$114+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Oct 16 — Oct 231
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 October, 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 September 16, 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 September 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Wed 10/2110:07 am -
2 stops9h 24m
Fri 10/237:44 pm -
1 stop18h 13m
Deal found 9/11![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/81:23 pm -
1 stop11h 20m
Sun 10/116:24 am -
1 stop15h 24m
Deal found 9/11![Frontier logo]()
$239
This FlightHub deal was found by Cheapflights users on 9/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:30 am -
1 stop7h 21m
Sun 11/89:51 am -
1 stop22h 26m
Deal found 9/11![Frontier logo]()
$241
This CheapOair deal was found by Cheapflights users on 9/11. 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 9/295:27 pm -
1 stop6h 32m
Tue 10/66:20 am -
1 stop5h 18m
Deal found 9/11![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/291:19 pm -
1 stop5h 28m
Thu 11/56:16 am -
1 stop5h 08m
Deal found 9/14![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/11:56 pm -
1 stop5h 27m
Mon 10/510:26 am -
1 stop13h 03m
Deal found 9/11![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/221:16 pm -
1 stop5h 29m
Wed 10/286:16 am -
1 stop8h 07m
Deal found 9/13![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/2110:07 am -
2 stops9h 24m
Mon 10/267:44 pm -
1 stop18h 39m
Deal found 9/14![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/161:16 pm -
1 stop11h 27m
Mon 10/196:15 am -
1 stop5h 06m
Deal found 9/12![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:16 pm -
1 stop6h 15m
Fri 10/164:41 pm -
1 stop15h 29m
Deal found 9/15![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 10/246:30 am -
1 stop6h 02m
Thu 10/2910:26 am -
2 stops11h 14m
Deal found 9/14![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/21:56 pm -
1 stop10h 48m
Mon 10/56:50 am -
1 stop4h 48m
Deal found 9/13![Frontier logo]()
$247
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 September 16, 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 September 16, 2026.
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:20 am -
1 stop4h 43m
Sat 10/179:29 am -
1 stop5h 32m
Deal found 9/15![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:20 am -
Nonstop2h 00m
Mon 10/263:45 pm -
1 stop6h 55m
Deal found 9/15![Southwest logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Sat 10/31:14 pm -
1 stop22h 08m
Mon 10/510:44 am -
1 stop21h 25m
Deal found 9/12![Multiple Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:50 am -
1 stop6h 04m
Fri 11/62:30 pm -
Nonstop2h 11m
Deal found 9/15![United Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:30 pm -
1 stop11h 24m
Mon 11/210:44 am -
1 stop21h 33m
Deal found 9/15![Multiple Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:10 pm -
1 stop6h 15m
Tue 10/203:05 pm -
2 stops6h 20m
Deal found 9/15![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:20 pm -
Nonstop2h 00m
Sat 10/178:20 am -
Nonstop2h 00m
Deal found 9/14![Southwest logo]()
$280
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:01 pm -
Nonstop2h 29m
Sat 10/1710:33 am -
Nonstop2h 16m
Deal found 9/15![United Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Tue 10/135:26 pm -
1 stop16h 18m
Fri 10/168:49 am -
1 stop23h 16m
Deal found 9/13![Multiple Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:50 am -
1 stop6h 04m
Sat 11/212:30 pm -
Nonstop2h 11m
Deal found 9/15![United Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/229:27 pm -
1 stop11h 27m
Wed 10/289:34 am -
1 stop22h 46m
Deal found 9/13![Multiple Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:50 am -
1 stop6h 04m
Sun 11/2210:37 am -
Nonstop2h 09m
Deal found 9/15![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:45 pm -
Nonstop2h 05m
Mon 11/97:45 am -
Nonstop1h 55m
Deal found 9/11![Southwest logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Thu 11/59:30 pm -
1 stop12h 08m
Sun 11/811:30 am -
1 stop20h 33m
Deal found 9/12![Multiple Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:50 am -
1 stop6h 09m
Sun 11/16:25 pm -
Nonstop2h 14m
Deal found 9/15![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:55 am -
Nonstop2h 00m
Wed 10/212:45 pm -
1 stop5h 40m
Deal found 9/11![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:45 pm -
1 stop4h 10m
Sun 11/16:45 pm -
Nonstop1h 50m
Deal found 9/15![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:13 am -
Nonstop2h 24m
Sat 10/178:50 am -
1 stop4h 15m
Deal found 9/15![United Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Wed 10/71:14 pm -
1 stop21h 37m
Sun 10/1110:30 am -
1 stop26h 29m
Deal found 9/13![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 11/19:46 pm -
1 stop20h 19m
Sun 11/810:30 am -
2 stops24h 33m
Deal found 9/13![Multiple Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:10 pm -
1 stop6h 15m
Sun 10/188:55 pm -
Nonstop2h 00m
Deal found 9/15![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:10 pm -
Nonstop2h 31m
Mon 10/56:25 pm -
Nonstop2h 21m
Deal found 9/15![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 9/12. 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.
Wed 11/41:50 pm -
Nonstop2h 00m
Tue 11/108:15 am -
Nonstop1h 50m
Deal found 9/12![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:13 am -
Nonstop2h 24m
Sat 10/2410:33 am -
Nonstop2h 16m
Deal found 9/14![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:50 pm -
2 stops6h 50m
Fri 10/234:20 pm -
2 stops6h 35m
Deal found 9/11![Southwest logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:30 am -
Nonstop2h 31m
Thu 10/226:25 pm -
Nonstop2h 21m
Deal found 9/14![United Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Mon 10/198:06 am -
Nonstop2h 24m
Thu 10/226:25 pm -
Nonstop2h 21m
Deal found 9/12![United Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Thu 10/2210:13 am -
Nonstop2h 24m
Sun 10/259:05 am -
Nonstop2h 19m
Deal found 9/12![United Airlines logo]()
$387
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated September 16, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/11. 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 9/295:27 pm -
1 stop6h 32m
Tue 10/66:20 am -
1 stop5h 18m
Deal found 9/11![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/11:56 pm -
1 stop5h 27m
Mon 10/510:26 am -
1 stop13h 03m
Deal found 9/11![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/21:56 pm -
1 stop10h 48m
Mon 10/56:50 am -
1 stop4h 48m
Deal found 9/13![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/81:23 pm -
1 stop11h 20m
Sun 10/116:24 am -
1 stop15h 24m
Deal found 9/11![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:16 pm -
1 stop6h 15m
Fri 10/164:41 pm -
1 stop15h 29m
Deal found 9/15![Frontier logo]()
$246
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:05 am -
Nonstop2h 22m
Tue 10/209:05 am -
Nonstop2h 23m
Deal found 9/15![United Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/161:16 pm -
1 stop11h 27m
Mon 10/196:15 am -
1 stop5h 06m
Deal found 9/12![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/2110:07 am -
2 stops9h 24m
Mon 10/267:44 pm -
1 stop18h 39m
Deal found 9/14![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/221:16 pm -
1 stop5h 29m
Wed 10/286:16 am -
1 stop8h 07m
Deal found 9/13![Frontier logo]()
$244
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:25 pm -
Nonstop2h 29m
Mon 10/268:55 pm -
Nonstop2h 04m
Deal found 9/15![American Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:20 am -
Nonstop2h 00m
Mon 10/268:00 am -
Nonstop2h 00m
Deal found 9/14![Southwest logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/291:19 pm -
1 stop5h 28m
Thu 11/56:16 am -
1 stop5h 08m
Deal found 9/14![Frontier logo]()
$242
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 September 16, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Wed 12/94:05 pm -
1 stop29h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$114
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:26 pm -
1 stop21h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/57:43 pm -
2 stops20h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/3012:58 pm -
1 stop24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 9/13. 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 10/137:00 am -
Nonstop2h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/197:43 pm -
2 stops20h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$118
This Super.com deal was found by Cheapflights users on 9/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:30 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 9/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:56 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$121
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:21 pm -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:58 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 11/126:07 am -
1 stop13h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 12/114:05 pm -
1 stop5h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$124
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 September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $239 (Kiwi.com) |
One-way from | $114 (Kiwi.com) |
Popular in | July |
Cheapest in | December |
Average price | $324 |
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 September 16, 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
Sun 10/4
6:35 am-9:20 am
1 stop27h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Sat 12/12
5:07 am-10:29 am
1 stop6h 22m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 10/13
1:50 pm-7:40 pm
2 stops6h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Thu 10/15
8:25 pm-9:54 pm
Nonstop2h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Mon 10/26
3:39 pm-5:10 pm
Nonstop2h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 10/12
1:16 pm-11:43 pm
1 stop11h 27m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Wed 10/7
1:14 pm-9:51 am
1 stop21h 37m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Mon 10/12
8:20 pm-12:08 am
1 stop4h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Thu 10/15
9:27 pm-7:59 am
1 stop11h 32m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 10/21
10:17 am-11:41 am
Nonstop2h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$162
Showing 1-10 of 58 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-MDW
RDU-ORD
RDU-RFD
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-MDW
RDU-ORD
RDU-RFD
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 September 16, 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 22% 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 September 16, 2026.
The most flights from DU8 to CHI are scheduled on a Monday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 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 $267 and $415 in November.The cheapest round-trip price found within the last 5 days was $241 on Frontier (Nov 7-Nov 8).
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 September 12, 2026.
Travelers seeking maximum savings on their Durham to Chicago flight should consider departing on Friday 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 16, 2026.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
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
Lansing
Merrillville
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 September 16, 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 September 16, 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 September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$330 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$336 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$322 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$356 | FlexibilityNo cancel fee | On-time63% |