$129+ Cheap flights from Durham, NC to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Durham to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Durham to Chicago are usually found in December or October, booked 81 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Durham to Chicago
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Best
Last-minute
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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 June 23, 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 June 23, 2026.
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:17 pm
RDU
- ORD
Nonstop2h 43m
American Airlines
Mon 8/108:40 pm
ORD
- RDU
Nonstop2h 02m
American Airlines
Deal found 6/21![American Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/83:50 pm
RDU
- MDW
Nonstop2h 00m
Southwest
Mon 8/108:50 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/22![Southwest logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:29 pm
RDU
- ORD
1 stop6h 41m
Frontier
Tue 7/141:50 pm
ORD
- RDU
1 stop17h 21m
Frontier
Deal found 6/18![Frontier logo]()
$254
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2012:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Wed 7/2212:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/21![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Fri 7/171:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/18![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:35 am
RDU
- MDW
1 stop5h 23m
Frontier
Sun 9/137:25 am
MDW
- RDU
1 stop15h 52m
Frontier
Deal found 6/23![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:56 am
RDU
- ORD
1 stop8h 57m
Frontier
Wed 7/151:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/18![Frontier logo]()
$256
This Trip.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Thu 8/611:06 am
MDW
- RDU
1 stop10h 38m
Frontier
Deal found 6/21![Frontier logo]()
$256
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:10 am
RDU
- ORD
1 stop4h 25m
Delta
Tue 7/145:18 pm
ORD
- RDU
1 stop5h 07m
Delta
Deal found 6/22![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:55 am
RDU
- MDW
1 stop3h 56m
Delta
Tue 8/116:42 pm
MDW
- RDU
1 stop3h 43m
Delta
Deal found 6/22![Delta logo]()
$257
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:30 pm
RDU
- ORD
1 stop13h 19m
Frontier
Tue 9/18:05 am
ORD
- RDU
1 stop12h 10m
Frontier
Deal found 6/21![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Thu 7/3012:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/23![Frontier logo]()
$258
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 June 23, 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 June 23, 2026.
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:10 am
RDU
- ORD
1 stop7h 41m
Delta
Tue 8/186:40 am
ORD
- RDU
1 stop6h 39m
Delta
Deal found 6/18![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:20 pm
RDU
- MDW
1 stop3h 55m
Southwest
Tue 7/2810:10 am
MDW
- RDU
2 stops6h 20m
Southwest
Deal found 6/19![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/310:59 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Thu 8/66:25 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 6/23![United Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:22 pm
RDU
- RFD
1 stop11h 51m
Multiple Airlines
Thu 7/3011:27 am
RFD
- RDU
2 stops19h 44m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:10 am
RDU
- ORD
1 stop4h 25m
Delta
Tue 7/216:22 pm
ORD
- RDU
1 stop4h 48m
Delta
Deal found 6/21![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:15 pm
RDU
- MDW
1 stop4h 45m
Southwest
Sat 7/2512:50 pm
MDW
- RDU
2 stops8h 10m
Southwest
Deal found 6/20![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
RDU
- MDW
2 stops6h 50m
Southwest
Sat 8/299:55 am
MDW
- RDU
2 stops9h 50m
Southwest
Deal found 6/21![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2011:29 am
RDU
- ORD
Nonstop2h 31m
United Airlines
Wed 9/236:28 pm
ORD
- RDU
Nonstop2h 21m
United Airlines
Deal found 6/19![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 6/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:40 pm
RDU
- MDW
1 stop4h 35m
Southwest
Tue 8/1812:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 6/18![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:15 am
RDU
- ORD
1 stop4h 58m
Delta
Wed 9/28:05 am
ORD
- RDU
1 stop5h 15m
Delta
Deal found 6/20![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:15 pm
RDU
- ORD
Nonstop2h 31m
United Airlines
Wed 9/1612:50 pm
ORD
- RDU
Nonstop2h 12m
United Airlines
Deal found 6/20![United Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/112:30 pm
RDU
- RFD
2 stops21h 07m
Multiple Airlines
Mon 7/137:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:45 pm
RDU
- MDW
2 stops6h 20m
Southwest
Wed 10/218:00 am
MDW
- RDU
2 stops7h 30m
Southwest
Deal found 6/22![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:51 pm
RDU
- ORD
1 stop6h 58m
Delta
Mon 8/246:40 am
ORD
- RDU
1 stop5h 05m
Delta
Deal found 6/20![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/810:59 am
RDU
- ORD
Nonstop2h 30m
United Airlines
Mon 8/106:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/22![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:30 am
RDU
- MDW
2 stops10h 30m
Southwest
Sun 9/69:30 am
MDW
- RDU
2 stops11h 05m
Southwest
Deal found 6/18![Southwest logo]()
$286
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/308:05 am
RDU
- ORD
Nonstop2h 26m
United Airlines
Sat 8/110:48 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/19![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:59 pm
RDU
- ORD
1 stop4h 54m
Delta
Tue 7/215:18 pm
ORD
- RDU
1 stop5h 07m
Delta
Deal found 6/21![Delta logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1610:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Mon 7/207:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:35 pm
RDU
- MDW
Nonstop2h 05m
Southwest
Mon 8/37:40 am
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 6/22![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Mon 7/275:12 pm
RDU
- ORD
Nonstop2h 30m
United Airlines
Sun 8/26:55 am
ORD
- RDU
Nonstop2h 13m
United Airlines
Deal found 6/18![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Thu 8/68:50 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 6/23![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1210:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Mon 7/137:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$493
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:15 am
RDU
- MDW
2 stops7h 45m
Southwest
Wed 7/291:15 pm
MDW
- RDU
2 stops7h 00m
Southwest
Deal found 6/23![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:29 pm
RDU
- RFD
1 stop13h 46m
Multiple Airlines
Mon 7/137:50 pm
RFD
- RDU
1 stop12h 35m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$502
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:05 pm
RDU
- MDW
1 stop6h 10m
Southwest
Sun 8/97:50 pm
MDW
- RDU
Nonstop1h 50m
Southwest
Deal found 6/20![Southwest logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:35 am
RDU
- RFD
2 stops13h 37m
Multiple Airlines
Mon 10/126:13 pm
RFD
- RDU
1 stop14h 46m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$668
Last-minute flights from Durham to ChicagoDiscover last-minute flight deals from Durham to Chicago. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Chicago. Data last updated June 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:56 am
RDU
- ORD
1 stop8h 57m
Frontier
Thu 7/161:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/18![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Fri 7/1712:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:56 am
RDU
- ORD
1 stop8h 57m
Frontier
Fri 7/171:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/18![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:15 am
RDU
- ORD
1 stop14h 38m
Frontier
Fri 7/171:50 pm
ORD
- RDU
1 stop9h 14m
Frontier
Deal found 6/18![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:15 am
RDU
- MDW
1 stop5h 52m
Frontier
Thu 7/1612:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$253
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:10 am
RDU
- ORD
1 stop4h 25m
Delta
Tue 7/145:18 pm
ORD
- RDU
1 stop5h 07m
Delta
Deal found 6/22![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:33 am
RDU
- MDW
1 stop4h 40m
Delta
Tue 7/216:00 am
MDW
- RDU
1 stop4h 35m
Delta
Deal found 6/22![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1511:56 am
RDU
- ORD
1 stop8h 57m
Multiple Airlines
Mon 7/208:05 am
ORD
- RDU
2 stops26h 10m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Sat 8/16:05 am
MDW
- RDU
1 stop16h 58m
Frontier
Deal found 6/18![Frontier logo]()
$255
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:56 am
RDU
- ORD
1 stop8h 57m
Frontier
Wed 7/229:57 pm
ORD
- RDU
1 stop12h 34m
Frontier
Deal found 6/21![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:15 am
RDU
- MDW
1 stop16h 48m
Frontier
Sun 7/266:05 am
MDW
- RDU
1 stop16h 59m
Frontier
Deal found 6/18![Frontier logo]()
$256
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Thu 7/3012:11 pm
MDW
- RDU
1 stop10h 53m
Frontier
Deal found 6/21![Frontier logo]()
$258
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 June 23, 2026.
Search for one-way flight options from Durham to Chicago. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:41 pm
RDU
- ORD
1 stop4h 30m
American Airlines
Deal found 6/21![American Airlines logo]()
$129
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:20 am
RDU
- MDW
1 stop5h 32m
Delta
Deal found 6/22![Delta logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/610:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$131
This Super.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:30 pm
RDU
- ORD
1 stop7h 17m
Frontier
Deal found 6/20![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:34 pm
RDU
- RFD
1 stop10h 15m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:59 pm
RDU
- MDW
2 stops24h 59m
Frontier
Deal found 6/20![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:04 pm
RDU
- ORD
1 stop8h 49m
Frontier
Deal found 6/19![Frontier logo]()
$133
This Trip.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/301:21 pm
RDU
- MDW
1 stop8h 11m
Frontier
Deal found 6/20![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:56 am
RDU
- RFD
2 stops23h 51m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 6/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:30 am
RDU
- MDW
2 stops10h 30m
Southwest
Deal found 6/18![Southwest logo]()
$134
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:09 pm
RDU
- ORD
Nonstop2h 30m
United Airlines
Deal found 6/20![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Deal found 6/21![Southwest logo]()
$135
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (American Airlines) |
One-way from | $129 (American Airlines) |
Popular in | February |
Cheapest in | December |
Average price | $337 |
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 June 23, 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 - ORD
RDUORD
Raleigh-Durham
Wed 8/12
10:10 am-4:51 pm
1 stop7h 41m
Chicago O'Hare Intl
Tue 8/18
6:40 am-2:19 pm
1 stop6h 39m
$257
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Tue 7/21
5:10 am-8:35 am
1 stop4h 25m
Chicago O'Hare Intl
Tue 7/21
6:22 pm-12:10 am
1 stop4h 48m
$257
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 7/22
8:20 pm-11:15 pm
1 stop3h 55m
Chicago Midway
Tue 7/28
10:10 am-5:30 pm
2 stops6h 20m
$262
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 7/18
6:15 pm-10:00 pm
1 stop4h 45m
Chicago Midway
Sat 7/25
12:50 pm-10:00 pm
2 stops8h 10m
$262
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 8/19
6:00 am-11:50 am
2 stops6h 50m
Chicago Midway
Sat 8/29
9:55 am-8:45 pm
2 stops9h 50m
$267
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 8/13
2:40 pm-6:15 pm
1 stop4h 35m
Chicago Midway
Tue 8/18
12:45 pm-6:50 pm
2 stops5h 05m
$274
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Tue 9/8
1:45 pm-7:05 pm
2 stops6h 20m
Chicago Midway
Wed 10/21
8:00 am-4:30 pm
2 stops7h 30m
$283
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/2
6:30 am-4:00 pm
2 stops10h 30m
Chicago Midway
Sun 9/6
9:30 am-9:35 pm
2 stops11h 05m
$286
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 8/1
6:35 pm-7:40 pm
Nonstop2h 05m
Chicago Midway
Mon 8/3
7:40 am-10:35 am
Nonstop1h 55m
$297
RaleighChicago
RDU - ORD
RDUORD
Raleigh-Durham
Mon 8/3
10:59 am-12:29 pm
Nonstop2h 30m
Chicago O'Hare Intl
Thu 8/6
6:25 pm-9:37 pm
Nonstop2h 12m
$303
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Durham to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Durham with our price prediction graph.
RDU-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 June 23, 2026.
One of the essential ways to save on airfare from Durham to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 24% on airfare.
Weekly flight availability from Durham to Chicago
Explore weekly flight availability from Durham to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 23, 2026.
The most flights from DU8 to CHI are scheduled on a Tuesday (39 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 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 June 20, 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 June 23, 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.
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Durham to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Durham to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 23, 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 June 23, 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$73 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$284 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$324 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$160 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$173 | Average$354 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$325 | FlexibilityNo cancel fee | On-time63% |