$118+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Sep 5 — Sep 121
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 82 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 6, 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 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/263:06 pm -
1 stop9h 02m
Sat 8/295:59 pm -
1 stop16h 36m
Deal found 8/3![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/244:49 pm -
2 stops26h 02m
Tue 9/296:25 am -
1 stop5h 13m
Deal found 8/5![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/44:02 pm -
1 stop16h 51m
Sun 9/67:05 am -
1 stop15h 54m
Deal found 8/4![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:56 pm -
1 stop5h 27m
Mon 10/129:33 pm -
1 stop16h 14m
Deal found 8/3![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 stops23h 03m
Sat 9/266:25 am -
1 stop5h 13m
Deal found 8/5![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/249:13 am -
1 stop14h 55m
Thu 8/278:05 am -
2 stops25h 14m
Deal found 8/4![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/29:48 pm -
2 stops25h 59m
Wed 9/96:25 am -
1 stop5h 13m
Deal found 8/5![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:46 pm -
1 stop13h 08m
Wed 11/43:34 pm -
1 stop16h 26m
Deal found 8/5![Multiple Airlines logo]()
$240
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/16:55 am -
1 stop6h 04m
Tue 9/812:29 pm -
Nonstop2h 08m
Deal found 8/4![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:59 pm -
1 stop6h 01m
Tue 11/311:39 am -
1 stop4h 26m
Deal found 8/4![Delta logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/161:56 pm -
2 stops16h 42m
Wed 9/236:20 am -
1 stop17h 09m
Deal found 8/2![Frontier logo]()
$242
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/51:00 pm -
1 stop7h 45m
Tue 9/812:45 pm -
2 stops5h 05m
Deal found 8/4![Southwest logo]()
$242
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 6, 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 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:46 pm -
1 stop13h 08m
Wed 11/43:34 pm -
1 stop16h 26m
Deal found 8/5![Multiple Airlines logo]()
$240
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/16:55 am -
1 stop6h 04m
Mon 9/142:07 pm -
Nonstop2h 11m
Deal found 8/5![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Sun 9/66:00 am -
1 stop4h 40m
Tue 9/87:05 am -
1 stop3h 56m
Deal found 8/4![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/38:20 am -
Nonstop2h 00m
Sat 10/32:40 pm -
1 stop6h 05m
Deal found 8/5![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/267:05 am -
1 stop5h 58m
Mon 9/2810:33 am -
Nonstop2h 16m
Deal found 8/5![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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.
Sat 9/512:46 pm -
1 stop5h 05m
Tue 9/85:10 pm -
1 stop5h 02m
Deal found 8/5![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/2811:25 am -
1 stop6h 25m
Sat 10/319:15 am -
Nonstop2h 00m
Deal found 8/5![Southwest logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 10/89:59 pm -
1 stop11h 03m
Sun 10/1110:30 am -
2 stops12h 47m
Deal found 8/2![Multiple Airlines logo]()
$258
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/56:00 am -
1 stop4h 38m
Sat 9/56:15 pm -
1 stop4h 44m
Deal found 8/5![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 pm -
Nonstop1h 55m
Wed 9/237:40 am -
1 stop4h 00m
Deal found 8/2![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:36 am -
1 stop4h 51m
Sat 9/263:35 pm -
Nonstop2h 13m
Deal found 8/2![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 8/1. 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 9/114:50 pm -
2 stops7h 35m
Mon 9/147:55 am -
1 stop4h 05m
Deal found 8/1![Southwest logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 10/89:59 pm -
1 stop11h 03m
Mon 10/1210:39 am -
1 stop22h 21m
Deal found 8/4![Multiple Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/107:59 pm -
1 stop4h 41m
Mon 9/142:07 pm -
Nonstop2h 11m
Deal found 8/3![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/56:20 am -
2 stops8h 00m
Tue 9/812:45 pm -
2 stops5h 05m
Deal found 8/5![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/1. 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 9/156:55 pm -
1 stop4h 00m
Tue 9/2212:45 pm -
2 stops5h 05m
Deal found 8/1![Southwest logo]()
$256
This United Airlines deal was found by Cheapflights users on 8/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:05 am -
1 stop5h 58m
Fri 10/2310:33 am -
Nonstop2h 16m
Deal found 8/2![United Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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
Mon 9/215:20 pm -
1 stop15h 39m
Deal found 8/4![Multiple Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 8/1. 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.
Thu 9/172:40 pm -
1 stop4h 35m
Wed 9/2312:40 pm -
2 stops5h 15m
Deal found 8/1![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/1. 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 9/46:55 pm -
1 stop4h 05m
Sun 9/68:55 am -
Nonstop2h 00m
Deal found 8/1![Southwest logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 stops12h 41m
Deal found 8/4![Multiple Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:00 am -
Nonstop2h 26m
Thu 1/78:55 am -
1 stop4h 00m
Deal found 8/4![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:45 am -
1 stop9h 15m
Sat 9/267:55 am -
2 stops7h 50m
Deal found 8/2![Southwest logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Fri 10/96:35 am -
2 stops13h 37m
Mon 10/126:13 pm -
1 stop14h 46m
Deal found 8/1![Multiple Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/296:55 am -
1 stop6h 04m
Sun 9/62:30 pm -
Nonstop2h 11m
Deal found 8/3![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/266:40 am -
2 stops7h 25m
Mon 9/285:30 am -
1 stop8h 55m
Deal found 8/5![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:55 pm -
2 stops7h 10m
Mon 11/168:20 am -
1 stop8h 25m
Deal found 8/2![Southwest logo]()
$260
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:25 am -
Nonstop2h 24m
Fri 9/182:07 pm -
Nonstop2h 11m
Deal found 8/3![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Fri 10/210:40 am -
1 stop4h 46m
Sun 10/43:35 pm -
Nonstop2h 13m
Deal found 8/1![United Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/125:13 pm -
2 stops20h 21m
Fri 8/146:26 pm -
1 stop13h 50m
Deal found 8/3![Multiple Airlines logo]()
$480
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated August 6, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sun 8/168:06 pm -
2 stops36h 47m
Wed 8/191:59 pm -
1 stop17h 33m
Deal found 8/2![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 8/2010:11 pm -
1 stop10h 42m
Tue 8/251:59 pm -
1 stop9h 00m
Deal found 8/2![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/249:13 am -
1 stop14h 55m
Thu 8/278:05 am -
2 stops25h 14m
Deal found 8/4![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/263:06 pm -
1 stop9h 02m
Sat 8/295:59 pm -
1 stop16h 36m
Deal found 8/3![Multiple Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/16:55 am -
1 stop6h 04m
Tue 9/812:29 pm -
Nonstop2h 08m
Deal found 8/4![United Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/29:48 pm -
2 stops25h 59m
Wed 9/96:25 am -
1 stop5h 13m
Deal found 8/5![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/44:02 pm -
1 stop16h 51m
Sun 9/67:05 am -
1 stop15h 54m
Deal found 8/4![Frontier logo]()
$238
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/51:00 pm -
1 stop7h 45m
Tue 9/812:45 pm -
2 stops5h 05m
Deal found 8/4![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/129:46 pm -
2 stops21h 00m
Mon 9/146:46 pm -
1 stop4h 43m
Deal found 8/5![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/161:56 pm -
2 stops16h 42m
Wed 9/236:20 am -
1 stop17h 09m
Deal found 8/2![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 stops23h 03m
Sat 9/266:25 am -
1 stop5h 13m
Deal found 8/5![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/244:49 pm -
2 stops26h 02m
Tue 9/296:25 am -
1 stop5h 13m
Deal found 8/5![Frontier logo]()
$237
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 6, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/710:05 am -
Nonstop2h 24m
Deal found 8/4![United Airlines logo]()
$118
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/28:20 am -
Nonstop1h 50m
Deal found 8/4![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/66:50 am -
2 stops5h 50m
Deal found 8/5![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/196:05 am -
1 stop15h 03m
Deal found 8/2![Frontier logo]()
$120
This Trip.com deal was found by Cheapflights users on 8/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:15 am -
1 stop16h 48m
Deal found 8/2![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:33 pm -
2 stops20h 47m
Deal found 8/5![Multiple Airlines logo]()
$121
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/36:05 am -
1 stop5h 50m
Deal found 8/3![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/41:56 pm -
1 stop4h 50m
Deal found 8/3![Frontier logo]()
$122
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/316:55 am -
1 stop6h 04m
Deal found 8/4![United Airlines logo]()
$123
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/131:56 pm -
1 stop4h 50m
Deal found 8/4![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Mon 8/176:15 am -
1 stop26h 38m
Deal found 8/2![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/49:35 pm -
1 stop13h 19m
Deal found 8/3![Multiple Airlines logo]()
$125
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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Kiwi.com) |
One-way from | $118 (United Airlines) |
Popular in | July |
Cheapest in | December |
Average price | $297 |
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 6, 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
Sun 11/1
9:46 pm-9:54 am
1 stop13h 08m
Chicago Greater Rockford
Wed 11/4
3:34 pm-9:00 am
1 stop16h 26m
$240
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Tue 9/1
6:55 am-11:59 am
1 stop6h 04m
Chicago O'Hare Intl
Mon 9/14
2:07 pm-5:18 pm
Nonstop2h 11m
$241
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sun 9/6
6:00 am-9:40 am
1 stop4h 40m
Chicago O'Hare Intl
Tue 9/8
7:05 am-12:01 pm
1 stop3h 56m
$241
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sat 9/26
7:05 am-12:03 pm
1 stop5h 58m
Chicago O'Hare Intl
Mon 9/28
10:33 am-1:49 pm
Nonstop2h 16m
$241
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sat 9/5
12:46 pm-4:51 pm
1 stop5h 05m
Chicago O'Hare Intl
Tue 9/8
5:10 pm-11:12 pm
1 stop5h 02m
$241
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Sat 9/5
6:00 am-9:38 am
1 stop4h 38m
Chicago O'Hare Intl
Sat 9/5
6:15 pm-11:59 pm
1 stop4h 44m
$241
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Sat 10/3
8:20 am-9:20 am
Nonstop2h 00m
Chicago Midway
Sat 10/3
2:40 pm-9:45 pm
1 stop6h 05m
$245
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Wed 10/28
11:25 am-4:50 pm
1 stop6h 25m
Chicago Midway
Sat 10/31
9:15 am-12:15 pm
Nonstop2h 00m
$245
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Wed 9/16
6:25 pm-7:20 pm
Nonstop1h 55m
Chicago Midway
Wed 9/23
7:40 am-12:40 pm
1 stop4h 00m
$245
RaleighChicago
RDU Raleigh-Durham - ORD Chicago O'Hare Intl
RDUORD
Raleigh-Durham
Wed 9/23
10:36 am-2:27 pm
1 stop4h 51m
Chicago O'Hare Intl
Sat 9/26
3:35 pm-6:48 pm
Nonstop2h 13m
$245
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-RFD
RDU-ORD
RDU-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Durham to Chicago
DU8-CHI
RDU-RFD
RDU-ORD
RDU-MDW
What is the cheapest time of day to fly from DU8 to CHI?
Find hourly flight availability from Durham to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 6, 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 6, 2026.
The most flights from DU8 to CHI are scheduled on a Tuesday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 $206 and $338 in August.The cheapest round-trip price found within the last 5 days was $237 on Multiple Airlines (Aug 26-Aug 29).
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 1, 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 6, 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.
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
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 6, 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 6, 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$317 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$330 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$328 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$188 | Average$342 | FlexibilityNo cancel fee | On-time63% |