$119+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Aug 23 — Aug 301
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
Cheapest
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 24, 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 24, 2026.
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:58 pm
RDU
- ORD
1 stop6h 10m
Frontier
Sat 8/2912:44 am
ORD
- RDU
1 stop17h 36m
Frontier
Deal found 7/24![Frontier logo]()
$251
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:56 pm
RDU
- MDW
1 stop4h 50m
Frontier
Sun 9/136:25 am
MDW
- RDU
1 stop5h 13m
Frontier
Deal found 7/24![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/116:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Sat 8/151:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 7/23![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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
2 stops24h 47m
Frontier
Tue 8/181:59 pm
ORD
- RDU
1 stop9h 00m
Frontier
Deal found 7/23![Frontier logo]()
$254
This Trip.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/144:20 pm
RDU
- MDW
1 stop6h 38m
Frontier
Tue 9/157:25 am
MDW
- RDU
1 stop6h 42m
Frontier
Deal found 7/23![Frontier logo]()
$254
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Thu 8/2712:09 pm
RDU
- ORD
1 stop5h 39m
American Airlines
Mon 8/318:00 am
ORD
- RDU
1 stop3h 58m
American Airlines
Deal found 7/24![American Airlines logo]()
$255
This Booking.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:47 pm
RDU
- ORD
1 stop22h 03m
Frontier
Sat 8/2912:44 am
ORD
- RDU
1 stop17h 36m
Frontier
Deal found 7/22![Frontier logo]()
$256
This Trip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Thu 9/241:56 pm
RDU
- MDW
1 stop4h 50m
Frontier
Sun 9/2712:03 pm
MDW
- RDU
1 stop11h 26m
Frontier
Deal found 7/24![Frontier logo]()
$256
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:55 am
RDU
- ORD
1 stop8h 40m
Frontier
Sun 9/133:50 pm
ORD
- RDU
1 stop23h 41m
Frontier
Deal found 7/24![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/194:02 pm
RDU
- MDW
1 stop7h 45m
Frontier
Sun 8/236:05 am
MDW
- RDU
1 stop16h 54m
Frontier
Deal found 7/19![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:40 pm
RDU
- ORD
1 stop8h 54m
Frontier
Sun 9/1310:40 pm
ORD
- RDU
1 stop12h 13m
Frontier
Deal found 7/19![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/166:14 pm
RDU
- ORD
1 stop14h 48m
Frontier
Sun 8/237:05 am
ORD
- RDU
1 stop15h 54m
Frontier
Deal found 7/19![Frontier logo]()
$259
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 24, 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 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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
1 stop13h 59m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/286:25 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Mon 8/319:10 am
ORD
- RDU
Nonstop2h 23m
United Airlines
Deal found 7/21![United Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/246:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Sun 9/278:05 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/23![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/275:32 am
RDU
- MDW
1 stop4h 45m
Delta
Mon 8/315:45 pm
MDW
- RDU
1 stop4h 40m
Delta
Deal found 7/23![Delta logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:59 pm
RDU
- RFD
1 stop11h 03m
Multiple Airlines
Sun 10/1110:30 am
RFD
- RDU
2 stops20h 00m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/2610:05 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 8/302:30 pm
ORD
- RDU
Nonstop2h 11m
United Airlines
Deal found 7/24![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/227:30 am
RDU
- MDW
Nonstop1h 50m
Southwest
Sat 8/223:10 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 7/23![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 1/148:00 am
RDU
- MDW
Nonstop2h 00m
Southwest
Mon 1/187:55 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/23![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:10 pm
RDU
- ORD
Nonstop2h 31m
United Airlines
Sun 10/46:25 pm
ORD
- RDU
Nonstop2h 21m
United Airlines
Deal found 7/20![United Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/139:59 pm
RDU
- RFD
1 stop12h 33m
Multiple Airlines
Fri 9/185:05 pm
RFD
- RDU
2 stops30h 12m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:25 am
RDU
- MDW
Nonstop1h 50m
Southwest
Mon 9/146:30 pm
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/23![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/146:15 pm
RDU
- ORD
1 stop6h 42m
Delta
Tue 8/186:25 pm
ORD
- RDU
1 stop5h 17m
Delta
Deal found 7/20![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/136:25 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Mon 8/177:10 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/22![United Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Sun 9/208:05 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/19![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/281:14 pm
RDU
- RFD
1 stop21h 37m
Multiple Airlines
Sat 10/314:53 pm
RFD
- RDU
2 stops39h 12m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/1710:40 am
RDU
- ORD
1 stop4h 47m
United Airlines
Sun 8/2312:50 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 7/19![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Fri 9/186:30 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 7/19![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:59 pm
RDU
- RFD
1 stop11h 53m
Multiple Airlines
Mon 9/215:20 pm
RFD
- RDU
2 stops29h 57m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/47:59 pm
RDU
- ORD
1 stop4h 41m
United Airlines
Mon 9/77:10 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/23![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/127:30 am
RDU
- MDW
Nonstop1h 50m
Southwest
Sun 9/138:05 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/19![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/137:52 pm
RDU
- RFD
1 stop22h 44m
Multiple Airlines
Mon 8/176:26 pm
RFD
- RDU
1 stop14h 26m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/186:00 am
RDU
- ORD
1 stop4h 38m
United Airlines
Sat 8/2212:50 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 7/20![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/67:00 am
RDU
- MDW
Nonstop2h 00m
Southwest
Wed 10/76:10 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 7/21![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:00 pm
RDU
- RFD
1 stop25h 23m
Multiple Airlines
Sun 10/1810:30 am
RFD
- RDU
2 stops12h 47m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/36:00 am
RDU
- ORD
1 stop4h 38m
United Airlines
Mon 9/77:10 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/19![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/106:25 am
RDU
- MDW
1 stop6h 50m
Southwest
Sun 9/137:50 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 7/20![Southwest logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/52:30 pm
RDU
- RFD
2 stops21h 17m
Multiple Airlines
Fri 8/76:26 pm
RFD
- RDU
1 stop13h 50m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/157:59 pm
RDU
- ORD
1 stop4h 41m
United Airlines
Sun 8/1610:50 am
ORD
- RDU
Nonstop2h 17m
United Airlines
Deal found 7/21![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Mon 9/147:55 am
MDW
- RDU
1 stop4h 05m
Southwest
Deal found 7/21![Southwest logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/20![Multiple Airlines logo]()
$344
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated July 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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
1 stop13h 59m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/812:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Mon 8/106:05 am
MDW
- RDU
1 stop15h 30m
Frontier
Deal found 7/19![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/116:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Sat 8/151:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 7/23![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/1211:56 am
RDU
- ORD
1 stop8h 57m
Frontier
Tue 8/181:59 pm
ORD
- RDU
1 stop9h 00m
Frontier
Deal found 7/23![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/136:15 am
RDU
- MDW
1 stop16h 48m
Frontier
Sun 8/166:05 am
MDW
- RDU
1 stop15h 39m
Frontier
Deal found 7/19![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/136:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Sat 8/157:05 am
ORD
- RDU
2 stops11h 06m
Frontier
Deal found 7/22![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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
2 stops24h 47m
Frontier
Tue 8/181:59 pm
ORD
- RDU
1 stop9h 00m
Frontier
Deal found 7/23![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/166:14 pm
RDU
- ORD
1 stop14h 48m
Frontier
Sun 8/237:05 am
ORD
- RDU
1 stop15h 54m
Frontier
Deal found 7/19![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/194:02 pm
RDU
- MDW
1 stop7h 45m
Frontier
Sun 8/236:05 am
MDW
- RDU
1 stop16h 54m
Frontier
Deal found 7/19![Frontier logo]()
$257
This Booking.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:47 pm
RDU
- ORD
1 stop22h 03m
Frontier
Sat 8/2912:44 am
ORD
- RDU
1 stop17h 36m
Frontier
Deal found 7/22![Frontier logo]()
$256
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Thu 8/2712:09 pm
RDU
- ORD
1 stop5h 39m
American Airlines
Mon 8/318:00 am
ORD
- RDU
1 stop3h 58m
American Airlines
Deal found 7/24![American Airlines logo]()
$255
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:58 pm
RDU
- ORD
1 stop6h 10m
Frontier
Sat 8/2912:44 am
ORD
- RDU
1 stop17h 36m
Frontier
Deal found 7/24![Frontier logo]()
$251
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 24, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/191:53 pm
RDU
- ORD
1 stop5h 56m
Delta
Deal found 7/22![Delta logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:14 pm
RDU
- RFD
1 stop22h 51m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/236:00 am
RDU
- MDW
2 stops6h 50m
Southwest
Deal found 7/24![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/2310:11 pm
RDU
- ORD
1 stop10h 42m
Frontier
Deal found 7/22![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/115:01 pm
RDU
- ORD
1 stop16h 01m
Frontier
Deal found 7/22![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/712:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Deal found 7/19![Frontier logo]()
$122
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/175:10 pm
RDU
- ORD
1 stop4h 45m
Delta
Deal found 7/20![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/176:15 pm
RDU
- MDW
1 stop5h 21m
Delta
Deal found 7/20![Delta logo]()
$123
This Frontier deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/201:40 pm
RDU
- ORD
1 stop8h 54m
Frontier
Deal found 7/22![Frontier logo]()
$124
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:25 am
RDU
- MDW
2 stops10h 00m
Southwest
Deal found 7/22![Southwest logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:59 pm
RDU
- ORD
2 stops22h 45m
Frontier
Deal found 7/21![Frontier logo]()
$125
This Trip.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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.
Fri 9/186:35 am
RDU
- MDW
1 stop16h 23m
Frontier
Deal found 7/20![Frontier logo]()
$125
Find flight deals from Durham to Chicago
Keep the following information in mind while searching for Durham to Chicago flight deals. Data was last updated July 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Kiwi.com) |
One-way from | $119 (Delta) |
Popular in | June |
Cheapest in | December |
Average price | $340 |
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 24, 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 - RFD
RDURFD
Raleigh-Durham
Thu 8/6
10:34 pm-7:49 am
1 stop10h 15m
Chicago Greater Rockford
Mon 8/10
6:26 pm-9:25 am
1 stop13h 59m
$259
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Fri 8/28
6:25 am-7:49 am
Nonstop2h 24m
Chicago O'Hare Intl
Mon 8/31
9:10 am-12:33 pm
Nonstop2h 23m
$272
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 10/8
9:59 pm-8:02 am
1 stop11h 03m
Chicago Greater Rockford
Sun 10/11
10:30 am-7:30 am
2 stops20h 00m
$273
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 9/24
6:45 pm-7:40 pm
Nonstop1h 55m
Chicago Midway
Sun 9/27
8:05 am-11:05 am
Nonstop2h 00m
$277
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Wed 8/26
10:05 am-11:29 am
Nonstop2h 24m
Chicago O'Hare Intl
Sun 8/30
2:30 pm-5:41 pm
Nonstop2h 11m
$277
Quickest round-trip
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 8/22
7:30 am-8:20 am
Nonstop1h 50m
Chicago Midway
Sat 8/22
3:10 pm-6:05 pm
Nonstop1h 55m
$277
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 1/14
8:00 am-9:00 am
Nonstop2h 00m
Chicago Midway
Mon 1/18
7:55 am-10:55 am
Nonstop2h 00m
$277
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Mon 9/7
8:25 am-9:15 am
Nonstop1h 50m
Chicago Midway
Mon 9/14
6:30 pm-9:30 pm
Nonstop2h 00m
$277
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 10/3
1:10 pm-2:41 pm
Nonstop2h 31m
Chicago O'Hare Intl
Sun 10/4
6:25 pm-9:46 pm
Nonstop2h 21m
$281
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/16
6:25 pm-7:20 pm
Nonstop1h 55m
Chicago Midway
Sun 9/20
8:05 am-11:05 am
Nonstop2h 00m
$281
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 July 24, 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 24, 2026.
The most flights from DU8 to CHI are scheduled on a Wednesday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Durham to Chicago?
Airfare is typical for this route at the moment.
Durham to Chicago flights typically cost between $244 and $370 in September.The cheapest round-trip price found within the last 5 days was $251 on Multiple Airlines (Sep 14-Sep 15).
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 18, 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 24, 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
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Durham to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Durham to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 24, 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 24, 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$306 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$330 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$167 | Average$326 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$358 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$188 | Average$336 | FlexibilityNo cancel fee | On-time63% |