$158+ Cheap flights from Greensboro (GSO) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Oct 3 — Oct 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
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 September 3, 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 September 3, 2026.
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/2![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/15:51 pm -
Nonstop2h 14m
Sat 10/36:55 am -
Nonstop2h 06m
Deal found 9/3![United Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/157:41 pm -
Nonstop2h 32m
Mon 10/193:50 pm -
Nonstop2h 11m
Deal found 9/2![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/17:06 pm -
1 stop4h 25m
Sat 10/37:39 pm -
Nonstop2h 10m
Deal found 9/2![American Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/3![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/235:00 pm -
1 stop6h 44m
Wed 10/2812:49 pm -
1 stop4h 05m
Deal found 9/2![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/17:04 pm -
1 stop5h 55m
Sat 10/32:00 pm -
1 stop6h 39m
Deal found 9/3![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/266:00 am -
1 stop4h 07m
Mon 9/2810:48 am -
1 stop6h 11m
Deal found 8/30![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1512:00 pm -
1 stop5h 58m
Mon 10/198:05 am -
1 stop5h 05m
Deal found 9/2![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/136:56 am -
Nonstop2h 05m
Deal found 8/29![United Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/187:22 pm -
1 stop5h 14m
Tue 9/223:05 pm -
Nonstop2h 08m
Deal found 9/1![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:25 am -
Nonstop2h 24m
Tue 10/138:09 am -
Nonstop2h 01m
Deal found 9/1![American Airlines logo]()
$330
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 September 3, 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 September 3, 2026.
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/26:30 am -
Nonstop2h 17m
Sat 10/102:08 pm -
Nonstop2h 00m
Deal found 9/1![United Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/316:00 am -
1 stop4h 32m
Sat 11/76:04 am -
1 stop6h 08m
Deal found 9/1![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am -
1 stop4h 37m
Mon 12/75:14 pm -
1 stop3h 58m
Deal found 8/29![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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
Sat 10/176:08 pm -
Nonstop2h 05m
Deal found 9/3![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/247:04 pm -
1 stop4h 40m
Wed 9/301:00 pm -
1 stop3h 59m
Deal found 8/30![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/236:00 am -
1 stop6h 59m
Sun 9/278:50 am -
1 stop4h 24m
Deal found 9/2![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/261:00 pm -
1 stop6h 22m
Wed 9/301:00 pm -
1 stop3h 59m
Deal found 8/30![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/16:00 am -
1 stop4h 07m
Sat 11/74:19 pm -
1 stop6h 40m
Deal found 8/31![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/176:30 am -
Nonstop2h 17m
Sat 10/246:08 pm -
Nonstop2h 05m
Deal found 9/2![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/257:11 pm -
1 stop4h 33m
Sun 9/276:05 am -
1 stop4h 33m
Deal found 8/30![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/235:51 pm -
Nonstop2h 14m
Tue 9/296:08 pm -
Nonstop2h 05m
Deal found 8/30![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/167:00 pm -
1 stop4h 33m
Sun 10/186:04 am -
1 stop7h 06m
Deal found 8/29![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/295:51 pm -
Nonstop2h 14m
Sat 10/36:08 pm -
Nonstop2h 05m
Deal found 9/1![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/262:49 pm -
1 stop5h 07m
Mon 9/285:10 pm -
1 stop4h 22m
Deal found 8/30![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 stop4h 38m
Sun 9/278:50 am -
1 stop4h 24m
Deal found 8/30![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/67:07 am -
1 stop4h 03m
Tue 9/86:05 am -
1 stop4h 33m
Deal found 8/30![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/155:30 am -
1 stop5h 19m
Wed 9/236:05 am -
1 stop4h 33m
Deal found 9/2![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2110:48 am -
1 stop6h 11m
Deal found 8/31![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/2611:38 am -
1 stop4h 46m
Sun 9/276:05 am -
1 stop4h 33m
Deal found 9/2![Delta logo]()
$369
Last-minute flights from Greensboro to ChicagoDiscover last-minute flight deals from Greensboro to Chicago. Data last updated September 3, 2026 and is based on user searches.
Discover last-minute flight deals from Greensboro to Chicago. Data last updated September 3, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/136:56 am -
Nonstop2h 05m
Deal found 8/29![United Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/187:22 pm -
1 stop5h 14m
Tue 9/223:05 pm -
Nonstop2h 08m
Deal found 9/1![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/235:00 pm -
1 stop6h 44m
Wed 10/2812:49 pm -
1 stop4h 05m
Deal found 9/2![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/266:00 am -
1 stop4h 07m
Mon 9/2810:48 am -
1 stop6h 11m
Deal found 8/30![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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
Sat 10/176:08 pm -
Nonstop2h 05m
Deal found 9/3![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/2![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/3![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1511:40 am -
Nonstop2h 19m
Sun 10/187:26 pm -
Nonstop2h 09m
Deal found 9/2![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1511:40 am -
Nonstop2h 19m
Mon 10/196:40 pm -
1 stop4h 13m
Deal found 9/2![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1512:00 pm -
1 stop5h 58m
Mon 10/198:05 am -
1 stop5h 05m
Deal found 9/2![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/176:30 am -
Nonstop2h 17m
Sun 10/186:55 am -
Nonstop2h 07m
Deal found 9/1![United Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/177:26 pm -
1 stop5h 42m
Mon 10/198:09 am -
Nonstop2h 01m
Deal found 8/31![American Airlines logo]()
$304
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 September 3, 2026.
Search for one-way flight options from Greensboro to Chicago. Find affordable one-way fares based on user searches. Data last updated September 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 9/285:54 pm -
2 stops25h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/55:54 pm -
2 stops25h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/305:54 pm -
1 stop15h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/29![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/25:54 pm -
2 stops25h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/195:54 pm -
2 stops30h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 -
2 stops25h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/29![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/1611:44 am -
2 stops36h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/248:10 am -
1 stop4h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/30![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/194:59 pm -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/29![Delta logo]()
$299
This KAYAK deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:26 pm -
1 stop3h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:00 pm -
2 stops22h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$312
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/185:25 am -
1 stop5h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$319
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 September 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (American Airlines) |
One-way from | $158 (Kiwi.com) |
Popular in | July |
Cheapest in | November |
Average price | $319 |
Good round-trip deal | $343 or less |
Good one-way deal | $328 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 7,457,451 searches. Data last updated September 3, 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 - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Thu 9/17
7:20 am-8:45 am
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$262
Quickest round-trip
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Thu 10/1
10:45 am-11:54 am
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Fri 10/2
10:45 am-11:54 am
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Fri 12/4
5:32 pm-6:50 pm
Nonstop2h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Fri 10/30
5:40 pm-7:00 pm
Nonstop2h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Sat 10/3
5:51 pm-7:05 pm
Nonstop2h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Sun 10/4
6:30 am-7:47 am
Nonstop2h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Fri 9/25
5:51 pm-7:05 pm
Nonstop2h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Tue 11/17
8:10 am-11:59 am
1 stop4h 49m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Sun 10/4
6:00 am-9:07 am
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
Showing 1-10 of 39 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 September.
| 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 $273). 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 September 3, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 22% 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 September 3, 2026.
The most flights from GSO to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Greensboro to Chicago?
Airfare is typical for this route at the moment.
Greensboro to Chicago flights typically cost between $269 and $377 in October.The cheapest round-trip price found within the last 5 days was $289 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 29, 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 September 3, 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.
Comfort
7.3
Food
6.7
Overall
7.4
Boarding
7.7
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Overall
7.4
Boarding
7.7
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Overall
7.4
Boarding
7.7
Entertainment
7.1
Crew
8.1
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Greensboro
Popular flights
Alternative routes for Greensboro to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 3, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Greensboro to Chicago by cabin class
Find flights from Greensboro to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Greensboro and Chicago flights
Browse other Greensboro and Chicago flight options. Last updated on September 3, 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 September 3, 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 7,457,451 searches. Data last updated September 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$199 | Average$309 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$314 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$249 | Average$313 | FlexibilityNo cancel fee | On-timeN/A |