$152+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — CHI
Nov 22 — Nov 291
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 February or January, booked 80 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Greensboro to Chicago
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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 October 23, 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 October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/186:18 pm -
1 stop29h 31m
Mon 12/216:08 am -
1 stop10h 20m
Deal found 10/20![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/75:54 pm -
2 stops18h 39m
Thu 12/108:37 pm -
1 stop14h 31m
Deal found 10/20![Multiple Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/307:34 am -
Nonstop2h 31m
Wed 1/63:00 pm -
Nonstop2h 06m
Deal found 10/19![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/217:34 am -
Nonstop2h 31m
Mon 11/238:05 am -
Nonstop2h 07m
Deal found 10/20![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/2111:42 am -
Nonstop2h 28m
Sun 11/227:15 pm -
Nonstop2h 06m
Deal found 10/21![American Airlines logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/136:15 am -
Nonstop2h 28m
Sat 11/142:05 pm -
Nonstop1h 57m
Deal found 10/23![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 11/1611:38 am -
Nonstop2h 27m
Mon 11/238:05 am -
Nonstop2h 07m
Deal found 10/19![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/17:00 am -
1 stop6h 04m
Sat 12/511:28 am -
1 stop6h 04m
Deal found 10/20![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/137:33 am -
Nonstop2h 32m
Mon 11/161:22 pm -
1 stop4h 30m
Deal found 10/21![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/216:00 am -
1 stop4h 46m
Sun 11/226:00 am -
1 stop4h 47m
Deal found 10/21![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/216:00 am -
1 stop5h 38m
Sun 11/222:44 pm -
1 stop6h 57m
Deal found 10/21![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 12/285:25 pm -
Nonstop2h 35m
Sat 1/28:52 am -
1 stop4h 32m
Deal found 10/19![United Airlines logo]()
$355
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 October 23, 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 October 23, 2026.
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 11/117:00 am -
1 stop4h 24m
Wed 11/186:00 am -
1 stop6h 58m
Deal found 10/19![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/316:00 am -
1 stop6h 37m
Sat 1/28:52 am -
1 stop4h 32m
Deal found 10/23![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/246:00 am -
1 stop4h 46m
Mon 11/3011:27 am -
1 stop5h 46m
Deal found 10/21![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/253:05 pm -
1 stop4h 45m
Thu 12/317:04 am -
1 stop6h 20m
Deal found 10/22![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/19. 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.
Sat 2/131:15 pm -
1 stop4h 10m
Mon 2/155:25 pm -
1 stop5h 29m
Deal found 10/19![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 2/156:00 am -
1 stop4h 41m
Sun 2/218:55 am -
1 stop4h 11m
Deal found 10/19![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/19. 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.
Sat 12/267:59 pm -
1 stop5h 00m
Fri 1/17:00 am -
1 stop3h 48m
Deal found 10/19![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/116:00 am -
1 stop6h 38m
Tue 11/176:20 pm -
Nonstop2h 12m
Deal found 10/23![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/118:17 am -
1 stop4h 42m
Tue 11/1711:27 am -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 10/19. 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.
Mon 11/162:43 pm -
1 stop5h 22m
Mon 11/235:05 pm -
1 stop4h 36m
Deal found 10/19![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 12/285:25 pm -
Nonstop2h 35m
Fri 1/11:45 pm -
Nonstop2h 03m
Deal found 10/19![United Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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
Wed 12/911:28 am -
1 stop6h 04m
Deal found 10/22![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/256:15 am -
Nonstop2h 28m
Mon 11/308:50 am -
1 stop4h 29m
Deal found 10/22![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/35:01 pm -
1 stop6h 53m
Sat 12/511:28 am -
1 stop6h 04m
Deal found 10/22![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/36:00 am -
1 stop4h 37m
Wed 12/91:02 pm -
1 stop4h 30m
Deal found 10/22![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/115:20 am -
1 stop6h 08m
Sat 12/126:00 am -
1 stop7h 02m
Deal found 10/22![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/35:20 am -
1 stop4h 29m
Tue 12/810:36 am -
1 stop4h 20m
Deal found 10/22![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/134:59 pm -
1 stop6h 55m
Sat 11/1411:27 am -
1 stop5h 57m
Deal found 10/23![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/2611:40 am -
1 stop4h 35m
Mon 11/305:13 pm -
1 stop3h 57m
Deal found 10/23![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/65:00 pm -
1 stop4h 38m
Tue 11/1010:32 am -
1 stop6h 52m
Deal found 10/20![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/266:00 am -
1 stop5h 38m
Mon 11/308:04 am -
1 stop6h 50m
Deal found 10/22![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/65:00 pm -
1 stop6h 33m
Mon 11/95:13 pm -
1 stop3h 57m
Deal found 10/20![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/2712:30 pm -
1 stop6h 14m
Wed 12/3012:55 pm -
1 stop5h 18m
Deal found 10/22![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/246:00 am -
1 stop5h 39m
Mon 11/306:15 pm -
1 stop4h 43m
Deal found 10/21![Delta logo]()
$439
Last-minute flights from Greensboro to ChicagoDiscover last-minute flight deals from Greensboro to Chicago. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Greensboro to Chicago. Data last updated October 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Tue 10/2711:40 am -
Nonstop2h 19m
Tue 11/103:04 pm -
Nonstop2h 00m
Deal found 10/19![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/118:17 am -
1 stop4h 42m
Tue 11/1711:27 am -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/136:15 am -
Nonstop2h 28m
Sat 11/142:05 pm -
Nonstop1h 57m
Deal found 10/23![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/137:33 am -
Nonstop2h 32m
Mon 11/161:22 pm -
1 stop4h 30m
Deal found 10/21![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/135:20 am -
1 stop6h 05m
Sun 11/155:30 am -
1 stop5h 17m
Deal found 10/21![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 11/1611:38 am -
Nonstop2h 27m
Mon 11/238:05 am -
Nonstop2h 07m
Deal found 10/19![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/217:34 am -
Nonstop2h 31m
Mon 11/238:05 am -
Nonstop2h 07m
Deal found 10/20![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/2111:42 am -
Nonstop2h 28m
Sun 11/227:15 pm -
Nonstop2h 06m
Deal found 10/21![American Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/216:00 am -
1 stop4h 46m
Sun 11/226:00 am -
1 stop4h 47m
Deal found 10/21![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/216:00 am -
1 stop5h 38m
Sun 11/222:44 pm -
1 stop6h 57m
Deal found 10/21![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/266:00 am -
1 stop5h 24m
Tue 12/111:28 am -
1 stop6h 04m
Deal found 10/23![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/286:15 am -
Nonstop2h 28m
Tue 12/18:52 am -
1 stop4h 28m
Deal found 10/21![United 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 October 23, 2026.
Search for one-way flight options from Greensboro to Chicago. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/115:54 pm -
2 stops29h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/115:54 pm -
2 stops18h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/207:00 pm -
2 stops29h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/207:00 pm -
2 stops38h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Wed 12/307:00 pm -
1 stop28h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/25:54 pm -
2 stops31h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 11/23:42 pm -
1 stop4h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Wed 12/307:00 pm -
2 stops30h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/2611:40 am -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/125:01 pm -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 -
2 stops24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 12/307:10 am -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$328
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 October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Kiwi.com) |
One-way from | $152 (Kiwi.com) |
Popular in | September |
Cheapest in | February |
Average price | $383 |
Good round-trip deal | $388 or less |
Good one-way deal | $283 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 October 23, 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
Fri 12/11
5:54 pm-11:33 am
2 stops18h 39m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Mon 11/2
3:42 pm-7:36 pm
1 stop4h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Wed 10/28
7:41 pm-9:13 pm
Nonstop2h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
Quickest round-trip
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Sun 11/29
6:15 am-7:43 am
Nonstop2h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Mon 12/28
5:25 pm-7:00 pm
Nonstop2h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Fri 12/11
12:33 pm-4:16 pm
1 stop4h 43m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Fri 1/1
4:58 pm-10:22 pm
1 stop6h 24m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
GreensboroChicago
GSO Greensboro/H. Point - MDW Chicago Midway
GSOMDW
Greensboro/H. Point
Thu 11/26
11:40 am-3:15 pm
1 stop4h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Tue 12/29
3:05 pm-6:50 pm
1 stop4h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
GreensboroChicago
GSO Greensboro/H. Point - ORD Chicago O'Hare Intl
GSOORD
Greensboro/H. Point
Thu 11/19
12:01 pm-4:18 pm
1 stop5h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
Showing 1-10 of 43 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 October.
| 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, January is the cheapest month in which you can book a flight from Greensboro to Chicago (average of $279). Flying from Greensboro to Chicago in September is currently the most expensive (average of $405). 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 October 23, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 25% 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 October 23, 2026.
The most flights from GSO to CHI are scheduled on a Wednesday (20 on average). You will have fewer flight options on Monday, 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 $292 and $437 in January.The cheapest round-trip price found within the last 5 days was $305 on Multiple Airlines (Jan 11-Jan 17).
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 October 17, 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 October 23, 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.
Crew
8.1
Entertainment
7.1
Overall
7.3
Food
6.7
Comfort
7.3
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Entertainment
7.1
Overall
7.3
Food
6.7
Comfort
7.3
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Entertainment
7.1
Overall
7.3
Food
6.7
Comfort
7.3
Boarding
7.7
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Greensboro and Chicago flights
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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 7,457,451 searches. Data last updated October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$354 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$326 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$262 | Average$328 | FlexibilityNo cancel fee | On-timeN/A |