$127+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Aug 12 — Aug 191
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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Best
Last-minute
One-way
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 July 13, 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 July 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 10/94:05 pm
RDU
- ORD
2 stops21h 27m
Frontier
Mon 10/129:33 pm
ORD
- RDU
1 stop16h 14m
Frontier
Deal found 7/13![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 8/126:14 pm
RDU
- ORD
2 stops31h 19m
Frontier
Wed 8/195:59 pm
ORD
- RDU
1 stop13h 19m
Frontier
Deal found 7/13![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 7/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:31 pm
RDU
- ORD
1 stop9h 39m
Frontier
Tue 8/119:57 pm
ORD
- RDU
1 stop12h 34m
Frontier
Deal found 7/12![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/286:14 pm
RDU
- MDW
1 stop28h 49m
Frontier
Thu 8/66:05 am
MDW
- RDU
1 stop25h 06m
Frontier
Deal found 7/9![Frontier logo]()
$262
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/32:31 pm
RDU
- ORD
1 stop9h 39m
Frontier
Wed 8/51:50 pm
ORD
- RDU
1 stop7h 45m
Frontier
Deal found 7/9![Frontier logo]()
$263
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/36:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Wed 8/511:06 am
MDW
- RDU
1 stop10h 29m
Frontier
Deal found 7/9![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:06 pm
RDU
- ORD
1 stop14h 05m
Frontier
Mon 8/178:58 pm
ORD
- RDU
2 stops26h 01m
Frontier
Deal found 7/13![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 8/66:14 pm
RDU
- ORD
1 stop14h 48m
Frontier
Mon 8/108:58 pm
ORD
- RDU
2 stops24h 46m
Frontier
Deal found 7/13![Frontier logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/2911:56 am
RDU
- RFD
2 stops23h 41m
Multiple Airlines
Fri 7/317:50 pm
RFD
- RDU
1 stop12h 10m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
RDU
- MDW
1 stop4h 10m
Southwest
Mon 10/127:05 am
MDW
- RDU
1 stop4h 50m
Southwest
Deal found 7/8![Southwest logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 8/511:56 am
RDU
- ORD
1 stop8h 57m
Frontier
Mon 8/108:58 pm
ORD
- RDU
2 stops24h 46m
Frontier
Deal found 7/13![Frontier logo]()
$266
This Trip.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Tue 8/46:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Tue 8/1111:06 am
MDW
- RDU
1 stop10h 38m
Frontier
Deal found 7/8![Frontier logo]()
$266
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 July 13, 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 July 13, 2026.
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 12/310:30 am
RDU
- ORD
Nonstop2h 15m
United Airlines
Sun 12/62:15 pm
ORD
- RDU
Nonstop1h 54m
United Airlines
Deal found 7/9![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 7/12. 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.
Tue 8/111:25 pm
RDU
- MDW
Nonstop1h 50m
Southwest
Sat 8/157:40 am
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 7/12![Southwest logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/610:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Sun 8/911:37 am
RFD
- RDU
2 stops21h 42m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 12/36:35 am
RDU
- ORD
1 stop4h 32m
Delta
Sun 12/67:05 am
ORD
- RDU
1 stop3h 41m
Delta
Deal found 7/9![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/276:55 am
RDU
- ORD
1 stop6h 04m
United Airlines
Sun 8/307:15 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/9![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/164:40 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Thu 8/203:15 pm
MDW
- RDU
1 stop5h 35m
Southwest
Deal found 7/9![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/265:34 am
RDU
- MDW
1 stop4h 33m
Delta
Sun 9/276:05 am
MDW
- RDU
1 stop4h 21m
Delta
Deal found 7/10![Delta logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/252:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Fri 7/317:50 pm
RFD
- RDU
1 stop12h 10m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/1210:05 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sat 9/126:15 pm
ORD
- RDU
1 stop4h 44m
United Airlines
Deal found 7/8![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:50 pm
RDU
- ORD
1 stop5h 20m
Delta
Mon 11/167:10 am
ORD
- RDU
1 stop4h 39m
Delta
Deal found 7/13![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 7/12. 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.
Thu 8/274:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Sun 8/307:35 am
MDW
- RDU
1 stop4h 35m
Southwest
Deal found 7/12![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/1010:36 am
RDU
- ORD
1 stop4h 51m
United Airlines
Tue 9/159:10 am
ORD
- RDU
Nonstop2h 23m
United Airlines
Deal found 7/8![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:26 pm
RDU
- ORD
1 stop5h 04m
Delta
Sun 9/275:30 am
ORD
- RDU
1 stop4h 56m
Delta
Deal found 7/11![Delta logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 7/249:27 pm
RDU
- RFD
2 stops38h 10m
Multiple Airlines
Fri 7/317:50 pm
RFD
- RDU
1 stop12h 10m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 7/12. 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.
Tue 8/186:00 am
RDU
- MDW
2 stops6h 50m
Southwest
Tue 8/2512:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 7/12![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/288:06 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 8/302:30 pm
ORD
- RDU
Nonstop2h 11m
United Airlines
Deal found 7/8![United Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/27:15 am
RDU
- MDW
Nonstop1h 55m
Southwest
Wed 8/58:35 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/9![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/252:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Mon 7/277:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:10 am
RDU
- MDW
1 stop7h 05m
Delta
Mon 8/176:42 pm
MDW
- RDU
1 stop3h 43m
Delta
Deal found 7/11![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/18:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Tue 8/2512:50 pm
ORD
- RDU
Nonstop2h 11m
United Airlines
Deal found 7/8![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/146:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Sun 8/168:05 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/10![Southwest logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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
RDU
- RFD
2 stops13h 37m
Multiple Airlines
Mon 10/1210:39 am
RFD
- RDU
1 stop25h 35m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/36:00 am
RDU
- ORD
1 stop4h 36m
United Airlines
Wed 8/56:25 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 7/9![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 7/12. 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.
Fri 9/118:25 am
RDU
- MDW
Nonstop1h 50m
Southwest
Sun 9/137:50 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 7/12![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/210:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Mon 8/37:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 7/13. 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 10/236:05 am
RDU
- ORD
Nonstop2h 22m
United Airlines
Sun 10/257:30 am
ORD
- RDU
Nonstop2h 14m
United Airlines
Deal found 7/13![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/46:00 am
RDU
- MDW
2 stops6h 50m
Southwest
Thu 8/610:05 am
MDW
- RDU
2 stops7h 15m
Southwest
Deal found 7/10![Southwest logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:09 pm
RDU
- RFD
2 stops19h 25m
Multiple Airlines
Mon 8/176:26 pm
RFD
- RDU
1 stop14h 26m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 7/13. 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 9/2510:13 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 9/2710:33 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/13![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/12:00 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Tue 8/48:35 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/8![Southwest logo]()
$345
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated July 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/277:32 pm
RDU
- MDW
2 stops16h 35m
Frontier
Thu 8/66:05 am
MDW
- RDU
1 stop25h 06m
Frontier
Deal found 7/9![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/286:14 pm
RDU
- MDW
1 stop28h 49m
Frontier
Thu 8/66:05 am
MDW
- RDU
1 stop25h 06m
Frontier
Deal found 7/9![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/2911:56 am
RDU
- RFD
2 stops23h 41m
Multiple Airlines
Fri 7/317:50 pm
RFD
- RDU
1 stop12h 10m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$265
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/301:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Mon 8/312:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 7/9![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/316:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Tue 8/412:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 7/8![Frontier logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/26:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Wed 8/54:45 pm
MDW
- RDU
2 stops28h 59m
Frontier
Deal found 7/9![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/36:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Wed 8/511:06 am
MDW
- RDU
1 stop10h 29m
Frontier
Deal found 7/9![Frontier logo]()
$263
This Trip.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Tue 8/46:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Tue 8/1111:06 am
MDW
- RDU
1 stop10h 38m
Frontier
Deal found 7/8![Frontier logo]()
$266
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/68:05 am
RDU
- MDW
2 stops7h 25m
Southwest
Tue 8/1112:45 pm
MDW
- RDU
2 stops7h 15m
Southwest
Deal found 7/8![Southwest logo]()
$265
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/712:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Thu 8/1311:06 am
MDW
- RDU
1 stop10h 38m
Frontier
Deal found 7/9![Frontier logo]()
$271
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:25 pm
RDU
- MDW
Nonstop1h 50m
Southwest
Sat 8/153:10 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 7/12![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/166:50 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Thu 8/2012:50 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 7/9![Southwest logo]()
$269
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 July 13, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/56:14 pm
RDU
- ORD
2 stops38h 48m
Frontier
Deal found 7/9![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/316:15 am
RDU
- MDW
1 stop29h 52m
Frontier
Deal found 7/8![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/88:06 pm
RDU
- ORD
2 stops24h 47m
Frontier
Deal found 7/8![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/98:06 pm
RDU
- MDW
2 stops26h 57m
Frontier
Deal found 7/9![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 10/92:09 pm
RDU
- ORD
1 stop8h 25m
Frontier
Deal found 7/9![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/16:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Deal found 7/10![Frontier logo]()
$129
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fri 8/78:17 pm
RDU
- ORD
Nonstop2h 43m
American Airlines
Deal found 7/9![American Airlines logo]()
$130
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/211:15 pm
RDU
- MDW
Nonstop1h 50m
Southwest
Deal found 7/8![Southwest logo]()
$130
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/301:21 pm
RDU
- ORD
1 stop8h 06m
Frontier
Deal found 7/8![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:20 pm
RDU
- RFD
2 stops17h 58m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$132
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/301:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Deal found 7/8![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/276:05 am
RDU
- ORD
2 stops15h 10m
Frontier
Deal found 7/9![Frontier logo]()
$133
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 July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $262 (Frontier) |
One-way from | $127 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $333 |
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 July 13, 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 - ORD
RDUORD
Raleigh-Durham
Thu 12/3
10:30 am-11:45 am
Nonstop2h 15m
Chicago O'Hare Intl
Sun 12/6
2:15 pm-5:09 pm
Nonstop1h 54m
$269
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Tue 8/11
1:25 pm-2:15 pm
Nonstop1h 50m
Chicago Midway
Sat 8/15
7:40 am-10:35 am
Nonstop1h 55m
$272
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Thu 8/27
6:55 am-11:59 am
1 stop6h 04m
Chicago O'Hare Intl
Sun 8/30
7:15 am-10:31 am
Nonstop2h 16m
$275
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sun 8/16
4:40 pm-5:35 pm
Nonstop1h 55m
Chicago Midway
Thu 8/20
3:15 pm-9:50 pm
1 stop5h 35m
$279
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 8/6
10:34 pm-7:49 am
1 stop10h 15m
Chicago Greater Rockford
Sun 8/9
11:37 am-10:19 am
2 stops21h 42m
$282
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Thu 12/3
6:35 am-10:07 am
1 stop4h 32m
Chicago O'Hare Intl
Sun 12/6
7:05 am-11:46 am
1 stop3h 41m
$289
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 9/26
5:34 am-9:07 am
1 stop4h 33m
Chicago Midway
Sun 9/27
6:05 am-11:26 am
1 stop4h 21m
$289
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 9/12
10:05 am-11:29 am
Nonstop2h 24m
Chicago O'Hare Intl
Sat 9/12
6:15 pm-11:59 pm
1 stop4h 44m
$291
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Thu 9/10
10:36 am-2:27 pm
1 stop4h 51m
Chicago O'Hare Intl
Tue 9/15
9:10 am-12:33 pm
Nonstop2h 23m
$291
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Fri 11/13
4:50 pm-9:10 pm
1 stop5h 20m
Chicago O'Hare Intl
Mon 11/16
7:10 am-12:49 pm
1 stop4h 39m
$292
Showing 1-10 of 59 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 July 13, 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 24% 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 July 13, 2026.
The most flights from DU8 to CHI are scheduled on a Friday (38 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Durham to Chicago?
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 July 11, 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 July 13, 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
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 July 13, 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 July 13, 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 July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$73 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$306 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$155 | Average$325 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$330 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$174 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$188 | Average$329 | FlexibilityNo cancel fee | On-time63% |