$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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jul 12 — Jul 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 81 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 June 12, 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 June 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/76:15 am
RDU
- ORD
1 stop26h 38m
Frontier
Sun 7/128:05 am
ORD
- RDU
1 stop8h 04m
Frontier
Deal found 6/10![Frontier logo]()
$247
This Southwest deal was found by Cheapflights users on 6/8. 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 11/78:10 am
RDU
- MDW
Nonstop2h 05m
Southwest
Tue 11/101:15 pm
MDW
- RDU
2 stops7h 40m
Southwest
Deal found 6/8![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Mon 7/612:04 pm
RDU
- ORD
1 stop20h 49m
Frontier
Fri 7/101:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/10![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 6/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Tue 7/1412:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/8![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/146:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Tue 9/19:48 pm
ORD
- RDU
2 stops25h 41m
Frontier
Deal found 6/10![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 6/10. 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.
Sun 7/126:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Tue 7/1412:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/10![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 6/3012:54 pm
RDU
- ORD
1 stop7h 56m
Frontier
Wed 7/151:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/9![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 6/10. 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.
Thu 8/2012:54 pm
RDU
- MDW
1 stop10h 17m
Frontier
Sun 8/236:00 am
MDW
- RDU
1 stop4h 59m
Frontier
Deal found 6/10![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/106:15 am
RDU
- ORD
2 stops43h 34m
Multiple Airlines
Wed 7/155:13 pm
ORD
- RDU
1 stop14h 47m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Sun 7/266:14 pm
RDU
- ORD
1 stop14h 39m
Frontier
Sun 8/27:05 am
ORD
- RDU
1 stop24h 06m
Frontier
Deal found 6/11![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 6/9. 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.
Tue 7/76:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Thu 7/912:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/9![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 6/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/411:47 am
RDU
- MDW
1 stop11h 24m
Frontier
Sat 7/1112:11 pm
MDW
- RDU
1 stop10h 52m
Frontier
Deal found 6/8![Frontier logo]()
$253
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 June 12, 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 June 12, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1012:53 pm
RDU
- ORD
1 stop4h 58m
Delta
Wed 8/123:25 pm
ORD
- RDU
1 stop4h 42m
Delta
Deal found 6/8![Delta logo]()
$250
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 8/56:25 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Wed 8/126:00 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/8![Southwest logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/99:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Thu 7/1611:27 am
RFD
- RDU
2 stops21h 52m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/301:15 pm
RDU
- ORD
Nonstop2h 30m
United Airlines
Sat 7/46:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/11![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 8/129:53 am
RDU
- ORD
1 stop4h 15m
Delta
Mon 8/176:40 am
ORD
- RDU
1 stop6h 40m
Delta
Deal found 6/11![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:05 pm
RDU
- MDW
1 stop6h 10m
Southwest
Mon 8/108:50 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/11![Southwest logo]()
$271
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:12 pm
RDU
- ORD
Nonstop2h 30m
United Airlines
Tue 7/1410:48 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/10![United Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/309:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Mon 8/37:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 8/274:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Sat 8/299:20 am
MDW
- RDU
2 stops10h 35m
Southwest
Deal found 6/9![Southwest logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/38:29 pm
RDU
- RFD
1 stop13h 46m
Multiple Airlines
Fri 7/107:50 pm
RFD
- RDU
1 stop12h 10m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:00 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Fri 7/316:55 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/11![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:12 pm
RDU
- ORD
Nonstop2h 30m
United Airlines
Fri 7/244:00 pm
ORD
- RDU
1 stop6h 39m
United Airlines
Deal found 6/10![United Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Sun 7/129:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Thu 7/1611:27 am
RFD
- RDU
2 stops21h 52m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:20 pm
RDU
- ORD
1 stop4h 04m
Delta
Fri 11/279:30 am
ORD
- RDU
1 stop5h 07m
Delta
Deal found 6/8![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/74:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Mon 8/108:50 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/11![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:05 am
RDU
- ORD
1 stop5h 58m
United Airlines
Tue 10/1312:55 pm
ORD
- RDU
Nonstop2h 08m
United Airlines
Deal found 6/7![United Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Sat 7/182:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Mon 7/207:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 9/48:06 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Mon 9/77:10 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 6/7![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/227:00 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Tue 7/2811:25 am
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 6/7![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 6/3010:22 pm
RDU
- RFD
1 stop11h 51m
Multiple Airlines
Fri 7/107:50 pm
RFD
- RDU
1 stop12h 10m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1210:00 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Sun 8/306:28 pm
ORD
- RDU
Nonstop2h 21m
United Airlines
Deal found 6/10![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/99:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Mon 7/137:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$330
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:25 pm
RDU
- MDW
1 stop3h 55m
Southwest
Sun 8/168:05 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/11![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/2310:32 am
RDU
- ORD
1 stop4h 57m
United Airlines
Sun 7/266:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/8![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 6/10. 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 7/288:25 am
RDU
- MDW
2 stops6h 40m
Southwest
Thu 7/302:45 pm
MDW
- RDU
2 stops6h 40m
Southwest
Deal found 6/10![Southwest logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 6/258:30 pm
RDU
- RFD
1 stop12h 15m
Multiple Airlines
Mon 6/297:48 pm
RFD
- RDU
1 stop12h 31m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Mon 8/106:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/11![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 6/10. 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 7/711:15 am
RDU
- MDW
2 stops6h 50m
Southwest
Fri 7/107:55 am
MDW
- RDU
2 stops8h 00m
Southwest
Deal found 6/10![Southwest logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 6/268:29 pm
RDU
- RFD
1 stop13h 48m
Multiple Airlines
Mon 6/297:48 pm
RFD
- RDU
1 stop21h 02m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/41:15 pm
RDU
- ORD
Nonstop2h 30m
United Airlines
Wed 7/86:30 am
ORD
- RDU
1 stop6h 38m
United Airlines
Deal found 6/10![United Airlines logo]()
$365
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated June 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 6/3012:54 pm
RDU
- ORD
1 stop7h 56m
Frontier
Wed 7/151:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/9![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 6/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/411:47 am
RDU
- MDW
1 stop11h 24m
Frontier
Sat 7/1112:11 pm
MDW
- RDU
1 stop10h 52m
Frontier
Deal found 6/8![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Mon 7/612:04 pm
RDU
- ORD
1 stop20h 49m
Frontier
Fri 7/101:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/10![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/76:15 am
RDU
- ORD
1 stop26h 38m
Frontier
Sun 7/128:05 am
ORD
- RDU
1 stop8h 04m
Frontier
Deal found 6/10![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 6/9. 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.
Tue 7/76:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Thu 7/912:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/9![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 6/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Tue 7/1412:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/8![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/1012:04 pm
RDU
- MDW
1 stop24h 03m
Frontier
Wed 7/156:05 am
MDW
- RDU
1 stop16h 59m
Frontier
Deal found 6/11![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Fri 7/106:15 am
RDU
- ORD
2 stops43h 34m
Multiple Airlines
Wed 7/155:13 pm
ORD
- RDU
1 stop14h 47m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$251
This Frontier deal was found by Cheapflights users on 6/10. 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.
Sun 7/126:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Tue 7/1412:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/10![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/146:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Tue 9/19:48 pm
ORD
- RDU
2 stops25h 41m
Frontier
Deal found 6/10![Frontier logo]()
$249
This Southwest deal was found by Cheapflights users on 6/12. 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 7/226:00 am
RDU
- MDW
1 stop6h 00m
Southwest
Wed 7/297:40 am
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/12![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Sun 7/266:14 pm
RDU
- ORD
1 stop14h 39m
Frontier
Sun 8/27:05 am
ORD
- RDU
1 stop24h 06m
Frontier
Deal found 6/11![Frontier logo]()
$252
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 June 12, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Tue 8/48:56 am
RDU
- ORD
1 stop28h 19m
Frontier
Deal found 6/8![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/711:51 am
RDU
- MDW
1 stop11h 20m
Frontier
Deal found 6/7![Frontier logo]()
$127
This Trip.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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.
Mon 7/136:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Deal found 6/7![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/2912:10 pm
RDU
- ORD
1 stop20h 53m
Frontier
Deal found 6/7![Frontier logo]()
$129
This Priceline deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:15 am
RDU
- MDW
1 stop5h 49m
Frontier
Deal found 6/7![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/2012:04 pm
RDU
- ORD
1 stop20h 49m
Frontier
Deal found 6/7![Frontier logo]()
$130
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/2012:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Deal found 6/7![Frontier logo]()
$130
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/810:59 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Deal found 6/11![United Airlines logo]()
$131
This Southwest deal was found by Cheapflights users on 6/8. 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 9/57:30 am
RDU
- MDW
Nonstop1h 50m
Southwest
Deal found 6/8![Southwest logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/2110:22 pm
RDU
- RFD
2 stops35h 07m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$131
This Super.com deal was found by Cheapflights users on 6/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Deal found 6/11![Frontier logo]()
$132
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:40 am
RDU
- ORD
1 stop4h 46m
United Airlines
Deal found 6/10![United Airlines 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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Kiwi.com) |
One-way from | $127 (Kiwi.com) |
Popular in | February |
Cheapest in | December |
Average price | $337 |
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 June 12, 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
Mon 8/10
12:53 pm-4:51 pm
1 stop4h 58m
Chicago O'Hare Intl
Wed 8/12
3:25 pm-9:07 pm
1 stop4h 42m
$250
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Wed 8/12
9:53 am-1:08 pm
1 stop4h 15m
Chicago O'Hare Intl
Mon 8/17
6:40 am-2:20 pm
1 stop6h 40m
$252
Quickest round-trip
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 8/5
6:25 pm-7:20 pm
Nonstop1h 55m
Chicago Midway
Wed 8/12
6:00 pm-8:55 pm
Nonstop1h 55m
$259
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 8/6
5:05 pm-10:15 pm
1 stop6h 10m
Chicago Midway
Mon 8/10
8:50 am-11:50 am
Nonstop2h 00m
$271
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 7/9
9:03 pm-7:00 pm
1 stop22h 57m
Chicago Greater Rockford
Thu 7/16
11:27 am-10:19 am
2 stops21h 52m
$273
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 6/30
1:15 pm-2:45 pm
Nonstop2h 30m
Chicago O'Hare Intl
Sat 7/4
6:55 am-10:08 am
Nonstop2h 13m
$275
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 7/7
5:12 pm-6:42 pm
Nonstop2h 30m
Chicago O'Hare Intl
Tue 7/14
10:48 am-2:01 pm
Nonstop2h 13m
$275
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 8/27
4:50 pm-11:20 pm
2 stops7h 30m
Chicago Midway
Sat 8/29
9:20 am-8:55 pm
2 stops10h 35m
$276
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 7/30
9:03 pm-7:00 pm
1 stop22h 57m
Chicago Greater Rockford
Mon 8/3
7:50 pm-9:25 am
1 stop12h 35m
$277
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Fri 7/3
8:29 pm-9:15 am
1 stop13h 46m
Chicago Greater Rockford
Fri 7/10
7:50 pm-9:00 am
1 stop12h 10m
$279
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 June 12, 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 25% 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 June 12, 2026.
The most flights from DU8 to CHI are scheduled on a Wednesday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 June 8, 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 June 12, 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.
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
Hammond
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 June 12, 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 June 12, 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 June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$299 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$151 | Average$322 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$299 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$351 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$319 | FlexibilityNo cancel fee | On-time63% |