$118+ Cheap flights from Durham, NC to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Aug 30 — Sep 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 31, 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 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
RDU
- ORD
1 stop15h 03m
Frontier
Sat 8/222:41 pm
ORD
- RDU
2 stops32h 18m
Frontier
Deal found 7/30![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:46 pm
RDU
- RFD
1 stop13h 08m
Multiple Airlines
Wed 11/43:34 pm
RFD
- RDU
1 stop16h 26m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:59 pm
RDU
- MDW
1 stop6h 01m
Delta
Tue 11/311:39 am
MDW
- RDU
1 stop4h 26m
Delta
Deal found 7/31![Delta logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/186:05 am
RDU
- ORD
1 stop15h 03m
Multiple Airlines
Thu 8/277:05 am
ORD
- RDU
2 stops14h 23m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 pm
RDU
- MDW
1 stop7h 45m
Southwest
Tue 9/812:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 7/31![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/256:05 am
RDU
- ORD
1 stop14h 54m
Multiple Airlines
Tue 9/12:41 pm
ORD
- RDU
2 stops17h 17m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/204:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Sat 8/227:40 am
MDW
- RDU
2 stops10h 15m
Southwest
Deal found 7/29![Southwest logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/158:06 pm
RDU
- ORD
2 stops36h 56m
Frontier
Tue 8/188:05 am
ORD
- RDU
1 stop12h 10m
Frontier
Deal found 7/28![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/206:05 am
RDU
- MDW
2 stops15h 26m
Frontier
Sat 8/2211:45 am
MDW
- RDU
1 stop11h 14m
Frontier
Deal found 7/30![Frontier logo]()
$244
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Mon 9/146:00 am
RDU
- ORD
Nonstop2h 31m
American Airlines
Mon 9/216:29 am
ORD
- RDU
1 stop3h 47m
American Airlines
Deal found 7/31![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/146:05 pm
RDU
- MDW
1 stop5h 40m
Southwest
Wed 9/166:00 pm
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/31![Southwest logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/131:56 pm
RDU
- ORD
1 stop5h 27m
Frontier
Tue 9/296:20 am
ORD
- RDU
1 stop5h 18m
Frontier
Deal found 7/29![Frontier logo]()
$246
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 31, 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 31, 2026.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/286:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Tue 9/88:35 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/30![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/281:15 pm
RDU
- ORD
Nonstop2h 31m
United Airlines
Mon 9/77:10 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/26![United Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/65:27 pm
RDU
- RFD
1 stop16h 17m
Multiple Airlines
Fri 10/98:02 pm
RFD
- RDU
1 stop11h 57m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:26 pm
RDU
- ORD
1 stop5h 11m
Delta
Sun 9/275:30 am
ORD
- RDU
1 stop4h 56m
Delta
Deal found 7/29![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/301:25 pm
RDU
- MDW
Nonstop1h 50m
Southwest
Fri 10/25:50 pm
MDW
- RDU
1 stop4h 35m
Southwest
Deal found 7/27![Southwest logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/109:35 pm
RDU
- RFD
1 stop12h 17m
Multiple Airlines
Fri 9/115:05 pm
RFD
- RDU
1 stop14h 54m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/216:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Mon 8/248:50 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/29![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/18:06 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 10/49:05 am
ORD
- RDU
Nonstop2h 23m
United Airlines
Deal found 7/28![United Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/109:35 pm
RDU
- RFD
1 stop12h 17m
Multiple Airlines
Mon 9/145:20 pm
RFD
- RDU
1 stop15h 39m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/2410:13 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 9/279:05 am
ORD
- RDU
Nonstop2h 23m
United Airlines
Deal found 7/26![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/254:20 pm
RDU
- MDW
1 stop7h 05m
Southwest
Mon 9/286:30 pm
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/116:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Fri 9/183:15 pm
MDW
- RDU
1 stop5h 40m
Southwest
Deal found 7/27![Southwest logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/152:30 pm
RDU
- RFD
2 stops21h 17m
Multiple Airlines
Mon 8/176:26 pm
RFD
- RDU
1 stop14h 26m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/171:22 pm
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 9/208:42 am
ORD
- RDU
1 stop4h 25m
United Airlines
Deal found 7/31![United Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/299:57 pm
RDU
- RFD
2 stops22h 09m
Multiple Airlines
Mon 11/25:55 pm
RFD
- RDU
1 stop15h 04m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1010:50 am
RDU
- MDW
2 stops8h 05m
Southwest
Thu 10/152:50 pm
MDW
- RDU
2 stops5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$279
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/1810:05 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 9/2010:50 am
ORD
- RDU
Nonstop2h 17m
United Airlines
Deal found 7/31![United Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/122:30 pm
RDU
- RFD
2 stops21h 17m
Multiple Airlines
Fri 8/146:26 pm
RFD
- RDU
1 stop13h 50m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/34:50 pm
RDU
- MDW
2 stops7h 35m
Southwest
Sun 9/69:30 am
MDW
- RDU
2 stops11h 05m
Southwest
Deal found 7/26![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/286:55 am
RDU
- ORD
1 stop5h 56m
United Airlines
Sun 8/307:15 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/28![United Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/249:35 pm
RDU
- RFD
1 stop12h 17m
Multiple Airlines
Sun 9/273:53 pm
RFD
- RDU
2 stops14h 42m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:13 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sat 10/312:55 pm
ORD
- RDU
Nonstop2h 20m
United Airlines
Deal found 7/27![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 am
RDU
- MDW
1 stop5h 15m
Southwest
Sun 9/271:20 pm
MDW
- RDU
2 stops7h 50m
Southwest
Deal found 7/28![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/46:25 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Mon 9/77:10 am
ORD
- RDU
Nonstop2h 16m
United Airlines
Deal found 7/26![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:55 am
RDU
- MDW
Nonstop2h 00m
Southwest
Sun 10/187:45 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/28![Southwest logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/301:56 pm
RDU
- RFD
2 stops19h 44m
Multiple Airlines
Fri 10/28:02 pm
RFD
- RDU
1 stop11h 57m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/186:56 am
RDU
- ORD
1 stop6h 03m
United Airlines
Thu 8/272:30 pm
ORD
- RDU
Nonstop2h 11m
United Airlines
Deal found 7/31![United Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:25 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Sun 9/206:28 pm
ORD
- RDU
Nonstop2h 21m
United Airlines
Deal found 7/31![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/18:40 am
RDU
- MDW
2 stops5h 45m
Southwest
Sun 10/410:00 am
MDW
- RDU
2 stops6h 45m
Southwest
Deal found 7/28![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/166:25 am
RDU
- ORD
Nonstop2h 24m
United Airlines
Mon 8/176:28 pm
ORD
- RDU
Nonstop2h 21m
United Airlines
Deal found 7/27![United Airlines logo]()
$353
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated July 31, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated July 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/158:06 pm
RDU
- ORD
2 stops36h 56m
Frontier
Tue 8/188:05 am
ORD
- RDU
1 stop12h 10m
Frontier
Deal found 7/28![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/186:05 am
RDU
- ORD
1 stop15h 03m
Multiple Airlines
Thu 8/277:05 am
ORD
- RDU
2 stops14h 23m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$242
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Mon 8/3111:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/31![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
RDU
- ORD
1 stop15h 03m
Frontier
Sat 8/222:41 pm
ORD
- RDU
2 stops32h 18m
Frontier
Deal found 7/30![Frontier logo]()
$241
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Wed 8/196:20 am
RDU
- ORD
1 stop8h 19m
Multiple Airlines
Fri 8/211:59 pm
ORD
- RDU
1 stop9h 00m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/204:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Sat 8/227:40 am
MDW
- RDU
2 stops10h 15m
Southwest
Deal found 7/29![Southwest logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/206:05 am
RDU
- MDW
2 stops15h 26m
Frontier
Sat 8/2211:45 am
MDW
- RDU
1 stop11h 14m
Frontier
Deal found 7/30![Frontier logo]()
$244
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/223:50 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Mon 8/245:30 am
MDW
- RDU
1 stop8h 55m
Southwest
Deal found 7/31![Southwest logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/256:05 am
RDU
- ORD
1 stop14h 54m
Multiple Airlines
Tue 9/12:41 pm
ORD
- RDU
2 stops17h 17m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$243
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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.
Wed 8/265:58 pm
RDU
- ORD
1 stop6h 10m
Frontier
Wed 9/21:59 pm
ORD
- RDU
1 stop9h 00m
Frontier
Deal found 7/29![Frontier logo]()
$248
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/286:55 am
RDU
- ORD
1 stop5h 56m
United Airlines
Tue 9/812:29 pm
ORD
- RDU
Nonstop2h 08m
United Airlines
Deal found 7/29![United Airlines logo]()
$245
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/284:02 pm
RDU
- MDW
1 stop7h 45m
Frontier
Mon 8/3111:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/27![Frontier logo]()
$248
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 31, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/2711:29 am
RDU
- ORD
Nonstop2h 25m
United Airlines
Deal found 7/31![United Airlines logo]()
$118
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/197:20 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Deal found 7/31![Southwest logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/61:56 pm
RDU
- ORD
2 stops16h 42m
Frontier
Deal found 7/30![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/2911:15 am
RDU
- MDW
2 stops9h 05m
Southwest
Deal found 7/28![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/249:35 pm
RDU
- RFD
1 stop12h 17m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
RDU
- ORD
1 stop15h 03m
Frontier
Deal found 7/30![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:54 pm
RDU
- MDW
1 stop20h 04m
Frontier
Deal found 7/28![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/239:59 pm
RDU
- ORD
2 stops23h 06m
Frontier
Deal found 7/31![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:05 am
RDU
- MDW
2 stops15h 26m
Frontier
Deal found 7/30![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/106:35 am
RDU
- ORD
2 stops19h 10m
Frontier
Deal found 7/30![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:56 pm
RDU
- MDW
1 stop4h 50m
Frontier
Deal found 7/30![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:04 pm
RDU
- MDW
2 stops28h 54m
Frontier
Deal found 7/31![Frontier logo]()
$123
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 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Kiwi.com) |
One-way from | $118 (United Airlines) |
Popular in | July |
Cheapest in | December |
Average price | $359 |
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 31, 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
Quickest round-trip
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 8/28
6:45 pm-7:40 pm
Nonstop1h 55m
Chicago Midway
Tue 9/8
8:35 am-11:35 am
Nonstop2h 00m
$249
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/30
1:25 pm-2:15 pm
Nonstop1h 50m
Chicago Midway
Fri 10/2
5:50 pm-11:25 pm
1 stop4h 35m
$249
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 8/21
6:45 pm-7:40 pm
Nonstop1h 55m
Chicago Midway
Mon 8/24
8:50 am-11:50 am
Nonstop2h 00m
$249
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 9/25
4:20 pm-10:25 pm
1 stop7h 05m
Chicago Midway
Mon 9/28
6:30 pm-9:30 pm
Nonstop2h 00m
$259
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Fri 8/28
1:15 pm-2:46 pm
Nonstop2h 31m
Chicago O'Hare Intl
Mon 9/7
7:10 am-10:26 am
Nonstop2h 16m
$263
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 9/11
6:45 pm-7:40 pm
Nonstop1h 55m
Chicago Midway
Fri 9/18
3:15 pm-9:55 pm
1 stop5h 40m
$264
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Tue 10/6
5:27 pm-8:44 am
1 stop16h 17m
Chicago Greater Rockford
Fri 10/9
8:02 pm-8:59 am
1 stop11h 57m
$265
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 9/10
9:35 pm-8:52 am
1 stop12h 17m
Chicago Greater Rockford
Fri 9/11
5:05 pm-8:59 am
1 stop14h 54m
$270
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Thu 9/10
9:35 pm-8:52 am
1 stop12h 17m
Chicago Greater Rockford
Mon 9/14
5:20 pm-9:59 am
1 stop15h 39m
$271
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Thu 10/1
8:06 am-9:30 am
Nonstop2h 24m
Chicago O'Hare Intl
Sun 10/4
9:05 am-12:28 pm
Nonstop2h 23m
$277
Showing 1-10 of 57 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-MDW
RDU-RFD
RDU-ORD
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-MDW
RDU-RFD
RDU-ORD
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 31, 2026.
One of the essential ways to save on airfare from Durham to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 22% on airfare.
Weekly flight availability from Durham to Chicago
Explore weekly flight availability from Durham to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 31, 2026.
The most flights from DU8 to CHI are scheduled on a Thursday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 $205 and $336 in August.The cheapest round-trip price found within the last 5 days was $241 on Frontier (Aug 19-Aug 22).
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 25, 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 31, 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Durham to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 31, 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 31, 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 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$311 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$330 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$168 | Average$327 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$360 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$188 | Average$339 | FlexibilityNo cancel fee | On-time63% |