greensboro to ChicagoSearch for one-way flight options from Greensboro to Chicago. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
Search for one-way flight options from Greensboro to Chicago. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/139:50 pm
GSO
- ORD
2 stops23h 03m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/89:36 pm
GSO
- ORD
2 stops28h 12m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/179:36 pm
GSO
- ORD
2 stops35h 27m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/159:36 pm
GSO
- ORD
2 stops23h 14m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/109:50 pm
GSO
- ORD
2 stops32h 38m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$174
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Mon 6/157:48 pm
GSO
- ORD
1 stop5h 10m
American Airlines
Deal found 5/16![American Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/159:36 pm
GSO
- MDW
2 stops25h 35m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/149:36 pm
GSO
- ORD
2 stops28h 13m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/129:36 pm
GSO
- MDW
2 stops41h 20m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 5/259:36 pm
GSO
- MDW
2 stops17h 36m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 5/299:36 pm
GSO
- MDW
2 stops25h 26m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/125:25 am
GSO
- MDW
1 stop5h 44m
Delta
Deal found 5/17![Delta logo]()
$264
Find flight deals from Greensboro to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Greensboro (GSO) 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 May 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $264 (United Airlines) |
One-way from | $137 (Kiwi.com) |
Popular in | April |
Cheapest in | November |
Average price | $279 |
Good round-trip deal | $357 or less |
Good one-way deal | $276 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Greensboro 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 May 19, 2026.
Use the filters below to find and compare flights from Greensboro to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
GreensboroChicago
GSO - ORD
GSOORD
Greensboro/H. Point
Sat 7/18
1:04 pm-2:19 pm
Nonstop2h 15m
Chicago O'Hare Intl
Mon 7/20
6:40 pm-9:47 pm
Nonstop2h 07m
$264
GreensboroChicago
GSO - MDW
GSOMDW
Greensboro/H. Point
Wed 7/15
6:36 pm-10:15 pm
1 stop4h 39m
Chicago Midway
Sat 7/18
6:00 am-12:22 pm
1 stop5h 22m
$279
GreensboroChicago
GSO - ORD
GSOORD
Greensboro/H. Point
Fri 11/13
8:00 pm-11:15 pm
1 stop4h 15m
Chicago O'Hare Intl
Mon 11/16
5:55 pm-8:57 pm
Nonstop2h 02m
$279
GreensboroChicago
GSO - MDW
GSOMDW
Greensboro/H. Point
Tue 7/14
5:25 am-10:05 am
1 stop5h 40m
Chicago Midway
Sat 7/18
6:00 am-12:22 pm
1 stop5h 22m
$279
GreensboroChicago
GSO - ORD
GSOORD
Greensboro/H. Point
Thu 7/9
6:15 am-9:36 am
1 stop4h 21m
Chicago O'Hare Intl
Sat 7/11
3:53 pm-11:36 pm
1 stop6h 43m
$284
GreensboroChicago
GSO - MDW
GSOMDW
Greensboro/H. Point
Thu 7/30
10:14 am-4:15 pm
1 stop7h 01m
Chicago Midway
Sat 8/1
6:00 am-12:22 pm
1 stop5h 22m
$284
GreensboroChicago
GSO - ORD
GSOORD
Greensboro/H. Point
Sat 7/18
6:55 pm-11:53 pm
1 stop5h 58m
Chicago O'Hare Intl
Mon 7/20
5:18 pm-10:18 pm
1 stop4h 00m
$284
GreensboroChicago
GSO - ORD
GSOORD
Greensboro/H. Point
Thu 6/18
7:59 pm-11:59 pm
1 stop5h 00m
Chicago O'Hare Intl
Tue 6/23
9:48 am-3:50 pm
1 stop5h 02m
$284
GreensboroChicago
GSO - MDW
GSOMDW
Greensboro/H. Point
Thu 8/13
5:30 am-9:59 am
1 stop5h 29m
Chicago Midway
Mon 8/17
10:54 am-5:46 pm
1 stop5h 52m
$289
GreensboroChicago
GSO - MDW
GSOMDW
Greensboro/H. Point
Fri 7/24
6:36 pm-10:15 pm
1 stop4h 39m
Chicago Midway
Sun 7/26
6:00 am-2:04 pm
1 stop7h 04m
$289
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Greensboro 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 Greensboro to Chicago in May.
| 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 Greensboro-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greensboro-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Greensboro-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Greensboro-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 Greensboro-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 Greensboro to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Greensboro with our price prediction graph.
GSO-CHI
GSO-ORD
GSO-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 Greensboro to Chicago
GSO-CHI
GSO-ORD
GSO-MDW
What is the cheapest month to book a flight from Greensboro to Chicago?
Currently, August is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $56). Flying from Greensboro to Chicago in March is currently the most expensive (average of $199). 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 GSO to CHI?
Find hourly flight availability from Greensboro 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 May 19, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 21% on flights from Greensboro to Chicago by exploring options for tickets in the evening.
How much does it cost to fly round-trip from Greensboro to Chicago?
How far ahead should I book a flight from Greensboro to Chicago?
The best time to book flights from Greensboro to Chicago is 69 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Greensboro to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Greensboro to Chicago. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Greensboro to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday 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 May 19, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Greensboro to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
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 Greensboro 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
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Porter
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Other flights to Chicago
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Greensboro and Chicago flights
Browse other Greensboro and Chicago flight options. Last updated on May 19, 2026.
Other flights from Greensboro
Browse through other flights departing from Greensboro. Flights are based on user searches made on Cheapflights and were last updated on May 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Greensboro to Chicago
Discover the top 3 airlines that operate flights from Greensboro 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 May 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$188 | Average$285 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$199 | Average$302 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$204 | Average$289 | FlexibilityNo cancel fee | On-time71% |