$122+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jul 5 — Jul 121
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 81 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 Juni 5, 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 Juni 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 7/1610:25 am
RDU
- ORD
2 stops26h 50m
Multiple Airlines
Di 7/215:13 pm
ORD
- RDU
1 stop15h 12m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 5/31. 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.
Do 8/610:25 am
RDU
- ORD
2 stops26h 50m
Multiple Airlines
Di 8/118:05 am
ORD
- RDU
1 stop8h 04m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
So 7/198:56 am
RDU
- ORD
1 stop28h 19m
Multiple Airlines
Di 7/215:13 pm
ORD
- RDU
1 stop14h 47m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mi 7/222:31 pm
RDU
- ORD
1 stop9h 39m
Multiple Airlines
Mo 7/278:05 am
ORD
- RDU
2 stops26h 10m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sa 8/812:04 pm
RDU
- ORD
1 stop8h 49m
Frontier
Sa 8/155:30 pm
ORD
- RDU
2 stops28h 14m
Frontier
Deal found 6/4![Frontier logo]()
$246
This Expedia deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Mi 7/1511:56 am
RDU
- MDW
1 stop11h 07m
Frontier
Di 7/2112:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/4![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Fr 6/265:07 pm
RDU
- RFD
1 stop17h 10m
Multiple Airlines
Mo 6/297:48 pm
RFD
- RDU
1 stop12h 31m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Di 6/3012:54 pm
RDU
- ORD
1 stop20h 09m
Frontier
Mi 7/81:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/4![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Di 7/146:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Sa 7/1812:11 pm
MDW
- RDU
1 stop10h 52m
Frontier
Deal found 6/5![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mi 7/111:50 am
RDU
- ORD
1 stop9h 00m
Frontier
Di 7/78:05 am
ORD
- RDU
1 stop8h 04m
Frontier
Deal found 6/2![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sa 7/186:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Di 7/2112:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/4![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mo 7/1312:04 pm
RDU
- ORD
1 stop20h 49m
Multiple Airlines
Mi 7/155:13 pm
ORD
- RDU
1 stop14h 47m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$249
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 Juni 5, 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 Juni 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Fr 6/265:07 pm
RDU
- RFD
1 stop17h 10m
Multiple Airlines
Mo 6/297:48 pm
RFD
- RDU
1 stop12h 31m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Di 7/144:25 pm
RDU
- MDW
1 stop4h 10m
Southwest
Di 7/216:10 pm
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/3![Southwest logo]()
$285
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
So 7/198:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Di 7/2110:48 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/4![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Di 7/149:54 am
RDU
- MDW
1 stop3h 44m
Delta
Do 7/236:00 am
MDW
- RDU
1 stop4h 35m
Delta
Deal found 6/4![Delta logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 7/99:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Mo 7/137:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Do 8/1310:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Mo 8/176:26 pm
RFD
- RDU
1 stop14h 34m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Mi 7/228:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Fr 7/246:25 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 6/3![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mi 7/221:30 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Mo 7/275:00 am
MDW
- RDU
1 stop6h 05m
Southwest
Deal found 6/2![Southwest logo]()
$316
This United Airlines deal was found by Cheapflights users on 5/31. 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.
Di 7/2110:59 am
RDU
- ORD
Nonstop2h 30m
United Airlines
So 7/266:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 5/31![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sa 7/45:33 am
RDU
- ORD
1 stop6h 02m
Delta
Sa 7/45:22 pm
ORD
- RDU
1 stop5h 06m
Delta
Deal found 6/4![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Mi 7/221:50 pm
RDU
- MDW
1 stop7h 50m
Southwest
Do 7/232:45 pm
MDW
- RDU
2 stops6h 40m
Southwest
Deal found 6/5![Southwest logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Di 6/1610:22 pm
RDU
- RFD
1 stop11h 55m
Multiple Airlines
Mi 6/174:42 pm
RFD
- RDU
1 stop16h 01m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Fr 7/177:59 pm
RDU
- ORD
1 stop4h 54m
Delta
Fr 7/245:18 pm
ORD
- RDU
1 stop5h 07m
Delta
Deal found 6/4![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Do 7/98:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
So 7/126:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/3![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Fr 7/31:40 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Fr 7/36:55 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 6/2![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Fr 7/38:29 pm
RDU
- RFD
1 stop13h 46m
Multiple Airlines
Mo 7/67:50 pm
RFD
- RDU
1 stop13h 10m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Sa 7/1810:00 am
RDU
- ORD
Nonstop2h 26m
United Airlines
So 7/196:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/2![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mo 7/137:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Do 7/167:40 am
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/2![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Mi 7/156:45 am
RDU
- MDW
2 stops7h 50m
Southwest
Sa 7/188:00 am
MDW
- RDU
2 stops13h 20m
Southwest
Deal found 6/5![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Sa 7/46:00 am
RDU
- ORD
1 stop7h 06m
United Airlines
Sa 7/1110:48 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/1![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Sa 8/86:40 am
RDU
- MDW
2 stops8h 30m
Southwest
Fr 8/148:15 am
MDW
- RDU
2 stops6h 55m
Southwest
Deal found 6/3![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 7/910:32 am
RDU
- ORD
1 stop4h 57m
United Airlines
Mo 7/132:13 pm
ORD
- RDU
Nonstop2h 14m
United Airlines
Deal found 6/2![United Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sa 7/182:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Mo 7/207:50 pm
RFD
- RDU
1 stop13h 10m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 5/31. 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.
Do 8/64:50 pm
RDU
- MDW
2 stops7h 30m
Southwest
Mo 8/102:35 pm
MDW
- RDU
2 stops6h 25m
Southwest
Deal found 5/31![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Fr 7/107:45 pm
RDU
- ORD
1 stop4h 46m
United Airlines
Mo 7/136:25 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 6/5![United Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
So 6/2110:22 pm
RDU
- RFD
1 stop21h 41m
Multiple Airlines
Fr 6/267:48 pm
RFD
- RDU
1 stop12h 31m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Fr 7/247:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Mo 7/2711:55 am
MDW
- RDU
1 stop6h 10m
Southwest
Deal found 6/2![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 6/258:30 pm
RDU
- RFD
1 stop12h 15m
Multiple Airlines
Fr 6/267:48 pm
RFD
- RDU
1 stop12h 31m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Do 7/1610:59 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Mi 7/228:40 am
ORD
- RDU
1 stop4h 28m
United Airlines
Deal found 6/4![United Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Di 6/1610:22 pm
RDU
- RFD
1 stop11h 55m
Multiple Airlines
Fr 6/197:53 pm
RFD
- RDU
1 stop12h 07m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$400
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated Juni 5, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated Juni 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Fr 6/265:07 pm
RDU
- RFD
1 stop17h 10m
Multiple Airlines
Mo 6/297:48 pm
RFD
- RDU
1 stop12h 31m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Di 6/3012:54 pm
RDU
- ORD
1 stop20h 09m
Frontier
Mi 7/81:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/4![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mi 7/111:50 am
RDU
- ORD
1 stop9h 00m
Frontier
Di 7/78:05 am
ORD
- RDU
1 stop8h 04m
Frontier
Deal found 6/2![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 7/99:03 pm
RDU
- RFD
1 stop22h 57m
Multiple Airlines
Mo 7/137:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mo 7/1312:04 pm
RDU
- ORD
1 stop20h 49m
Multiple Airlines
Mi 7/155:13 pm
ORD
- RDU
1 stop14h 47m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$249
This Frontier deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Di 7/146:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Sa 7/1812:11 pm
MDW
- RDU
1 stop10h 52m
Frontier
Deal found 6/5![Frontier logo]()
$247
This Expedia deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Mi 7/1511:56 am
RDU
- MDW
1 stop11h 07m
Frontier
Di 7/2112:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/4![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 7/1610:25 am
RDU
- ORD
2 stops26h 50m
Multiple Airlines
Di 7/215:13 pm
ORD
- RDU
1 stop15h 12m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sa 7/186:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Di 7/2112:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/4![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
So 7/198:56 am
RDU
- ORD
1 stop28h 19m
Multiple Airlines
Di 7/215:13 pm
ORD
- RDU
1 stop14h 47m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mi 7/222:31 pm
RDU
- ORD
1 stop9h 39m
Multiple Airlines
Mo 7/278:05 am
ORD
- RDU
2 stops26h 10m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Mi 7/225:29 pm
RDU
- ORD
1 stop6h 41m
Frontier
Di 8/49:34 pm
ORD
- RDU
2 stops24h 01m
Frontier
Deal found 6/3![Frontier logo]()
$250
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 Juni 5, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated Juni 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Di 7/2111:55 am
RDU
- ORD
2 stops25h 20m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$122
This Super.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Mi 7/226:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Deal found 6/1![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Di 7/286:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Deal found 6/1![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Mi 7/225:29 pm
RDU
- ORD
1 stop6h 41m
Frontier
Deal found 6/1![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Mo 7/66:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Deal found 6/3![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Fr 7/246:15 am
RDU
- ORD
1 stop26h 38m
Frontier
Deal found 6/4![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Mo 8/316:15 am
RDU
- MDW
1 stop5h 54m
Frontier
Deal found 6/4![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Do 8/137:05 am
RDU
- ORD
2 stops13h 48m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$127
This Trip.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Di 6/306:15 am
RDU
- MDW
1 stop5h 57m
Frontier
Deal found 6/1![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Mo 8/1012:26 pm
RDU
- ORD
1 stop9h 26m
Frontier
Deal found 6/5![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Do 7/91:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Deal found 6/2![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Mo 6/2912:10 pm
RDU
- ORD
1 stop20h 53m
Frontier
Deal found 6/5![Frontier logo]()
$129
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 Juni 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Kiwi.com) |
One-way from | $122 (Kiwi.com) |
Popular in | February |
Cheapest in | December |
Average price | $307 |
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 Juni 5, 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
Fr 6/26
5:07 pm-9:17 am
1 stop17h 10m
Chicago Greater Rockford
Mo 6/29
7:48 pm-9:19 am
1 stop12h 31m
$246
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Do 7/9
9:03 pm-7:00 pm
1 stop22h 57m
Chicago Greater Rockford
Mo 7/13
7:50 pm-9:25 am
1 stop12h 35m
$250
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Do 8/13
10:34 pm-7:49 am
1 stop10h 15m
Chicago Greater Rockford
Mo 8/17
6:26 pm-10:00 am
1 stop14h 34m
$269
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Di 7/14
4:25 pm-7:35 pm
1 stop4h 10m
Chicago Midway
Di 7/21
6:10 pm-9:10 pm
Nonstop2h 00m
$285
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
So 7/19
8:05 am-9:31 am
Nonstop2h 26m
Chicago O'Hare Intl
Di 7/21
10:48 am-2:01 pm
Nonstop2h 13m
$306
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Mi 7/22
8:05 am-9:31 am
Nonstop2h 26m
Chicago O'Hare Intl
Fr 7/24
6:25 pm-9:37 pm
Nonstop2h 12m
$306
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Mi 7/22
1:30 pm-2:30 pm
Nonstop2h 00m
Chicago Midway
Mo 7/27
5:00 am-12:05 pm
1 stop6h 05m
$316
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Di 7/21
10:59 am-12:29 pm
Nonstop2h 30m
Chicago O'Hare Intl
So 7/26
6:55 am-10:08 am
Nonstop2h 13m
$317
RaleighChicago
RDU - RFD
RDURFD
Raleigh-Durham
Di 6/16
10:22 pm-9:17 am
1 stop11h 55m
Chicago Greater Rockford
Mi 6/17
4:42 pm-9:43 am
1 stop16h 01m
$318
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Di 7/14
9:54 am-12:38 pm
1 stop3h 44m
Chicago Midway
Do 7/23
6:00 am-11:35 am
1 stop4h 35m
$326
Showing 1-10 of 59 resultsSorted by cheapest first
Best time to book a flight from Durham to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Durham with our price prediction graph.
RDU-ORD
RDU-MDW
RDU-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Durham to Chicago
DU8-CHI
RDU-ORD
RDU-MDW
RDU-RFD
What is the cheapest time of day to fly from DU8 to CHI?
Find hourly flight availability from Durham to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated Juni 5, 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 26% 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 Juni 5, 2026.
The most flights from DU8 to CHI are scheduled on a Friday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 May 30, 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 Juni 5, 2026.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
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
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 Juni 5, 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 Juni 5, 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 Juni 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$195 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$299 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$151 | Average$321 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$299 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$173 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$314 | FlexibilityNo cancel fee | On-time63% |