$110+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Sep 27 — Oct 41
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 August 28, 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 August 28, 2026.
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/12:49 pm -
1 stop9h 10m
Sat 10/109:00 am -
1 stop6h 31m
Deal found 8/26![Frontier logo]()
$228
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/11:56 pm -
1 stop4h 50m
Tue 10/66:25 am -
1 stop5h 13m
Deal found 8/26![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/102:54 pm -
1 stop8h 45m
Sat 10/176:30 am -
1 stop8h 54m
Deal found 8/26![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:56 pm -
1 stop10h 48m
Mon 9/216:46 pm -
1 stop4h 43m
Deal found 8/23![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:17 pm -
1 stop7h 06m
Mon 10/128:11 pm -
1 stop12h 06m
Deal found 8/23![Frontier logo]()
$230
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/281:56 pm -
1 stop4h 55m
Thu 10/16:25 am -
1 stop5h 13m
Deal found 8/26![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 10/146:30 am -
1 stop10h 10m
Deal found 8/23![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:56 pm -
1 stop4h 55m
Wed 10/146:15 am -
1 stop8h 06m
Deal found 8/23![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:35 am -
1 stop29h 45m
Thu 10/17:28 pm -
1 stop28h 01m
Deal found 8/23![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/2910:07 am -
1 stop13h 52m
Sat 10/37:11 am -
2 stops25h 51m
Deal found 8/25![Multiple Airlines logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Thu 10/11:56 pm -
1 stop4h 50m
Sat 10/36:25 am -
1 stop5h 13m
Deal found 8/25![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/910:05 am -
1 stop30h 31m
Fri 10/168:04 am -
1 stop28h 55m
Deal found 8/25![Frontier logo]()
$234
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 August 28, 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 August 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Thu 10/159:40 am -
2 stops32h 13m
Deal found 8/27![Multiple Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/2311:35 am -
Nonstop2h 31m
Wed 9/3012:55 pm -
Nonstop2h 08m
Deal found 8/26![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/211:15 pm -
Nonstop1h 50m
Sat 9/263:10 pm -
Nonstop2h 00m
Deal found 8/25![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:34 am -
1 stop6h 03m
Thu 9/105:10 pm -
1 stop5h 02m
Deal found 8/27![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2810:13 am -
Nonstop2h 24m
Thu 10/13:35 pm -
Nonstop2h 13m
Deal found 8/27![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/231:25 pm -
Nonstop1h 50m
Wed 9/302:40 pm -
Nonstop1h 55m
Deal found 8/27![Southwest logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 8/26![Multiple Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/2111:29 am -
Nonstop2h 31m
Sat 9/266:25 pm -
Nonstop2h 21m
Deal found 8/25![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/245:05 pm -
Nonstop1h 55m
Tue 10/277:55 am -
Nonstop2h 00m
Deal found 8/25![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:05 am -
Nonstop2h 25m
Tue 10/69:05 am -
Nonstop2h 23m
Deal found 8/23![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/286:05 pm -
1 stop5h 40m
Sat 10/34:20 pm -
Nonstop1h 55m
Deal found 8/24![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/129:30 pm -
1 stop12h 08m
Sun 11/1511:30 am -
1 stop20h 33m
Deal found 8/24![Multiple Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:50 am -
1 stop6h 09m
Mon 11/21:10 pm -
Nonstop2h 07m
Deal found 8/23![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/17:50 pm -
1 stop4h 15m
Mon 10/56:50 pm -
Nonstop1h 55m
Deal found 8/27![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:05 pm -
1 stop6h 15m
Mon 9/216:30 pm -
Nonstop2h 00m
Deal found 8/23![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/210:13 am -
Nonstop2h 24m
Mon 10/56:25 pm -
Nonstop2h 21m
Deal found 8/25![United Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/229:30 pm -
1 stop11h 24m
Sun 10/258:53 pm -
2 stops13h 18m
Deal found 8/24![Multiple Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/102:20 pm -
1 stop7h 15m
Sat 10/174:20 pm -
Nonstop1h 55m
Deal found 8/26![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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
Sun 9/279:29 pm -
2 stops26h 00m
Deal found 8/26![Multiple Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:25 am -
Nonstop2h 24m
Thu 10/110:33 am -
Nonstop2h 16m
Deal found 8/26![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/1710:15 am -
2 stops8h 05m
Sat 10/2411:25 am -
2 stops9h 25m
Deal found 8/27![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Sun 11/810:35 am -
Nonstop2h 09m
Deal found 8/27![United Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/109:35 pm -
1 stop12h 17m
Sun 9/139:29 pm -
2 stops12h 41m
Deal found 8/27![Multiple Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/123:50 pm -
Nonstop2h 00m
Tue 9/152:40 pm -
Nonstop1h 55m
Deal found 8/24![Southwest logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/159:30 pm -
1 stop11h 29m
Sun 10/189:33 pm -
2 stops15h 27m
Deal found 8/24![Multiple Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:30 am -
Nonstop1h 50m
Mon 9/148:50 am -
Nonstop2h 00m
Deal found 8/23![Southwest logo]()
$308
This KAYAK deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:05 am -
Nonstop2h 22m
Thu 10/19:05 am -
Nonstop2h 23m
Deal found 8/24![United Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/210:40 am -
1 stop4h 46m
Sun 10/43:35 pm -
Nonstop2h 13m
Deal found 8/25![United Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/19:35 pm -
1 stop11h 24m
Sun 10/49:36 pm -
2 stops25h 53m
Deal found 8/27![Multiple Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/210:05 am -
Nonstop2h 24m
Sun 9/62:30 pm -
Nonstop2h 11m
Deal found 8/25![United Airlines logo]()
$396
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated August 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/91:56 pm -
1 stop4h 55m
Fri 9/116:25 am -
1 stop5h 13m
Deal found 8/27![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/91:56 pm -
1 stop4h 55m
Wed 9/166:25 am -
1 stop5h 13m
Deal found 8/27![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/91:56 pm -
1 stop4h 55m
Sat 9/126:25 am -
1 stop5h 13m
Deal found 8/26![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:56 pm -
1 stop10h 48m
Mon 9/216:46 pm -
1 stop4h 43m
Deal found 8/23![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:35 am -
1 stop29h 10m
Mon 9/217:28 pm -
1 stop16h 10m
Deal found 8/23![Frontier logo]()
$235
This Orbitz deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Thu 9/249:35 pm -
1 stop26h 24m
Sat 9/266:30 am -
1 stop9h 52m
Deal found 8/26![Frontier logo]()
$228
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Thu 9/241:56 pm -
1 stop4h 50m
Sun 9/276:46 pm -
1 stop4h 43m
Deal found 8/27![Frontier logo]()
$228
This Travelocity deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:56 pm -
1 stop5h 27m
Fri 10/22:46 pm -
1 stop22h 17m
Deal found 8/26![Frontier logo]()
$234
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/251:56 pm -
1 stop4h 55m
Fri 10/26:46 pm -
1 stop4h 43m
Deal found 8/26![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/281:56 pm -
1 stop4h 55m
Thu 10/16:25 am -
1 stop5h 13m
Deal found 8/26![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:35 am -
1 stop29h 45m
Thu 10/17:28 pm -
1 stop28h 01m
Deal found 8/23![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/2910:07 am -
1 stop13h 52m
Sat 10/37:11 am -
2 stops25h 51m
Deal found 8/25![Multiple Airlines logo]()
$233
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 August 28, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Tue 9/151:56 pm -
1 stop5h 27m
Deal found 8/27![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Tue 9/151:56 pm -
1 stop4h 50m
Deal found 8/26![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/91:56 pm -
1 stop5h 27m
Deal found 8/26![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/261:56 pm -
1 stop4h 55m
Deal found 8/26![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2111:55 am -
1 stop8h 40m
Deal found 8/24![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:35 pm -
1 stop12h 17m
Deal found 8/23![Multiple Airlines logo]()
$112
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/161:56 pm -
1 stop4h 55m
Deal found 8/26![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/1612:21 pm -
1 stop8h 10m
Deal found 8/26![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/239:35 pm -
2 stops18h 28m
Deal found 8/24![Multiple Airlines logo]()
$113
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/245:19 pm -
1 stop8h 05m
Deal found 8/27![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/11:56 pm -
1 stop5h 27m
Deal found 8/25![Frontier logo]()
$115
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/221:56 pm -
1 stop4h 50m
Deal found 8/25![Frontier logo]()
$115
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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $228 (Frontier) |
One-way from | $110 (Super.com) |
Popular in | July |
Cheapest in | December |
Average price | $314 |
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 August 28, 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 - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Wed 10/7
1:14 pm-9:51 am
1 stop21h 37m
Chicago Greater Rockford
Thu 10/15
9:40 am-6:53 pm
2 stops32h 13m
$238
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 9/23
11:35 am-1:06 pm
Nonstop2h 31m
Chicago O'Hare Intl
Wed 9/30
12:55 pm-4:03 pm
Nonstop2h 08m
$267
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 9/21
1:15 pm-2:05 pm
Nonstop1h 50m
Chicago Midway
Sat 9/26
3:10 pm-6:10 pm
Nonstop2h 00m
$267
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Mon 9/28
10:13 am-11:37 am
Nonstop2h 24m
Chicago O'Hare Intl
Thu 10/1
3:35 pm-6:48 pm
Nonstop2h 13m
$267
Quickest round-trip
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Wed 9/23
1:25 pm-2:15 pm
Nonstop1h 50m
Chicago Midway
Wed 9/30
2:40 pm-5:35 pm
Nonstop1h 55m
$267
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Mon 9/21
11:29 am-1:00 pm
Nonstop2h 31m
Chicago O'Hare Intl
Sat 9/26
6:25 pm-9:46 pm
Nonstop2h 21m
$267
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Sat 10/24
5:05 pm-6:00 pm
Nonstop1h 55m
Chicago Midway
Tue 10/27
7:55 am-10:55 am
Nonstop2h 00m
$267
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sat 10/3
8:05 am-9:30 am
Nonstop2h 25m
Chicago O'Hare Intl
Tue 10/6
9:05 am-12:28 pm
Nonstop2h 23m
$267
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Thu 10/29
8:50 am-1:59 pm
1 stop6h 09m
Chicago O'Hare Intl
Mon 11/2
1:10 pm-4:17 pm
Nonstop2h 07m
$273
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 9/28
6:05 pm-10:45 pm
1 stop5h 40m
Chicago Midway
Sat 10/3
4:20 pm-7:15 pm
Nonstop1h 55m
$277
Showing 1-10 of 56 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 August 28, 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 August 28, 2026.
The most flights from DU8 to CHI are scheduled on a Wednesday (36 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 typical for this route at the moment.
Durham to Chicago flights typically cost between $221 and $359 in October.The cheapest round-trip price found within the last 5 days was $228 on Frontier (Oct 1-Oct 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 August 22, 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 August 28, 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.
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
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 August 28, 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 August 28, 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 August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$197 | 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$173 | Average$334 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$181 | Average$319 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$349 | FlexibilityNo cancel fee | On-time63% |