$49+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Mar 20 — Mar 271
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 August or October, booked 90 days in advance, depart on a Thursday or Friday and return on a Thursday
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 February 18, 2026.
Explore the most affordable flight options available from Durham to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 2026.
This WAYA deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:25 am
RDU
- ORD
1 stop5h 26m
Frontier
Wed 2/256:02 pm
ORD
- RDU
1 stop5h 09m
Frontier
Deal found 2/18![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- ORD
1 stop17h 29m
Frontier
Tue 3/109:28 am
ORD
- RDU
1 stop4h 49m
Frontier
Deal found 2/17![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- ORD
1 stop5h 41m
Multiple Airlines
Mon 3/96:51 pm
ORD
- RDU
1 stop21h 20m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- MDW
1 stop16h 29m
Frontier
Mon 3/96:15 am
MDW
- RDU
1 stop8h 21m
Frontier
Deal found 2/17![Frontier logo]()
$167
This Frontier deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:14 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Sun 5/171:27 pm
ORD
- RDU
1 stop6h 25m
Frontier
Deal found 2/18![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
RDU
- MDW
1 stop17h 19m
Frontier
Sun 4/196:00 am
MDW
- RDU
1 stop25h 46m
Frontier
Deal found 2/16![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/124:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Tue 3/179:28 am
ORD
- RDU
1 stop4h 49m
Frontier
Deal found 2/16![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:07 pm
RDU
- MDW
1 stop7h 12m
Frontier
Tue 3/176:00 am
MDW
- RDU
1 stop8h 17m
Frontier
Deal found 2/15![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:10 pm
RDU
- ORD
2 stops19h 12m
Multiple Airlines
Thu 3/57:00 am
ORD
- RDU
1 stop6h 13m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- MDW
1 stop16h 29m
Frontier
Sat 3/76:00 am
MDW
- RDU
1 stop16h 16m
Frontier
Deal found 2/17![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:10 pm
RDU
- ORD
1 stop6h 29m
Multiple Airlines
Mon 3/96:51 pm
ORD
- RDU
1 stop21h 20m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$171
This CheapOair deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:38 pm
RDU
- MDW
1 stop10h 26m
Frontier
Sun 5/179:14 am
MDW
- RDU
1 stop21h 42m
Frontier
Deal found 2/18![Frontier logo]()
$171
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 February 18, 2026.
Discover carefully curated flight deals from Durham to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 18, 2026.
This United Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:50 pm
RDU
- ORD
1 stop4h 53m
United Airlines
Sat 4/256:15 pm
ORD
- RDU
Nonstop2h 08m
United Airlines
Deal found 2/14![United Airlines logo]()
$171
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:50 pm
RDU
- ORD
1 stop6h 44m
Delta
Sat 5/308:10 am
ORD
- RDU
1 stop4h 26m
Delta
Deal found 2/15![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:45 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Tue 5/56:05 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/14![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:45 am
RDU
- MDW
1 stop15h 22m
Frontier
Sun 4/197:30 am
MDW
- RDU
2 stops39h 45m
Frontier
Deal found 2/14![Frontier logo]()
$185
This United Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:41 am
RDU
- ORD
1 stop4h 47m
United Airlines
Sat 5/1611:00 am
ORD
- RDU
Nonstop2h 09m
United Airlines
Deal found 2/14![United Airlines logo]()
$171
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:45 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Mon 4/272:40 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/16![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:07 pm
RDU
- ORD
1 stop6h 06m
Delta
Sat 5/2311:07 am
ORD
- RDU
1 stop4h 29m
Delta
Deal found 2/14![Delta logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:00 pm
RDU
- RFD
1 stop21h 19m
Multiple Airlines
Sat 5/3010:11 am
RFD
- RDU
1 stop10h 10m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:21 pm
RDU
- ORD
Nonstop2h 34m
United Airlines
Fri 5/159:15 pm
ORD
- RDU
Nonstop2h 15m
United Airlines
Deal found 2/18![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
RDU
- MDW
Nonstop2h 00m
Southwest
Sat 4/183:45 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/16![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:45 am
RDU
- MDW
1 stop3h 58m
Delta
Mon 5/186:36 pm
MDW
- RDU
1 stop3h 50m
Delta
Deal found 2/15![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1110:34 am
RDU
- ORD
1 stop4h 53m
United Airlines
Sun 4/197:00 am
ORD
- RDU
Nonstop2h 06m
United Airlines
Deal found 2/14![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:40 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Sat 5/163:45 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/17![Southwest logo]()
$196
This United Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:50 pm
RDU
- ORD
1 stop4h 53m
United Airlines
Sat 4/188:50 am
ORD
- RDU
Nonstop2h 10m
United Airlines
Deal found 2/14![United Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:20 am
RDU
- MDW
1 stop4h 36m
Delta
Sun 4/196:38 pm
MDW
- RDU
1 stop4h 01m
Delta
Deal found 2/16![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:40 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Thu 4/306:55 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/17![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:15 am
RDU
- MDW
1 stop6h 47m
Delta
Tue 3/176:34 pm
MDW
- RDU
1 stop3h 58m
Delta
Deal found 2/16![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:21 pm
RDU
- ORD
Nonstop2h 34m
United Airlines
Tue 5/56:05 pm
ORD
- RDU
Nonstop2h 08m
United Airlines
Deal found 2/14![United Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:55 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Sun 4/197:40 am
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/14![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:45 am
RDU
- MDW
1 stop3h 58m
Delta
Mon 5/186:36 pm
MDW
- RDU
1 stop3h 50m
Delta
Deal found 2/17![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:00 am
RDU
- ORD
Nonstop2h 31m
United Airlines
Sat 3/286:08 pm
ORD
- RDU
Nonstop2h 00m
United Airlines
Deal found 2/15![United Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:59 pm
RDU
- ORD
Nonstop2h 40m
United Airlines
Sat 5/162:15 pm
ORD
- RDU
Nonstop2h 08m
United Airlines
Deal found 2/17![United Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:46 pm
RDU
- RFD
1 stop15h 01m
Multiple Airlines
Sat 3/215:04 pm
RFD
- RDU
1 stop14h 54m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$519
This Kiwi.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/187:46 pm
RDU
- RFD
1 stop15h 01m
Multiple Airlines
Sat 3/215:04 pm
RFD
- RDU
1 stop14h 54m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:38 pm
RDU
- RFD
1 stop12h 11m
Multiple Airlines
Thu 3/195:50 pm
RFD
- RDU
1 stop14h 18m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$570
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated February 18, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated February 18, 2026 and is based on user searches.
This WAYA deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:25 am
RDU
- ORD
1 stop5h 26m
Frontier
Wed 2/256:02 pm
ORD
- RDU
1 stop5h 09m
Frontier
Deal found 2/18![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- ORD
1 stop17h 29m
Frontier
Tue 3/109:28 am
ORD
- RDU
1 stop4h 49m
Frontier
Deal found 2/17![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- ORD
1 stop5h 41m
Multiple Airlines
Mon 3/96:51 pm
ORD
- RDU
1 stop21h 20m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- MDW
1 stop16h 29m
Frontier
Mon 3/96:15 am
MDW
- RDU
1 stop8h 21m
Frontier
Deal found 2/17![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:10 am
RDU
- MDW
1 stop16h 29m
Frontier
Sat 3/76:00 am
MDW
- RDU
1 stop16h 16m
Frontier
Deal found 2/17![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:10 pm
RDU
- ORD
2 stops29h 03m
Multiple Airlines
Thu 3/57:00 am
ORD
- RDU
1 stop6h 13m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:10 pm
RDU
- ORD
1 stop6h 29m
Multiple Airlines
Mon 3/96:51 pm
ORD
- RDU
1 stop21h 20m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$171
This Frontier deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/124:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Wed 3/189:28 am
ORD
- RDU
1 stop4h 49m
Frontier
Deal found 2/17![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:07 pm
RDU
- MDW
1 stop7h 12m
Frontier
Tue 3/176:00 am
MDW
- RDU
1 stop8h 17m
Frontier
Deal found 2/15![Frontier logo]()
$169
This CheapOair deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1810:38 pm
RDU
- MDW
1 stop20h 06m
Frontier
Tue 3/244:33 pm
MDW
- RDU
1 stop14h 19m
Frontier
Deal found 2/16![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:12 pm
RDU
- MDW
1 stop7h 07m
Frontier
Thu 3/192:41 pm
MDW
- RDU
1 stop8h 30m
Frontier
Deal found 2/16![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/194:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Sun 3/2210:12 pm
ORD
- RDU
1 stop7h 53m
Frontier
Deal found 2/16![Frontier logo]()
$168
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 February 18, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated February 18, 2026.
This Frontier deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/124:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Deal found 2/15![Frontier logo]()
$49
This United Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:30 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Deal found 2/15![United Airlines logo]()
$52
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:55 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Deal found 2/16![Southwest logo]()
$52
This Priceline deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/264:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Deal found 2/17![Frontier logo]()
$53
This Frontier deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/194:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Deal found 2/17![Frontier logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:47 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/16![Frontier logo]()
$57
This Frontier deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:47 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/18![Frontier logo]()
$58
This United Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:00 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Deal found 2/15![United Airlines logo]()
$62
This Expedia deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:11 pm
RDU
- ORD
Nonstop2h 19m
Frontier
Deal found 2/17![Frontier logo]()
$63
This Priceline deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:14 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/16![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:08 pm
RDU
- ORD
1 stop7h 32m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$67
This Mytrip deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:25 pm
RDU
- ORD
1 stop6h 57m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$69
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 February 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Kiwi.com) |
One-way from | $49 (Frontier) |
Popular in | March |
Cheapest in | August |
Average price | $333 |
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 February 18, 2026.
Use the filters below to find and compare flights from Durham to Chicago that are best for you.
Fly from
Durham
Fly to
Chicago
Route
Depart
Return
Price
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Wed 4/22
7:50 pm-11:43 pm
1 stop4h 53m
Chicago O'Hare Intl
Sat 4/25
6:15 pm-9:23 pm
Nonstop2h 08m
$171
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 5/12
10:41 am-2:28 pm
1 stop4h 47m
Chicago O'Hare Intl
Sat 5/16
11:00 am-2:09 pm
Nonstop2h 09m
$171
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 5/23
2:50 pm-8:34 pm
1 stop6h 44m
Chicago O'Hare Intl
Sat 5/30
8:10 am-1:36 pm
1 stop4h 26m
$177
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 5/1
7:45 pm-8:45 pm
Nonstop2h 00m
Chicago Midway
Tue 5/5
6:05 pm-8:55 pm
Nonstop1h 50m
$177
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 4/23
7:45 pm-8:45 pm
Nonstop2h 00m
Chicago Midway
Mon 4/27
2:40 pm-5:30 pm
Nonstop1h 50m
$177
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 5/12
5:21 pm-6:55 pm
Nonstop2h 34m
Chicago O'Hare Intl
Fri 5/15
9:15 pm-12:30 am
Nonstop2h 15m
$177
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 4/18
8:00 am-9:00 am
Nonstop2h 00m
Chicago Midway
Sat 4/18
3:45 pm-6:35 pm
Nonstop1h 50m
$177
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 4/11
10:34 am-2:27 pm
1 stop4h 53m
Chicago O'Hare Intl
Sun 4/19
7:00 am-10:06 am
Nonstop2h 06m
$178
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Thu 4/9
7:50 pm-11:43 pm
1 stop4h 53m
Chicago O'Hare Intl
Sat 4/18
8:50 am-12:00 pm
Nonstop2h 10m
$179
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 4/11
5:45 am-8:07 pm
1 stop15h 22m
Chicago Midway
Sun 4/19
7:30 am-12:15 am
2 stops39h 45m
$185
Showing 1-10 of 55 results
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-ORD
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-MDW
RDU-ORD
RDU-RFD
How far ahead should I book a flight from Durham to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Durham to Chicago. Price data was last updated on February 18, 2026.
To ensure you get the cheapest price possible for a flight from Durham to Chicago, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Durham to Chicago?
Currently, January is the cheapest month in which you can book a flight from Durham to Chicago (average of $49). Flying from Durham to Chicago in April is currently the most expensive (average of $195). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 February 18, 2026.
One of the essential ways to save on airfare from Durham to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 39% on airfare.
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 February 17, 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.
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 February 18, 2026.
The most flights from DU8 to CHI are scheduled on a Monday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from Durham to Chicago?
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 February 18, 2026.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 February 18, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Durham to Chicago by cabin class
Find flights from Durham to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Durham and Chicago flights
Browse other Durham and Chicago flight options. Last updated on February 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Durham to Chicago flights
Consider these flights traveling from Durham to Chicago.
Top 6 airlines flying from Durham to Chicago
Discover the top 6 airlines that operate flights from Durham to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$300 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$149 | Average$317 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$340 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$314 | FlexibilityNo cancel fee | On-time63% |