$39+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Mar 14 — Mar 211
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 12, 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 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/266:55 pm
RDU
- ORD
2 stops27h 18m
Multiple Airlines
Wed 3/256:01 pm
ORD
- RDU
1 stop22h 28m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/166:00 am
RDU
- ORD
1 stop5h 44m
Frontier
Sat 4/184:28 pm
ORD
- RDU
1 stop6h 47m
Frontier
Deal found 2/9![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/154:07 pm
RDU
- MDW
1 stop7h 12m
Frontier
Sat 5/162:20 pm
MDW
- RDU
1 stop8h 55m
Frontier
Deal found 2/9![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/186:14 pm
RDU
- ORD
1 stop7h 26m
Multiple Airlines
Mon 3/26:40 am
ORD
- RDU
1 stop11h 12m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$161
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/179:47 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Sun 4/191:12 pm
ORD
- RDU
Nonstop2h 07m
Frontier
Deal found 2/9![Frontier logo]()
$162
This Trip.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:10 pm
RDU
- MDW
1 stop6h 19m
Frontier
Thu 2/266:15 am
MDW
- RDU
1 stop6h 30m
Frontier
Deal found 2/8![Frontier logo]()
$162
This CheapOair deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
Fri 3/206:25 pm
RDU
- ORD
1 stop6h 57m
Spirit Airlines
Mon 3/236:01 pm
ORD
- RDU
1 stop22h 28m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$164
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/266:10 am
RDU
- ORD
1 stop5h 41m
Frontier
Mon 3/26:19 pm
ORD
- RDU
Nonstop2h 03m
Frontier
Deal found 2/9![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/266:10 am
RDU
- MDW
1 stop11h 06m
Frontier
Fri 2/276:00 am
MDW
- RDU
2 stops11h 52m
Frontier
Deal found 2/8![Frontier logo]()
$165
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Thu 3/56:08 pm
RDU
- ORD
1 stop7h 32m
Spirit Airlines
Sun 3/87:23 pm
ORD
- RDU
2 stops20h 48m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/246:25 am
RDU
- ORD
1 stop11h 27m
Multiple Airlines
Wed 2/257:00 am
ORD
- RDU
2 stops16h 11m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$167
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/224:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Thu 3/2612:34 pm
ORD
- RDU
Nonstop2h 03m
Frontier
Deal found 2/9![Frontier logo]()
$168
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 12, 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 12, 2026.
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/174:07 pm
RDU
- MDW
1 stop7h 12m
Frontier
Sun 4/192:20 pm
MDW
- RDU
1 stop8h 55m
Frontier
Deal found 2/9![Frontier logo]()
$160
This JetBlue deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:15 am
RDU
- ORD
1 stop6h 33m
JetBlue
Mon 3/96:04 am
ORD
- RDU
1 stop7h 43m
JetBlue
Deal found 2/9![JetBlue logo]()
$174
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/77:45 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Mon 5/116:55 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/9![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/511:00 am
ORD
- RDU
Nonstop2h 09m
United Airlines
Deal found 2/11![United Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/165:51 pm
RDU
- ORD
1 stop16h 24m
Multiple Airlines
Tue 5/195:34 pm
ORD
- RDU
2 stops15h 25m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/41:01 pm
RDU
- MDW
1 stop5h 36m
Delta
Sat 3/79:34 am
MDW
- RDU
1 stop5h 42m
Delta
Deal found 2/8![Delta logo]()
$210
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/134:48 pm
RDU
- ORD
Nonstop2h 46m
American Airlines
Mon 5/186:00 pm
ORD
- RDU
Nonstop2h 17m
American Airlines
Deal found 2/11![American Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/266:10 am
RDU
- MDW
1 stop11h 06m
Frontier
Fri 2/276:00 am
MDW
- RDU
2 stops11h 52m
Frontier
Deal found 2/8![Frontier logo]()
$165
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/247:45 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Sun 4/267:40 am
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/9![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/156:40 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Fri 4/176:55 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/9![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/118:22 am
RDU
- ORD
Nonstop2h 28m
United Airlines
Wed 3/182:15 pm
ORD
- RDU
Nonstop2h 02m
United Airlines
Deal found 2/9![United Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/175:15 pm
RDU
- ORD
Nonstop2h 36m
United Airlines
Wed 3/188:50 am
ORD
- RDU
1 stop4h 14m
United Airlines
Deal found 2/10![United Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/217:50 pm
RDU
- ORD
1 stop4h 53m
United Airlines
Wed 4/2210:50 am
ORD
- RDU
Nonstop2h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/256:40 pm
RDU
- MDW
1 stop4h 15m
Southwest
Wed 4/17:45 am
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/8![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/249:20 am
RDU
- MDW
1 stop6h 15m
Southwest
Wed 3/256:15 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/9![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:00 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Tue 7/212:07 pm
ORD
- RDU
Nonstop2h 14m
United Airlines
Deal found 2/8![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/306:10 am
RDU
- MDW
1 stop9h 20m
Southwest
Sun 5/37:40 am
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 2/10![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/2110:22 am
RDU
- ORD
Nonstop2h 28m
United Airlines
Tue 3/246:08 pm
ORD
- RDU
Nonstop2h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/146:40 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Thu 4/165:50 pm
MDW
- RDU
1 stop4h 20m
Southwest
Deal found 2/11![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/2810:12 am
RDU
- ORD
Nonstop2h 28m
United Airlines
Wed 4/14:20 pm
ORD
- RDU
1 stop6h 24m
United Airlines
Deal found 2/10![United Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:29 pm
RDU
- RFD
1 stop13h 46m
Multiple Airlines
Mon 7/67:50 pm
RFD
- RDU
1 stop13h 10m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/246:00 am
RDU
- ORD
2 stops7h 50m
Southwest
Wed 3/252:40 pm
ORD
- RDU
2 stops7h 15m
Southwest
Deal found 2/9![Southwest logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/76:30 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Mon 3/97:10 am
ORD
- RDU
Nonstop1h 58m
United Airlines
Deal found 2/9![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/87:46 pm
RDU
- RFD
1 stop15h 01m
Multiple Airlines
Sun 4/1210:37 am
RFD
- RDU
1 stop7h 07m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/229:49 pm
RDU
- RFD
1 stop11h 43m
Multiple Airlines
Thu 2/265:52 pm
RFD
- RDU
1 stop14h 16m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/11![Multiple Airlines logo]()
$589
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated February 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/186:14 pm
RDU
- ORD
1 stop7h 26m
Multiple Airlines
Mon 3/26:40 am
ORD
- RDU
1 stop11h 12m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$161
This Trip.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:10 pm
RDU
- MDW
1 stop6h 19m
Frontier
Thu 2/266:15 am
MDW
- RDU
1 stop6h 30m
Frontier
Deal found 2/8![Frontier logo]()
$162
This Super.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Tue 2/246:25 am
RDU
- ORD
1 stop5h 26m
Frontier
Thu 2/264:42 pm
ORD
- RDU
1 stop6h 28m
Frontier
Deal found 2/9![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/246:25 am
RDU
- ORD
1 stop11h 27m
Multiple Airlines
Wed 2/257:00 am
ORD
- RDU
2 stops16h 11m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/266:55 pm
RDU
- ORD
2 stops27h 18m
Multiple Airlines
Wed 3/256:01 pm
ORD
- RDU
1 stop22h 28m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/266:10 am
RDU
- ORD
1 stop5h 41m
Frontier
Mon 3/26:19 pm
ORD
- RDU
Nonstop2h 03m
Frontier
Deal found 2/9![Frontier logo]()
$165
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Thu 3/56:08 pm
RDU
- ORD
1 stop7h 32m
Spirit Airlines
Sun 3/87:23 pm
ORD
- RDU
2 stops20h 48m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/910:38 pm
RDU
- MDW
2 stops15h 24m
Multiple Airlines
Wed 3/116:05 am
MDW
- RDU
1 stop8h 12m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$169
This Trip.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/104:12 pm
RDU
- MDW
1 stop5h 42m
Frontier
Tue 3/176:00 am
MDW
- RDU
1 stop8h 17m
Frontier
Deal found 2/10![Frontier logo]()
$168
This CheapOair deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
Fri 3/206:25 pm
RDU
- ORD
1 stop6h 57m
Spirit Airlines
Mon 3/236:01 pm
ORD
- RDU
1 stop22h 28m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$164
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/224:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Thu 3/2612:34 pm
ORD
- RDU
Nonstop2h 03m
Frontier
Deal found 2/9![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/254:12 pm
RDU
- ORD
1 stop7h 27m
Frontier
Sun 3/2912:34 pm
ORD
- RDU
Nonstop2h 03m
Frontier
Deal found 2/10![Frontier logo]()
$169
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 12, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/2310:07 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Deal found 2/9![Frontier logo]()
$39
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Fri 2/2710:07 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Deal found 2/9![Frontier logo]()
$40
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/75:14 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/10![Frontier logo]()
$41
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/235:14 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/9![Frontier logo]()
$56
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/49:47 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/10![Frontier logo]()
$57
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:47 pm
RDU
- ORD
Nonstop2h 29m
Frontier
Deal found 2/9![Frontier logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/13:30 pm
RDU
- MDW
1 stop25h 43m
Frontier
Deal found 2/10![Frontier logo]()
$60
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Wed 3/46:08 pm
RDU
- ORD
1 stop7h 32m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$61
This Trip.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:10 pm
RDU
- MDW
1 stop6h 19m
Frontier
Deal found 2/10![Frontier logo]()
$61
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Tue 4/76:25 pm
RDU
- ORD
1 stop6h 57m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$62
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/147:05 pm
RDU
- MDW
Nonstop2h 05m
Southwest
Deal found 2/9![Southwest logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/124:22 pm
RDU
- ORD
Nonstop2h 30m
Frontier
Deal found 2/10![Frontier logo]()
$63
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (Kiwi.com) |
One-way from | $39 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $330 |
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 12, 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 - MDW
RDUMDW
Raleigh-Durham
Fri 4/17
4:07 pm-10:19 pm
1 stop7h 12m
Chicago Midway
Sun 4/19
2:20 pm-12:15 am
1 stop8h 55m
$160
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 2/26
6:10 am-4:16 pm
1 stop11h 06m
Chicago Midway
Fri 2/27
6:00 am-6:52 pm
2 stops11h 52m
$165
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Fri 3/6
6:15 am-11:48 am
1 stop6h 33m
Chicago O'Hare Intl
Mon 3/9
6:04 am-2:47 pm
1 stop7h 43m
$174
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 5/7
7:45 pm-8:45 pm
Nonstop2h 00m
Chicago Midway
Mon 5/11
6:55 pm-9:45 pm
Nonstop1h 50m
$177
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 4/24
7:45 pm-8:45 pm
Nonstop2h 00m
Chicago Midway
Sun 4/26
7:40 am-10:30 am
Nonstop1h 50m
$177
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 4/15
6:40 pm-7:40 pm
Nonstop2h 00m
Chicago Midway
Fri 4/17
6:55 pm-9:45 pm
Nonstop1h 50m
$177
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Fri 5/1
5:21 pm-6:55 pm
Nonstop2h 34m
Chicago O'Hare Intl
Tue 5/5
11:00 am-2:09 pm
Nonstop2h 09m
$188
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Sat 5/16
5:51 pm-9:15 am
1 stop16h 24m
Chicago O'Hare Intl
Tue 5/19
5:34 pm-9:59 am
2 stops15h 25m
$195
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Wed 3/11
8:22 am-9:50 am
Nonstop2h 28m
Chicago O'Hare Intl
Wed 3/18
2:15 pm-5:17 pm
Nonstop2h 02m
$199
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 3/17
5:15 pm-6:51 pm
Nonstop2h 36m
Chicago O'Hare Intl
Wed 3/18
8:50 am-2:04 pm
1 stop4h 14m
$205
Showing 1-10 of 56 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-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
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 6, 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 $194). 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 12, 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 7, 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.
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 12, 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.
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
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 12, 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 12, 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 12, 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$150 | Average$318 | 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$311 | FlexibilityNo cancel fee | On-time63% |