$113+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Sep 16 — Sep 231
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 February, booked 44 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap flight deals from Greensboro to Chicago
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Best
Last-minute
One-way
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 August 17, 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 August 17, 2026.
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/1411:40 am -
Nonstop2h 19m
Tue 10/203:50 pm -
Nonstop2h 11m
Deal found 8/13![American Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/15. 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 9/115:51 pm -
Nonstop2h 14m
Sun 9/136:56 am -
Nonstop2h 05m
Deal found 8/15![United Airlines logo]()
$274
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:30 am -
Nonstop2h 17m
Sun 10/186:55 am -
Nonstop2h 07m
Deal found 8/16![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/14. 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 10/147:00 am -
1 stop4h 03m
Tue 10/206:04 am -
1 stop7h 06m
Deal found 8/14![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/186:43 pm -
Nonstop2h 38m
Sun 9/205:18 am -
1 stop6h 05m
Deal found 8/13![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 8/17. 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 9/115:00 pm -
1 stop6h 44m
Mon 9/146:05 am -
1 stop6h 59m
Deal found 8/17![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am -
1 stop4h 38m
Mon 9/146:25 am -
1 stop6h 47m
Deal found 8/16![United Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:30 am -
Nonstop2h 17m
Sun 10/116:55 am -
Nonstop2h 06m
Deal found 8/16![United Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:30 am -
Nonstop2h 17m
Sun 10/116:55 am -
Nonstop2h 06m
Deal found 8/14![United Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 am -
1 stop5h 29m
Sat 9/54:39 pm -
1 stop6h 20m
Deal found 8/12![Delta logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 9/45:24 pm -
1 stop5h 33m
Sat 9/1910:30 am -
Nonstop2h 07m
Deal found 8/16![American Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 8/296:49 pm -
Nonstop2h 35m
Sat 9/54:53 pm -
1 stop4h 07m
Deal found 8/12![American Airlines logo]()
$309
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 August 17, 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 August 17, 2026.
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 9/225:30 am -
1 stop5h 19m
Tue 9/291:00 pm -
1 stop6h 57m
Deal found 8/17![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
1 stop6h 59m
Sat 9/2612:55 pm -
1 stop4h 39m
Deal found 8/17![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 8/17. 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.
Wed 10/1412:00 pm -
1 stop5h 14m
Tue 10/2010:59 am -
1 stop5h 55m
Deal found 8/17![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:00 am -
1 stop6h 48m
Sun 10/257:29 am -
Nonstop2h 02m
Deal found 8/14![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
1 stop4h 38m
Sun 9/276:55 am -
Nonstop2h 06m
Deal found 8/14![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 8/15. 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 9/115:00 pm -
1 stop6h 44m
Mon 9/141:00 pm -
1 stop3h 59m
Deal found 8/15![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 9/225:30 am -
1 stop5h 19m
Mon 9/281:00 pm -
1 stop3h 59m
Deal found 8/17![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:30 am -
Nonstop2h 17m
Sun 10/186:55 am -
Nonstop2h 07m
Deal found 8/16![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/27:04 pm -
1 stop4h 40m
Sun 10/46:05 am -
1 stop4h 33m
Deal found 8/12![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Thu 9/246:00 am -
1 stop6h 48m
Sun 9/276:55 am -
Nonstop2h 06m
Deal found 8/15![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 8/15. 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 9/116:00 am -
1 stop4h 38m
Sun 9/136:30 am -
1 stop6h 42m
Deal found 8/15![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/206:39 am -
1 stop4h 34m
Sat 8/221:50 pm -
1 stop6h 41m
Deal found 8/13![Delta logo]()
$388
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:04 pm -
1 stop4h 40m
Mon 9/216:05 am -
1 stop6h 59m
Deal found 8/13![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:51 pm -
Nonstop2h 14m
Sat 9/56:15 pm -
Nonstop2h 05m
Deal found 8/16![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 8/14. 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 9/412:27 pm -
1 stop4h 48m
Tue 9/86:05 am -
1 stop4h 33m
Deal found 8/14![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Sat 8/2210:40 am -
Nonstop2h 12m
Thu 8/276:15 pm -
Nonstop2h 05m
Deal found 8/15![United Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/206:08 am -
1 stop4h 09m
Sun 8/2310:54 am -
1 stop5h 52m
Deal found 8/13![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/202:50 pm -
1 stop4h 59m
Sun 8/235:30 am -
1 stop3h 55m
Deal found 8/13![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 8/16. 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 8/214:30 pm -
1 stop7h 06m
Mon 8/2412:46 pm -
1 stop4h 00m
Deal found 8/16![Delta logo]()
$434
Last-minute flights from Greensboro to ChicagoDiscover last-minute flight deals from Greensboro to Chicago. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Greensboro to Chicago. Data last updated August 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/17. 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 8/221:40 pm -
Nonstop2h 20m
Tue 8/258:04 pm -
Nonstop2h 05m
Deal found 8/17![American Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 8/14. 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 8/2212:34 pm -
1 stop6h 59m
Tue 8/2512:46 pm -
1 stop7h 08m
Deal found 8/14![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 8/252:50 pm -
1 stop7h 05m
Mon 8/315:30 am -
1 stop5h 04m
Deal found 8/17![Delta logo]()
$353
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/2610:40 am -
Nonstop2h 12m
Sat 8/296:15 pm -
Nonstop2h 05m
Deal found 8/13![United Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/2610:19 am -
1 stop6h 41m
Sat 8/293:18 pm -
Nonstop2h 01m
Deal found 8/13![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/265:03 pm -
1 stop6h 33m
Sat 8/296:11 am -
1 stop6h 18m
Deal found 8/13![Delta logo]()
$353
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/271:16 pm -
Nonstop2h 20m
Thu 9/38:04 pm -
Nonstop2h 05m
Deal found 8/13![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/271:16 pm -
Nonstop2h 20m
Sun 8/308:04 pm -
Nonstop2h 05m
Deal found 8/13![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/276:08 am -
1 stop4h 09m
Sun 8/306:05 am -
1 stop6h 48m
Deal found 8/13![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/276:00 am -
1 stop6h 53m
Sun 8/308:45 am -
1 stop4h 29m
Deal found 8/13![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:40 am -
Nonstop2h 17m
Mon 8/316:59 am -
Nonstop2h 05m
Deal found 8/16![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 8/277:49 am -
Nonstop2h 21m
Mon 8/315:05 am -
1 stop3h 46m
Deal found 8/14![American Airlines logo]()
$364
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 August 17, 2026.
Search for one-way flight options from Greensboro to Chicago. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 8/319:50 pm -
1 stop26h 18m
Deal found 8/13![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/710:39 am -
2 stops50h 12m
Deal found 8/12![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:54 pm -
2 stops26h 50m
Deal found 8/13![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/145:54 pm -
1 stop30h 05m
Deal found 8/12![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/115:54 pm -
1 stop30h 05m
Deal found 8/12![Multiple Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 am -
1 stop4h 44m
Deal found 8/13![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 8/16. 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.
Sat 9/55:03 pm -
1 stop6h 33m
Deal found 8/16![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 9/187:04 pm -
1 stop4h 40m
Deal found 8/13![Delta logo]()
$459
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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (American Airlines) |
One-way from | $113 (Kiwi.com) |
Popular in | July |
Cheapest in | November |
Average price | $347 |
Good round-trip deal | $335 or less |
Good one-way deal | $294 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 August 17, 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
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Tue 9/22
5:30 am-9:49 am
1 stop5h 19m
Chicago Midway
Tue 9/29
1:00 pm-8:57 pm
1 stop6h 57m
$289
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Tue 9/22
6:00 am-11:59 am
1 stop6h 59m
Chicago O'Hare Intl
Sat 9/26
12:55 pm-6:34 pm
1 stop4h 39m
$289
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Wed 10/14
12:00 pm-4:14 pm
1 stop5h 14m
Chicago Midway
Tue 10/20
10:59 am-5:54 pm
1 stop5h 55m
$289
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Fri 10/23
6:00 am-11:48 am
1 stop6h 48m
Chicago O'Hare Intl
Sun 10/25
7:29 am-10:31 am
Nonstop2h 02m
$289
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Fri 9/25
6:00 am-9:38 am
1 stop4h 38m
Chicago O'Hare Intl
Sun 9/27
6:55 am-10:01 am
Nonstop2h 06m
$289
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Fri 9/11
5:00 pm-10:44 pm
1 stop6h 44m
Chicago Midway
Mon 9/14
1:00 pm-5:59 pm
1 stop3h 59m
$294
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Tue 9/22
5:30 am-9:49 am
1 stop5h 19m
Chicago Midway
Mon 9/28
1:00 pm-5:59 pm
1 stop3h 59m
$294
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Tue 10/13
6:30 am-7:47 am
Nonstop2h 17m
Chicago O'Hare Intl
Sun 10/18
6:55 am-10:02 am
Nonstop2h 07m
$354
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Fri 10/2
7:04 pm-10:44 pm
1 stop4h 40m
Chicago Midway
Sun 10/4
6:05 am-11:38 am
1 stop4h 33m
$359
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Thu 9/24
6:00 am-11:48 am
1 stop6h 48m
Chicago O'Hare Intl
Sun 9/27
6:55 am-10:01 am
Nonstop2h 06m
$369
Showing 1-10 of 32 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 August.
| 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, November is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $267). Flying from Greensboro to Chicago in July is currently the most expensive (average of $370). 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 August 17, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 23% on flights from Greensboro to Chicago by exploring options for tickets in the evening.
Weekly flight availability from Greensboro to Chicago
Explore weekly flight availability from Greensboro 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 August 17, 2026.
The most flights from GSO to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Greensboro to Chicago?
Airfare is below average for this route at the moment.
Greensboro to Chicago flights typically cost between $305 and $462 in October.The cheapest round-trip price found within the last 5 days was $269 on American Airlines (Oct 14-Oct 20).
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 August 15, 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 August 17, 2026.
Read reviews from past customers who have flown United Airlines and American 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.
Entertainment
7.1
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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
Valparaiso
Hammond
Saint Joseph
Porter
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Greensboro and Chicago flights
Browse other Greensboro and Chicago flight options. Last updated on August 17, 2026.
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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 August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$188 | Average$300 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$199 | Average$306 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$312 | FlexibilityNo cancel fee | On-time71% |