$111+ Cheap flights from Durham, NC 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Dec 14 — Dec 211
Round-trip
1 adult, Economy
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Find cheap flights from Durham 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 Durham to Chicago are usually found in December or April, booked 76 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Durham to Chicago
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Cheapest flights from Durham to ChicagoExplore the most affordable flight options available from Durham to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2026.
Explore the most affordable flight options available from Durham to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:44 pm -
1 stop20h 16m
Thu 12/108:30 am -
2 stops11h 32m
Deal found 11/11![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:24 pm -
1 stop4h 43m
Mon 12/75:02 pm -
2 stops27h 00m
Deal found 11/11![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/229:52 pm -
1 stop28h 16m
Sat 12/264:45 pm -
1 stop6h 21m
Deal found 11/11![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Fri 12/412:24 pm -
1 stop6h 39m
Sat 12/124:00 pm -
1 stop6h 59m
Deal found 11/13![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 11/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:21 pm -
1 stop10h 39m
Sat 1/25:58 am -
1 stop7h 46m
Deal found 11/13![Frontier logo]()
$259
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:55 pm -
1 stop5h 30m
Sat 12/1910:50 am -
Nonstop1h 50m
Deal found 11/12![Southwest logo]()
$259
This Cheapflightsfares deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:19 pm -
1 stop23h 33m
Tue 12/295:47 pm -
1 stop20h 07m
Deal found 11/9![Frontier logo]()
$260
This Mytrip deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:59 am -
1 stop5h 34m
Wed 12/910:40 am -
2 stops12h 19m
Deal found 11/10![Frontier logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:34 pm -
1 stop10h 00m
Sun 12/65:24 pm -
1 stop23h 26m
Deal found 11/10![Frontier logo]()
$261
This Super.com deal was found by Cheapflights users on 11/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:09 am -
1 stop5h 24m
Fri 12/45:02 pm -
1 stop5h 55m
Deal found 11/13![Frontier logo]()
$261
This CheapOair deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:20 pm -
1 stop20h 10m
Tue 12/84:00 pm -
1 stop6h 59m
Deal found 11/11![Multiple Airlines logo]()
$262
This Justfly.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:09 am -
1 stop5h 24m
Tue 12/112:33 pm -
1 stop10h 24m
Deal found 11/11![Frontier logo]()
$262
Best flights from Durham to ChicagoDiscover carefully curated flight deals from Durham to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 14, 2026.
Discover carefully curated flight deals from Durham to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 14, 2026.
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:55 am -
Nonstop2h 29m
Fri 12/118:52 am -
1 stop4h 08m
Deal found 11/9![United Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:50 pm -
Nonstop2h 00m
Fri 12/47:05 am -
1 stop8h 40m
Deal found 11/9![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 11/12. 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.
Tue 12/85:07 am -
1 stop6h 21m
Tue 12/86:41 pm -
1 stop4h 03m
Deal found 11/12![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 11/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/128:05 am -
Nonstop2h 25m
Mon 12/148:45 am -
1 stop4h 15m
Deal found 11/12![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/71:50 pm -
Nonstop2h 00m
Wed 12/98:00 am -
1 stop3h 45m
Deal found 11/12![Southwest logo]()
$279
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/178:00 am -
Nonstop2h 34m
Fri 12/1810:25 am -
Nonstop2h 10m
Deal found 11/9![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/206:30 am -
1 stop7h 10m
Thu 1/215:30 pm -
Nonstop2h 00m
Deal found 11/10![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:30 am -
1 stop5h 19m
Thu 1/77:10 am -
1 stop4h 36m
Deal found 11/10![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/288:05 am -
Nonstop2h 00m
Mon 2/110:40 am -
1 stop6h 15m
Deal found 11/9![Southwest logo]()
$279
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:05 am -
Nonstop2h 25m
Thu 12/108:45 am -
1 stop4h 15m
Deal found 11/11![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/18:05 am -
Nonstop2h 05m
Mon 1/47:45 am -
Nonstop1h 55m
Deal found 11/9![Southwest logo]()
$279
This United Airlines deal was found by Cheapflights users on 11/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:05 am -
Nonstop2h 25m
Mon 12/142:25 pm -
Nonstop2h 14m
Deal found 11/12![United Airlines logo]()
$304
This KAYAK deal was found by Cheapflights users on 11/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:30 am -
1 stop6h 19m
Thu 12/176:49 am -
1 stop4h 54m
Deal found 11/13![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:05 am -
Nonstop2h 05m
Fri 12/116:30 pm -
1 stop4h 05m
Deal found 11/10![Southwest logo]()
$294
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1210:30 am -
1 stop7h 22m
Mon 2/152:33 pm -
Nonstop2h 07m
Deal found 11/11![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 11/12. 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 12/1012:56 pm -
1 stop4h 21m
Sun 12/136:49 am -
1 stop4h 54m
Deal found 11/12![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/51:50 pm -
Nonstop2h 00m
Thu 1/78:15 am -
Nonstop2h 00m
Deal found 11/13![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:15 am -
Nonstop2h 26m
Wed 12/28:52 am -
1 stop4h 08m
Deal found 11/11![United Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 11/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/228:03 pm -
1 stop4h 58m
Thu 12/316:44 am -
Nonstop2h 12m
Deal found 11/12![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 11/13. 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.
Sun 12/68:05 am -
Nonstop2h 25m
Wed 12/98:52 am -
1 stop4h 08m
Deal found 11/13![United Airlines logo]()
$386
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated November 14, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated November 14, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:09 am -
1 stop7h 42m
Tue 12/13:55 pm -
2 stops28h 06m
Deal found 11/11![Frontier logo]()
$262
This Justfly.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:09 am -
1 stop5h 24m
Tue 12/112:33 pm -
1 stop10h 24m
Deal found 11/11![Frontier logo]()
$262
This Super.com deal was found by Cheapflights users on 11/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:09 am -
1 stop5h 24m
Fri 12/45:02 pm -
1 stop5h 55m
Deal found 11/13![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:44 pm -
1 stop20h 16m
Thu 12/108:30 am -
2 stops11h 32m
Deal found 11/11![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:34 pm -
1 stop10h 00m
Sun 12/65:24 pm -
1 stop23h 26m
Deal found 11/10![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:24 pm -
1 stop4h 43m
Mon 12/75:02 pm -
2 stops27h 00m
Deal found 11/11![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Fri 12/412:24 pm -
1 stop6h 39m
Sat 12/124:00 pm -
1 stop6h 59m
Deal found 11/13![Frontier logo]()
$258
This Mytrip deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:59 am -
1 stop5h 34m
Wed 12/910:40 am -
2 stops12h 19m
Deal found 11/10![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 11/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:21 pm -
1 stop10h 39m
Sat 1/25:58 am -
1 stop7h 46m
Deal found 11/13![Frontier logo]()
$259
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:55 am -
Nonstop2h 29m
Thu 12/108:45 am -
1 stop4h 15m
Deal found 11/9![United Airlines logo]()
$260
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/124:20 pm -
Nonstop2h 05m
Tue 12/153:50 pm -
1 stop4h 10m
Deal found 11/12![Southwest logo]()
$259
This Cheapflightsfares deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/229:52 pm -
1 stop28h 16m
Sat 12/264:45 pm -
1 stop6h 21m
Deal found 11/11![Frontier logo]()
$257
One-way flights from Durham to ChicagoSearch for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated November 14, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated November 14, 2026.
This CheapOair deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/233:34 pm -
1 stop9h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/116:59 am -
1 stop29h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:44 pm -
2 stops17h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Frontier logo]()
$114
This Mytrip deal was found by Cheapflights users on 11/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:09 pm -
1 stop7h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Avelo Airlines logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:24 pm -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1312:21 pm -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 11/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:45 pm -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 11/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:24 pm -
1 stop4h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$119
This American Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/93:40 pm -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$120
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/91:50 pm -
Nonstop2h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$120
This Mytrip deal was found by Cheapflights users on 11/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:44 pm -
2 stops20h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:09 am -
1 stop9h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Frontier logo]()
$122
Find flight deals from Durham to Chicago
Keep the following information in mind while searching for Durham to Chicago flight deals. Data was last updated November 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $256 (Kiwi.com) |
One-way from | $111 (CheapOair) |
Popular in | July |
Cheapest in | December |
Average price | $337 |
Cheapflights Fare Finder
Customize your flight search to find flights from Durham 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 November 14, 2026.
Use the filters below to find and compare flights from Durham to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 1/13
3:33 pm-4:59 pm
Nonstop2h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$120
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Tue 12/22
8:00 am-9:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$120
Quickest round-trip
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Wed 12/9
1:50 pm-2:50 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$120
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 12/16
9:55 am-11:24 am
Nonstop2h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$120
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Tue 12/15
8:05 am-9:30 am
Nonstop2h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$125
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 12/31
8:05 am-9:10 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 12/22
5:25 am-12:00 pm
2 stops7h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Mon 12/28
6:59 am-12:00 pm
1 stop6h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Thu 12/31
3:59 pm-11:06 pm
1 stop8h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 12/7
12:21 pm-4:06 pm
1 stop4h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$145
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Durham to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Durham with our price prediction graph.
RDU-ORD
RDU-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 Durham to Chicago
DU8-CHI
RDU-ORD
RDU-MDW
What is the cheapest time of day to fly from DU8 to CHI?
Find hourly flight availability from Durham 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 November 14, 2026.
One of the essential ways to save on airfare from Durham to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 18% on airfare.
Weekly flight availability from Durham to Chicago
Explore weekly flight availability from Durham 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 November 14, 2026.
The most flights from DU8 to CHI are scheduled on a Friday (39 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (12 on average).
How much does it cost to fly round-trip from Durham to Chicago?
Airfare is below average for this route at the moment.
Durham to Chicago flights typically cost between $271 and $446 in December.The cheapest round-trip price found within the last 5 days was $256 on Frontier (Dec 3-Dec 10).
What is the cheapest day to fly from Durham to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Durham to Chicago. Price data was last updated on November 14, 2026.
Travelers seeking maximum savings on their Durham to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 November 14, 2026.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Durham 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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Alternative routes for Durham 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 November 14, 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 Durham to Chicago by cabin class
Find flights from Durham to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Durham and Chicago flights
Browse other Durham and Chicago flight options. Last updated on November 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Durham to Chicago flights
Consider these flights traveling from Durham to Chicago.
Top 6 airlines flying from Durham to Chicago
Discover the top 6 airlines that operate flights from Durham 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 November 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$380 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$331 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$209 | Average$360 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$420 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$379 | FlexibilityNo cancel fee | On-time63% |