$113+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Sep 16 — Sep 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 August 17, 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 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Tue 9/221:56 pm -
1 stop22h 55m
Fri 9/253:50 pm -
2 stops16h 50m
Deal found 8/15![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Fri 9/116:35 am -
2 stops30h 24m
Mon 9/146:25 am -
1 stop5h 13m
Deal found 8/15![Frontier logo]()
$234
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:17 pm -
1 stop7h 06m
Sun 9/272:46 pm -
1 stop22h 18m
Deal found 8/13![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:56 pm -
1 stop4h 55m
Sun 9/206:46 pm -
1 stop4h 43m
Deal found 8/15![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/1710:35 am -
1 stop29h 10m
Mon 9/217:28 pm -
1 stop16h 10m
Deal found 8/15![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/225:48 pm -
2 stops25h 03m
Mon 9/286:46 pm -
1 stop4h 43m
Deal found 8/16![Frontier logo]()
$236
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:14 pm -
Nonstop2h 48m
Fri 9/49:30 am -
Nonstop2h 18m
Deal found 8/13![American Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/53:50 pm -
Nonstop2h 00m
Sun 9/68:55 am -
Nonstop2h 00m
Deal found 8/13![Southwest logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/106:35 am -
1 stop12h 48m
Sun 9/1310:26 am -
1 stop13h 03m
Deal found 8/14![Frontier logo]()
$238
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:15 pm -
1 stop7h 32m
Sun 9/611:50 am -
1 stop11h 09m
Deal found 8/13![Frontier logo]()
$238
This KAYAK deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:10 pm -
1 stop4h 45m
Thu 9/35:30 am -
1 stop5h 07m
Deal found 8/13![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:50 pm -
2 stops7h 30m
Wed 9/212:45 pm -
2 stops5h 05m
Deal found 8/12![Southwest 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 August 17, 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 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/299:42 pm -
1 stop11h 12m
Mon 11/25:55 pm -
1 stop15h 04m
Deal found 8/14![Multiple Airlines logo]()
$239
This JetBlue deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:00 am -
1 stop7h 45m
Fri 9/253:00 pm -
1 stop6h 19m
Deal found 8/16![JetBlue logo]()
$255
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/151:25 pm -
Nonstop1h 50m
Tue 9/222:40 pm -
Nonstop1h 55m
Deal found 8/16![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:00 am -
Nonstop2h 24m
Sun 10/1110:33 am -
Nonstop2h 16m
Deal found 8/12![United Airlines logo]()
$277
This KAYAK deal was found by Cheapflights users on 8/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:45 pm -
1 stop6h 26m
Fri 10/235:29 pm -
1 stop5h 12m
Deal found 8/14![Delta logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/109:35 pm -
1 stop12h 17m
Mon 9/145:20 pm -
1 stop15h 39m
Deal found 8/14![Multiple Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:45 am -
Nonstop2h 10m
Sat 1/22:24 pm -
Nonstop2h 06m
Deal found 8/13![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:05 pm -
Nonstop1h 55m
Sun 10/117:45 am -
Nonstop2h 00m
Deal found 8/12![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/14. 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 10/176:40 pm -
1 stop4h 00m
Thu 10/228:00 am -
Nonstop2h 00m
Deal found 8/14![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:05 am -
1 stop5h 55m
Sun 10/119:05 am -
Nonstop2h 23m
Deal found 8/13![United Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 10/89:46 pm -
1 stop11h 16m
Fri 10/98:02 pm -
1 stop11h 57m
Deal found 8/12![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 11/51:45 pm -
Nonstop2h 05m
Sun 11/87:45 am -
Nonstop1h 55m
Deal found 8/13![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/96:05 am -
Nonstop2h 22m
Tue 10/1312:55 pm -
Nonstop2h 08m
Deal found 8/16![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 10/18:45 pm -
1 stop4h 10m
Sun 10/48:55 pm -
Nonstop2h 00m
Deal found 8/13![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Wed 9/91:14 pm -
1 stop22h 51m
Sun 9/139:29 pm -
2 stops34h 40m
Deal found 8/15![Multiple Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:50 am -
1 stop6h 22m
Sun 11/1510:35 am -
Nonstop2h 09m
Deal found 8/16![United Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/98:45 pm -
1 stop4h 10m
Tue 10/136:10 pm -
Nonstop1h 55m
Deal found 8/16![Southwest logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:29 am -
Nonstop2h 25m
Sun 9/69:10 am -
Nonstop2h 23m
Deal found 8/13![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 8/15. 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.
Wed 10/146:50 pm -
Nonstop2h 00m
Sun 10/187:45 am -
Nonstop2h 00m
Deal found 8/15![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/229:30 pm -
1 stop11h 24m
Sun 10/258:53 pm -
2 stops13h 18m
Deal found 8/15![Multiple Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Sat 9/193:05 pm -
1 stop4h 32m
Sun 9/207:24 am -
Nonstop2h 23m
Deal found 8/15![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/297:20 pm -
Nonstop2h 00m
Sun 11/17:45 am -
Nonstop1h 55m
Deal found 8/16![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/188:00 am -
Nonstop2h 24m
Sun 9/2012:50 pm -
Nonstop2h 12m
Deal found 8/16![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sun 9/134:40 pm -
Nonstop1h 55m
Fri 9/186:30 pm -
Nonstop2h 00m
Deal found 8/12![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/179:35 pm -
1 stop12h 17m
Mon 9/215:20 pm -
1 stop15h 39m
Deal found 8/13![Multiple Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 8/14. 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 10/208:00 am -
Nonstop2h 24m
Thu 10/229:05 am -
Nonstop2h 23m
Deal found 8/14![United Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/96:25 am -
Nonstop2h 24m
Wed 9/96:28 pm -
Nonstop2h 21m
Deal found 8/16![United Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/179:46 pm -
1 stop19h 29m
Sun 9/209:29 pm -
2 stops15h 35m
Deal found 8/13![Multiple Airlines logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Mon 9/149:53 am -
2 stops27h 58m
Fri 9/185:05 pm -
1 stop14h 54m
Deal found 8/12![Multiple Airlines logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Fri 8/219:13 am -
1 stop9h 53m
Sun 8/239:35 pm -
2 stops20h 34m
Deal found 8/15![Multiple Airlines logo]()
$658
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated August 17, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:10 pm -
1 stop4h 45m
Thu 9/35:30 am -
1 stop5h 07m
Deal found 8/13![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:50 pm -
2 stops7h 30m
Wed 9/212:45 pm -
2 stops5h 05m
Deal found 8/12![Southwest logo]()
$239
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:14 pm -
Nonstop2h 48m
Fri 9/49:30 am -
Nonstop2h 18m
Deal found 8/13![American Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/53:50 pm -
Nonstop2h 00m
Sun 9/68:55 am -
Nonstop2h 00m
Deal found 8/13![Southwest logo]()
$237
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:15 pm -
1 stop7h 32m
Sun 9/611:50 am -
1 stop11h 09m
Deal found 8/13![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/106:35 am -
1 stop12h 48m
Sun 9/1310:26 am -
1 stop13h 03m
Deal found 8/14![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Fri 9/116:35 am -
2 stops30h 24m
Mon 9/146:25 am -
1 stop5h 13m
Deal found 8/15![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/1710:35 am -
1 stop29h 10m
Mon 9/217:28 pm -
1 stop16h 10m
Deal found 8/15![Frontier logo]()
$236
This Expedia deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Fri 9/181:56 pm -
1 stop4h 55m
Sun 9/206:46 pm -
1 stop4h 43m
Deal found 8/16![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Tue 9/221:56 pm -
1 stop22h 55m
Fri 9/253:50 pm -
2 stops16h 50m
Deal found 8/15![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/225:48 pm -
2 stops25h 03m
Mon 9/286:46 pm -
1 stop4h 43m
Deal found 8/17![Frontier logo]()
$236
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:17 pm -
1 stop7h 06m
Sun 9/272:46 pm -
1 stop22h 18m
Deal found 8/13![Frontier logo]()
$235
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 17, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1010:35 am -
2 stops15h 10m
Deal found 8/13![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 10/29:03 pm -
2 stops21h 48m
Deal found 8/13![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sun 8/309:59 pm -
1 stop26h 09m
Deal found 8/14![Frontier logo]()
$114
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:45 pm -
1 stop4h 10m
Deal found 8/12![Southwest logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 8/298:16 pm -
2 stops36h 37m
Deal found 8/13![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Tue 10/205:26 pm -
2 stops43h 56m
Deal found 8/14![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/231:56 pm -
2 stops16h 42m
Deal found 8/13![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:30 pm -
1 stop11h 01m
Deal found 8/15![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 8/14. 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 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
Deal found 8/14![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/2211:10 am -
2 stops14h 16m
Deal found 8/14![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Mon 11/169:46 pm -
2 stops25h 07m
Deal found 8/13![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1010:35 am -
2 stops14h 09m
Deal found 8/13![Frontier logo]()
$119
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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $234 (Kiwi.com) |
One-way from | $113 (Kiwi.com) |
Popular in | July |
Cheapest in | December |
Average price | $304 |
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 2,558,603 searches. Data last updated August 17, 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
Thu 10/29
9:42 pm-7:54 am
1 stop11h 12m
Chicago Greater Rockford
Mon 11/2
5:55 pm-9:59 am
1 stop15h 04m
$239
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Tue 9/22
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Fri 9/25
3:00 pm-10:19 pm
1 stop6h 19m
$255
RaleighChicago
RDU Raleigh-Durham - RFD Chicago Greater Rockford
RDURFD
Raleigh-Durham
Thu 9/10
9:35 pm-8:52 am
1 stop12h 17m
Chicago Greater Rockford
Mon 9/14
5:20 pm-9:59 am
1 stop15h 39m
$262
Quickest round-trip
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 9/15
1:25 pm-2:15 pm
Nonstop1h 50m
Chicago Midway
Tue 9/22
2:40 pm-5:35 pm
Nonstop1h 55m
$267
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sat 10/10
8:00 am-9:24 am
Nonstop2h 24m
Chicago O'Hare Intl
Sun 10/11
10:33 am-1:49 pm
Nonstop2h 16m
$277
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Thu 12/24
6:45 am-7:55 am
Nonstop2h 10m
Chicago O'Hare Intl
Sat 1/2
2:24 pm-5:30 pm
Nonstop2h 06m
$277
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Sat 10/10
5:05 pm-6:00 pm
Nonstop1h 55m
Chicago Midway
Sun 10/11
7:45 am-10:45 am
Nonstop2h 00m
$277
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Sat 10/17
6:40 pm-9:40 pm
1 stop4h 00m
Chicago Midway
Thu 10/22
8:00 am-11:00 am
Nonstop2h 00m
$277
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 11/5
1:45 pm-2:50 pm
Nonstop2h 05m
Chicago Midway
Sun 11/8
7:45 am-10:40 am
Nonstop1h 55m
$277
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sat 10/3
7:05 am-12:00 pm
1 stop5h 55m
Chicago O'Hare Intl
Sun 10/11
9:05 am-12:28 pm
Nonstop2h 23m
$283
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 August 17, 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 August 17, 2026.
The most flights from DU8 to CHI are scheduled on a Friday (37 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (26 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 $237 and $353 in September.The cheapest round-trip price found within the last 5 days was $234 on Frontier (Sep 22-Sep 25).
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 15, 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 17, 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
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 August 17, 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 17, 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 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$317 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$171 | Average$333 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$346 | FlexibilityNo cancel fee | On-time63% |