$131+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jul 18 — Jul 251
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 18, 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 18, 2026.
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:13 am
RDU
- ORD
1 stop6h 33m
American Airlines
Tue 7/148:18 am
ORD
- RDU
Nonstop2h 20m
American Airlines
Deal found 6/16![American Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:20 pm
RDU
- MDW
1 stop3h 55m
Southwest
Tue 8/46:00 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/15![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:59 am
RDU
- ORD
2 stops26h 16m
Multiple Airlines
Fri 7/311:50 pm
ORD
- RDU
1 stop9h 14m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:20 am
RDU
- MDW
Nonstop1h 50m
Southwest
Tue 9/112:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 6/14![Southwest logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:29 pm
RDU
- ORD
1 stop6h 41m
Frontier
Tue 7/218:05 am
ORD
- RDU
1 stop8h 04m
Frontier
Deal found 6/14![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 8/1011:06 am
MDW
- RDU
1 stop10h 29m
Frontier
Deal found 6/16![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:04 pm
RDU
- ORD
1 stop8h 49m
Frontier
Mon 7/131:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/16![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Sat 8/811:06 am
MDW
- RDU
1 stop11h 58m
Frontier
Deal found 6/16![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:35 am
RDU
- ORD
1 stop6h 27m
Frontier
Wed 9/302:03 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/15![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/84:05 pm
RDU
- MDW
1 stop6h 53m
Frontier
Wed 10/1412:03 pm
MDW
- RDU
1 stop11h 14m
Frontier
Deal found 6/15![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Sun 8/1611:37 am
RFD
- RDU
2 stops21h 42m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:14 pm
RDU
- ORD
1 stop14h 39m
Frontier
Thu 7/237:05 am
ORD
- RDU
1 stop15h 59m
Frontier
Deal found 6/17![Frontier logo]()
$252
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 18, 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 18, 2026.
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:15 pm
RDU
- ORD
Nonstop2h 31m
United Airlines
Wed 8/269:10 am
ORD
- RDU
Nonstop2h 23m
United Airlines
Deal found 6/15![United Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:25 pm
RDU
- MDW
Nonstop1h 50m
Southwest
Sat 8/227:40 am
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/17![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:59 pm
RDU
- ORD
1 stop4h 18m
Delta
Wed 8/2610:33 am
ORD
- RDU
1 stop4h 30m
Delta
Deal found 6/14![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Mon 8/176:26 pm
RFD
- RDU
1 stop14h 34m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:59 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Tue 7/76:25 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 6/16![United Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/71:15 pm
RDU
- MDW
1 stop6h 15m
Southwest
Wed 7/88:20 am
MDW
- RDU
1 stop3h 50m
Southwest
Deal found 6/13![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:15 pm
RDU
- MDW
1 stop5h 21m
Delta
Wed 8/2610:54 am
MDW
- RDU
1 stop4h 09m
Delta
Deal found 6/14![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
RDU
- ORD
1 stop6h 08m
United Airlines
Tue 9/1510:50 am
ORD
- RDU
Nonstop2h 17m
United Airlines
Deal found 6/15![United Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:29 pm
RDU
- RFD
1 stop13h 46m
Multiple Airlines
Thu 7/1611:27 am
RFD
- RDU
2 stops21h 52m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:50 pm
RDU
- MDW
Nonstop2h 05m
Southwest
Wed 7/83:10 pm
MDW
- RDU
1 stop6h 10m
Southwest
Deal found 6/15![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:55 am
RDU
- ORD
1 stop6h 04m
United Airlines
Sat 8/222:30 pm
ORD
- RDU
Nonstop2h 11m
United Airlines
Deal found 6/17![United Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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
Mon 8/106:26 pm
RFD
- RDU
2 stops27h 18m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:32 am
RDU
- ORD
1 stop6h 10m
Delta
Wed 8/128:05 am
ORD
- RDU
1 stop6h 58m
Delta
Deal found 6/14![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:00 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Fri 7/246:55 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/17![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/309:53 am
RDU
- ORD
1 stop4h 15m
Delta
Wed 9/26:40 am
ORD
- RDU
1 stop5h 05m
Delta
Deal found 6/17![Delta logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 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 6/13![Multiple Airlines logo]()
$308
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Fri 7/2410:48 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/17![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:00 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Tue 8/46:00 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/16![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:59 pm
RDU
- ORD
1 stop4h 18m
Delta
Fri 8/146:40 am
ORD
- RDU
1 stop5h 05m
Delta
Deal found 6/17![Delta logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:29 pm
RDU
- RFD
1 stop13h 46m
Multiple Airlines
Wed 7/84:47 pm
RFD
- RDU
1 stop15h 12m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 8/116:55 am
RDU
- ORD
1 stop6h 04m
United Airlines
Fri 8/149:00 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 6/13![United Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:25 pm
RDU
- MDW
1 stop3h 55m
Southwest
Fri 9/412:50 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/16![Southwest logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/239:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Thu 7/3011:27 am
RFD
- RDU
2 stops19h 44m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Sun 7/266:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/17![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:30 am
RDU
- MDW
Nonstop1h 50m
Southwest
Sun 8/98:05 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/14![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:22 pm
RDU
- RFD
1 stop11h 51m
Multiple Airlines
Fri 7/107:50 pm
RFD
- RDU
1 stop12h 26m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:15 am
RDU
- MDW
2 stops6h 50m
Southwest
Mon 7/205:00 am
MDW
- RDU
1 stop6h 05m
Southwest
Deal found 6/17![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
RDU
- ORD
1 stop4h 36m
United Airlines
Thu 7/239:10 am
ORD
- RDU
Nonstop2h 23m
United Airlines
Deal found 6/17![United Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 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 6/13![Multiple Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:45 pm
RDU
- MDW
2 stops6h 20m
Southwest
Fri 8/149:00 am
MDW
- RDU
1 stop4h 00m
Southwest
Deal found 6/13![Southwest logo]()
$312
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated June 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:13 am
RDU
- ORD
1 stop6h 33m
American Airlines
Tue 7/148:18 am
ORD
- RDU
Nonstop2h 20m
American Airlines
Deal found 6/16![American Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:14 pm
RDU
- ORD
Nonstop2h 57m
American Airlines
Mon 8/108:40 pm
ORD
- RDU
Nonstop2h 02m
American Airlines
Deal found 6/15![American Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/85:29 pm
RDU
- ORD
1 stop6h 41m
Frontier
Tue 7/141:50 pm
ORD
- RDU
1 stop17h 21m
Frontier
Deal found 6/18![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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
- MDW
1 stop16h 48m
Frontier
Wed 7/1512:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:04 pm
RDU
- ORD
1 stop8h 49m
Frontier
Mon 7/131:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/16![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:04 pm
RDU
- ORD
1 stop8h 49m
Frontier
Sat 7/181:50 pm
ORD
- RDU
1 stop9h 13m
Frontier
Deal found 6/17![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/126:14 pm
RDU
- MDW
1 stop17h 53m
Frontier
Wed 7/1512:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$253
This Expedia deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Sat 7/1812:11 pm
MDW
- RDU
1 stop10h 52m
Frontier
Deal found 6/16![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:29 pm
RDU
- ORD
1 stop6h 41m
Frontier
Tue 7/218:05 am
ORD
- RDU
1 stop8h 04m
Frontier
Deal found 6/14![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:56 am
RDU
- ORD
1 stop28h 19m
Frontier
Thu 7/231:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/15![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:59 am
RDU
- ORD
2 stops26h 16m
Multiple Airlines
Fri 7/311:50 pm
ORD
- RDU
1 stop9h 14m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:20 pm
RDU
- MDW
1 stop3h 55m
Southwest
Tue 8/46:00 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/15![Southwest logo]()
$247
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 18, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1610:25 am
RDU
- ORD
2 stops26h 50m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/152:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$132
This Super.com deal was found by Cheapflights users on 6/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:26 pm
RDU
- ORD
1 stop9h 26m
Frontier
Deal found 6/13![Frontier logo]()
$133
This Super.com deal was found by Cheapflights users on 6/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Deal found 6/13![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/161:30 pm
RDU
- ORD
1 stop7h 17m
Frontier
Deal found 6/18![Frontier logo]()
$134
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Deal found 6/17![Frontier logo]()
$134
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:05 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Deal found 6/16![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Deal found 6/16![Southwest logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:59 am
RDU
- ORD
2 stops26h 16m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$137
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/48:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Deal found 6/18![United Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:14 pm
RDU
- RFD
2 stops41h 23m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$138
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 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (American Airlines) |
One-way from | $131 (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 18, 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 8/24
1:15 pm-2:46 pm
Nonstop2h 31m
Chicago O'Hare Intl
Wed 8/26
9:10 am-12:33 pm
Nonstop2h 23m
$253
Quickest round-trip
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Tue 8/18
1:25 pm-2:15 pm
Nonstop1h 50m
Chicago Midway
Sat 8/22
7:40 am-10:35 am
Nonstop1h 55m
$253
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 7/4
10:59 am-12:29 pm
Nonstop2h 30m
Chicago O'Hare Intl
Tue 7/7
6:25 pm-9:37 pm
Nonstop2h 12m
$256
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Wed 8/19
12:59 pm-4:17 pm
1 stop4h 18m
Chicago O'Hare Intl
Wed 8/26
10:33 am-4:03 pm
1 stop4h 30m
$257
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Tue 7/7
1:15 pm-6:30 pm
1 stop6h 15m
Chicago Midway
Wed 7/8
8:20 am-1:10 pm
1 stop3h 50m
$257
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 8/19
6:15 pm-10:36 pm
1 stop5h 21m
Chicago Midway
Wed 8/26
10:54 am-4:03 pm
1 stop4h 09m
$257
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 9/12
7:00 am-12:08 pm
1 stop6h 08m
Chicago O'Hare Intl
Tue 9/15
10:50 am-2:07 pm
Nonstop2h 17m
$259
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 8/18
6:55 am-11:59 am
1 stop6h 04m
Chicago O'Hare Intl
Sat 8/22
2:30 pm-5:41 pm
Nonstop2h 11m
$259
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 7/4
3:50 pm-4:55 pm
Nonstop2h 05m
Chicago Midway
Wed 7/8
3:10 pm-10:20 pm
1 stop6h 10m
$266
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 8/13
10:34 pm-7:49 am
1 stop10h 15m
Chicago Greater Rockford
Mon 8/17
6:26 pm-10:00 am
1 stop14h 34m
$271
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-RFD
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-ORD
RDU-RFD
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 June 18, 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 18, 2026.
The most flights from DU8 to CHI are scheduled on a Thursday (39 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 13, 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 18, 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.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
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 18, 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 18, 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 18, 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$152 | Average$323 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$299 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$173 | Average$352 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$321 | FlexibilityNo cancel fee | On-time63% |