$109+ Cheap flights from Durham, NC to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Oct 2 — Oct 91
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 2, 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 2, 2026.
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:55 am -
1 stop8h 40m
Mon 9/283:50 pm -
1 stop16h 19m
Deal found 8/31![Frontier logo]()
$232
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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 10/63:50 pm -
1 stop16h 19m
Deal found 8/31![Frontier logo]()
$233
This deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:56 pm -
1 stop4h 55m
Fri 10/26:25 am -
1 stop5h 13m
Deal found 8/28![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 am -
1 stop6h 16m
Mon 9/283:50 pm -
1 stop23h 41m
Deal found 8/31![Frontier logo]()
$234
This FlightHub deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:35 am -
1 stop6h 16m
Fri 10/23:50 pm -
1 stop19h 54m
Deal found 9/2![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:56 pm -
1 stop4h 50m
Thu 9/246:46 pm -
1 stop4h 43m
Deal found 9/1![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/161:16 pm -
1 stop11h 27m
Mon 10/196:15 am -
1 stop5h 06m
Deal found 8/28![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:35 am -
1 stop27h 45m
Tue 9/297:28 pm -
1 stop16h 10m
Deal found 9/1![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:56 pm -
1 stop4h 50m
Mon 9/286:46 pm -
1 stop4h 43m
Deal found 8/31![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:35 am -
1 stop6h 16m
Mon 9/287:28 pm -
1 stop16h 10m
Deal found 9/1![Frontier logo]()
$238
This Expedia deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:46 pm -
1 stop26h 13m
Thu 9/2411:15 am -
1 stop21h 03m
Deal found 9/2![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:56 pm -
1 stop4h 50m
Sat 9/266:25 am -
1 stop5h 13m
Deal found 8/31![Frontier logo]()
$239
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 2, 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 2, 2026.
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/131:10 pm -
Nonstop2h 31m
Tue 10/209:05 am -
Nonstop2h 23m
Deal found 9/1![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:25 pm -
Nonstop1h 55m
Mon 10/56:50 pm -
Nonstop1h 55m
Deal found 9/1![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:35 am -
1 stop23h 43m
Thu 10/89:40 am -
1 stop27h 19m
Deal found 8/30![Multiple Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:40 am -
1 stop4h 33m
Thu 10/225:29 pm -
1 stop5h 12m
Deal found 8/29![Delta logo]()
$343
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am -
Nonstop2h 00m
Mon 10/196:50 pm -
Nonstop1h 55m
Deal found 9/1![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:05 am -
1 stop5h 55m
Sat 10/109:05 am -
Nonstop2h 23m
Deal found 9/1![United Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:20 pm -
2 stops17h 30m
Mon 10/1910:39 am -
1 stop21h 38m
Deal found 8/31![Multiple Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:55 am -
Nonstop2h 00m
Mon 10/264:30 pm -
1 stop5h 45m
Deal found 8/31![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:50 am -
1 stop6h 09m
Fri 11/67:30 am -
Nonstop2h 14m
Deal found 9/1![United Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:20 pm -
2 stops17h 20m
Fri 11/137:58 pm -
1 stop12h 01m
Deal found 9/2![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 11/910:38 am -
2 stops27h 45m
Deal found 8/31![Multiple Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:35 am -
2 stops7h 00m
Tue 11/310:20 am -
2 stops6h 25m
Deal found 9/1![Southwest logo]()
$298
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:05 am -
Nonstop2h 22m
Mon 10/126:25 pm -
Nonstop2h 21m
Deal found 9/1![United Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:26 pm -
1 stop16h 18m
Fri 10/167:56 pm -
1 stop12h 03m
Deal found 9/2![Multiple Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am -
Nonstop2h 00m
Sun 10/187:45 am -
Nonstop2h 00m
Deal found 9/1![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:05 am -
Nonstop2h 22m
Sat 10/177:25 am -
Nonstop2h 23m
Deal found 8/29![United Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:27 pm -
1 stop11h 32m
Mon 10/1910:39 am -
1 stop21h 38m
Deal found 8/29![Multiple Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:45 pm -
Nonstop1h 55m
Fri 9/256:30 pm -
Nonstop2h 00m
Deal found 8/29![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:05 am -
1 stop5h 55m
Wed 10/79:05 am -
Nonstop2h 23m
Deal found 8/29![United Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:30 pm -
1 stop13h 24m
Sun 11/810:30 am -
1 stop26h 28m
Deal found 9/1![Multiple Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am -
1 stop4h 38m
Mon 9/212:07 pm -
Nonstop2h 11m
Deal found 8/29![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:15 pm -
Nonstop1h 50m
Wed 9/3011:10 am -
1 stop7h 00m
Deal found 8/30![Southwest logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:46 pm -
1 stop22h 20m
Mon 10/265:55 pm -
1 stop15h 04m
Deal found 8/31![Multiple Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:05 am -
Nonstop2h 27m
Tue 12/18:55 am -
1 stop3h 54m
Deal found 8/30![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:00 am -
Nonstop2h 00m
Sun 10/118:55 pm -
Nonstop2h 00m
Deal found 8/31![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:15 am -
Nonstop2h 26m
Sat 11/282:30 pm -
Nonstop2h 11m
Deal found 8/30![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:55 pm -
2 stops7h 10m
Sun 11/156:10 pm -
1 stop4h 30m
Deal found 9/1![Southwest logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:35 pm -
1 stop12h 17m
Mon 9/288:44 pm -
2 stops23h 33m
Deal found 8/30![Multiple Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:20 am -
2 stops7h 35m
Wed 10/71:35 pm -
2 stops5h 25m
Deal found 8/29![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:45 pm -
1 stop4h 47m
Sun 10/1810:33 am -
Nonstop2h 16m
Deal found 8/29![United Airlines logo]()
$355
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated September 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:56 pm -
1 stop4h 50m
Thu 9/246:46 pm -
1 stop4h 43m
Deal found 9/1![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:56 pm -
1 stop4h 50m
Mon 9/286:46 pm -
1 stop4h 43m
Deal found 8/31![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:56 pm -
1 stop4h 50m
Sat 9/266:25 am -
1 stop5h 13m
Deal found 8/31![Frontier logo]()
$239
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:55 am -
1 stop8h 40m
Mon 9/283:50 pm -
1 stop16h 19m
Deal found 8/31![Frontier logo]()
$232
This Expedia deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:46 pm -
1 stop26h 13m
Thu 9/2411:15 am -
1 stop21h 03m
Deal found 9/2![Frontier logo]()
$239
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 am -
1 stop6h 16m
Mon 9/283:50 pm -
1 stop23h 41m
Deal found 8/31![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:35 am -
1 stop6h 16m
Mon 9/287:28 pm -
1 stop16h 10m
Deal found 9/1![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:35 am -
1 stop27h 45m
Tue 9/297:28 pm -
1 stop16h 10m
Deal found 9/1![Frontier logo]()
$237
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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 10/63:50 pm -
1 stop16h 19m
Deal found 8/31![Frontier logo]()
$233
This deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:56 pm -
1 stop4h 55m
Fri 10/26:25 am -
1 stop5h 13m
Deal found 8/28![Frontier logo]()
$233
This FlightHub deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:35 am -
1 stop6h 16m
Fri 10/23:50 pm -
1 stop19h 54m
Deal found 9/2![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:56 pm -
1 stop5h 27m
Sun 10/1110:26 am -
1 stop11h 22m
Deal found 9/2![Frontier logo]()
$240
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 2, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:19 pm -
1 stop6h 26m
Deal found 9/1![Frontier logo]()
$109
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 am -
1 stop12h 58m
Deal found 9/1![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:56 pm -
1 stop4h 55m
Deal found 8/31![Frontier logo]()
$110
This Priceline deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:30 am -
1 stop6h 00m
Deal found 9/2![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 am -
1 stop12h 26m
Deal found 9/1![Frontier logo]()
$111
This Priceline deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:58 pm -
1 stop6h 47m
Deal found 9/1![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:56 pm -
1 stop5h 27m
Deal found 8/30![Frontier logo]()
$113
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:56 pm -
1 stop4h 50m
Deal found 8/31![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:56 pm -
1 stop4h 50m
Deal found 8/29![Frontier logo]()
$114
This Orbitz deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:26 pm -
1 stop21h 59m
Deal found 9/2![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:55 pm -
1 stop8h 48m
Deal found 9/1![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:26 pm -
1 stop11h 57m
Deal found 8/30![Frontier logo]()
$116
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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $232 (CheapOair) |
One-way from | $109 (Frontier) |
Popular in | July |
Cheapest in | December |
Average price | $295 |
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 2, 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
Tue 10/13
1:10 pm-2:41 pm
Nonstop2h 31m
Chicago O'Hare Intl
Tue 10/20
9:05 am-12:28 pm
Nonstop2h 23m
$257
Quickest round-trip
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 9/29
6:25 pm-7:20 pm
Nonstop1h 55m
Chicago Midway
Mon 10/5
6:50 pm-9:45 pm
Nonstop1h 55m
$257
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 10/13
7:00 am-8:00 am
Nonstop2h 00m
Chicago Midway
Mon 10/19
6:50 pm-9:45 pm
Nonstop1h 55m
$257
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Sat 10/3
10:35 am-9:18 am
1 stop23h 43m
Chicago Greater Rockford
Thu 10/8
9:40 am-1:59 pm
1 stop27h 19m
$260
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Tue 10/6
7:05 am-12:00 pm
1 stop5h 55m
Chicago O'Hare Intl
Sat 10/10
9:05 am-12:28 pm
Nonstop2h 23m
$263
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 10/22
6:55 am-7:55 am
Nonstop2h 00m
Chicago Midway
Mon 10/26
4:30 pm-11:15 pm
1 stop5h 45m
$267
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 11/4
8:50 am-1:59 pm
1 stop6h 09m
Chicago O'Hare Intl
Fri 11/6
7:30 am-10:44 am
Nonstop2h 14m
$274
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Wed 10/14
4:20 pm-8:50 am
2 stops17h 30m
Chicago Greater Rockford
Mon 10/19
10:39 am-9:17 am
1 stop21h 38m
$281
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Wed 11/11
4:20 pm-8:40 am
2 stops17h 20m
Chicago Greater Rockford
Fri 11/13
7:58 pm-8:59 am
1 stop12h 01m
$282
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Thu 11/5
9:30 pm-8:38 am
1 stop12h 08m
Chicago Greater Rockford
Mon 11/9
10:38 am-3:23 pm
2 stops27h 45m
$286
Showing 1-10 of 60 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
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-ORD
RDU-MDW
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 2, 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 21% 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 2, 2026.
The most flights from DU8 to CHI are scheduled on a Tuesday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 $238 and $369 in September.The cheapest round-trip price found within the last 5 days was $232 on Frontier (Sep 21-Sep 28).
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 August 29, 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 2, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
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
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 2, 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 2, 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$63 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$325 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$335 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$184 | Average$320 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$352 | FlexibilityNo cancel fee | On-time63% |