$118+ Cheap flights from Durham, NC to Midway (MDW)
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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from Durham to Midway 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 Midway are usually found in October or January, booked 55 days in advance, depart on a Wednesday or Thursday and return on a Wednesday
Cheap flight deals from Durham to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Durham to MidwayExplore the most affordable flight options available from Durham to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
Explore the most affordable flight options available from Durham to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:59 pm
RDU
- MDW
1 stop6h 01m
Delta
Tue 11/311:39 am
MDW
- RDU
1 stop4h 26m
Delta
Deal found 7/31![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 pm
RDU
- MDW
1 stop7h 45m
Southwest
Tue 9/812:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 8/3![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
RDU
- MDW
2 stops15h 26m
Frontier
Sat 8/2211:45 am
MDW
- RDU
1 stop11h 14m
Frontier
Deal found 7/30![Frontier logo]()
$244
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Thu 9/175:30 am
MDW
- RDU
1 stop8h 55m
Southwest
Deal found 8/3![Southwest logo]()
$245
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Thu 8/2711:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/31![Frontier logo]()
$246
This Expedia deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Sun 9/611:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 8/2![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:05 pm
RDU
- MDW
1 stop6h 53m
Frontier
Sun 10/1112:03 pm
MDW
- RDU
1 stop11h 14m
Frontier
Deal found 7/30![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:04 pm
RDU
- MDW
1 stop10h 59m
Frontier
Tue 8/2511:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/30![Frontier logo]()
$249
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:05 am
RDU
- MDW
2 stops7h 25m
Southwest
Mon 8/246:30 pm
MDW
- RDU
Nonstop1h 55m
Southwest
Deal found 8/2![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:15 am
RDU
- MDW
2 stops9h 05m
Southwest
Sat 9/59:20 am
MDW
- RDU
2 stops10h 40m
Southwest
Deal found 7/31![Southwest logo]()
$251
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Mon 8/2411:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 8/1![Frontier logo]()
$253
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Thu 9/311:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/30![Frontier logo]()
$254
Best flights from Durham to MidwayDiscover carefully curated flight deals from Durham to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from Durham to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:25 pm
RDU
- MDW
Nonstop1h 50m
Southwest
Thu 9/247:55 am
MDW
- RDU
1 stop4h 05m
Southwest
Deal found 8/3![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Mon 9/149:00 am
MDW
- RDU
1 stop4h 00m
Southwest
Deal found 8/3![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:55 pm
RDU
- MDW
1 stop4h 05m
Southwest
Sun 9/68:55 am
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 8/1![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:10 am
RDU
- MDW
1 stop3h 55m
Southwest
Sat 11/1410:20 am
MDW
- RDU
2 stops8h 00m
Southwest
Deal found 7/31![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:45 am
RDU
- MDW
1 stop9h 15m
Southwest
Sat 9/267:55 am
MDW
- RDU
2 stops7h 50m
Southwest
Deal found 8/2![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am
RDU
- MDW
2 stops6h 50m
Southwest
Tue 9/2212:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 8/1![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:45 pm
RDU
- MDW
2 stops6h 20m
Southwest
Wed 9/162:00 pm
MDW
- RDU
2 stops6h 25m
Southwest
Deal found 7/31![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:45 pm
RDU
- MDW
2 stops6h 20m
Southwest
Sat 9/127:40 am
MDW
- RDU
2 stops7h 55m
Southwest
Deal found 8/4![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:50 pm
RDU
- MDW
2 stops7h 35m
Southwest
Tue 9/1510:30 am
MDW
- RDU
2 stops7h 35m
Southwest
Deal found 8/1![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:55 pm
RDU
- MDW
1 stop4h 00m
Southwest
Fri 8/2810:05 am
MDW
- RDU
2 stops7h 15m
Southwest
Deal found 7/30![Southwest logo]()
$274
Last-minute flights from Durham to MidwayDiscover last-minute flight deals from Durham to Midway. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Durham to Midway. Data last updated August 4, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Thu 8/2711:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/31![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
RDU
- MDW
2 stops15h 26m
Frontier
Sat 8/2211:45 am
MDW
- RDU
1 stop11h 14m
Frontier
Deal found 7/30![Frontier logo]()
$244
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Mon 8/2411:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 8/1![Frontier logo]()
$253
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:15 am
RDU
- MDW
1 stop6h 36m
Delta
Sat 8/299:24 am
MDW
- RDU
1 stop6h 02m
Delta
Deal found 8/3![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Thu 9/36:30 pm
MDW
- RDU
Nonstop2h 00m
Southwest
Deal found 7/30![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:15 am
RDU
- MDW
2 stops9h 05m
Southwest
Sat 9/59:20 am
MDW
- RDU
2 stops10h 40m
Southwest
Deal found 7/31![Southwest logo]()
$251
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Thu 9/311:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 7/30![Frontier logo]()
$254
This Expedia deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am
RDU
- MDW
1 stop5h 50m
Frontier
Sun 9/611:50 am
MDW
- RDU
1 stop11h 09m
Frontier
Deal found 8/2![Frontier logo]()
$247
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 pm
RDU
- MDW
1 stop7h 45m
Southwest
Tue 9/812:45 pm
MDW
- RDU
2 stops5h 05m
Southwest
Deal found 7/31![Southwest logo]()
$242
This Booking.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:56 pm
RDU
- MDW
1 stop4h 50m
Frontier
Sun 9/206:46 pm
MDW
- RDU
1 stop4h 43m
Frontier
Deal found 7/30![Frontier logo]()
$248
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:45 pm
RDU
- MDW
Nonstop1h 55m
Southwest
Thu 9/175:30 am
MDW
- RDU
1 stop8h 55m
Southwest
Deal found 8/3![Southwest logo]()
$245
One-way flights from Durham to MidwaySearch for one-way flight options from Durham to Midway. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from Durham to Midway. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:10 am
RDU
- MDW
Nonstop2h 05m
Southwest
Deal found 7/31![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:15 am
RDU
- MDW
2 stops9h 05m
Southwest
Deal found 7/30![Southwest logo]()
$119
This Trip.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:15 am
RDU
- MDW
1 stop16h 48m
Frontier
Deal found 8/2![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:05 am
RDU
- MDW
2 stops15h 26m
Frontier
Deal found 7/30![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:56 pm
RDU
- MDW
1 stop4h 50m
Frontier
Deal found 7/30![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:04 pm
RDU
- MDW
2 stops28h 54m
Frontier
Deal found 7/31![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:56 pm
RDU
- MDW
1 stop4h 50m
Frontier
Deal found 7/30![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:35 am
RDU
- MDW
1 stop5h 23m
Frontier
Deal found 7/30![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:54 pm
RDU
- MDW
1 stop20h 04m
Frontier
Deal found 8/1![Frontier logo]()
$127
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:10 am
RDU
- MDW
1 stop5h 49m
Delta
Deal found 7/31![Delta logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:09 pm
RDU
- MDW
2 stops28h 44m
Frontier
Deal found 8/1![Frontier logo]()
$129
Find flight deals from Durham to Midway
Keep the following information in mind while searching for Durham to Midway flight deals. Data was last updated August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Delta) |
One-way from | $118 (Southwest) |
Popular in | February |
Cheapest in | October |
Average price | $347 |
Cheapflights Fare Finder
Customize your flight search to find flights from Durham to Midway 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 August 4, 2026.
Use the filters below to find and compare flights from Durham to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/16
1:25 pm-2:15 pm
Nonstop1h 50m
Chicago Midway
Thu 9/24
7:55 am-1:00 pm
1 stop4h 05m
$245
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 9/10
6:45 pm-7:40 pm
Nonstop1h 55m
Chicago Midway
Mon 9/14
9:00 am-2:00 pm
1 stop4h 00m
$245
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Fri 9/4
6:55 pm-10:00 pm
1 stop4h 05m
Chicago Midway
Sun 9/6
8:55 am-11:55 am
Nonstop2h 00m
$259
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Sat 11/14
6:10 am-9:05 am
1 stop3h 55m
Chicago Midway
Sat 11/14
10:20 am-7:20 pm
2 stops8h 00m
$260
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/23
7:45 am-4:00 pm
1 stop9h 15m
Chicago Midway
Sat 9/26
7:55 am-4:45 pm
2 stops7h 50m
$260
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Tue 9/15
6:00 am-11:50 am
2 stops6h 50m
Chicago Midway
Tue 9/22
12:45 pm-6:50 pm
2 stops5h 05m
$261
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/9
1:45 pm-7:05 pm
2 stops6h 20m
Chicago Midway
Wed 9/16
2:00 pm-9:25 pm
2 stops6h 25m
$265
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Wed 9/9
1:45 pm-7:05 pm
2 stops6h 20m
Chicago Midway
Sat 9/12
7:40 am-4:35 pm
2 stops7h 55m
$265
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Mon 9/14
4:50 pm-11:25 pm
2 stops7h 35m
Chicago Midway
Tue 9/15
10:30 am-7:05 pm
2 stops7h 35m
$265
RaleighChicago
RDU - MDW
RDUMDW
Raleigh-Durham
Thu 8/27
6:55 pm-9:55 pm
1 stop4h 00m
Chicago Midway
Fri 8/28
10:05 am-6:20 pm
2 stops7h 15m
$274
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Durham to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Durham with our price prediction graph.
RDU-MDW
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 Midway Airport
DU8-MDW
RDU-MDW
What is the cheapest time of day to fly from DU8 to MDW?
Find hourly flight availability from Durham to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 4, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 17% on flights from Durham to Chicago Midway Airport by exploring options for tickets in the afternoon.
How much does it cost to fly round-trip from Durham to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Durham to Chicago Midway Airport flights typically cost between $297 and $391 in October.The cheapest round-trip price found within the last 5 days was $241 on Delta (Oct 30-Nov 3).
What is the cheapest day to fly from Durham to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Durham to Midway. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Durham to Chicago Midway Airport flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated August 4, 2026.
Read through reviews of airlines operating flights from Durham to Chicago Midway Airport, such as Southwest,JetBlue, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
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 Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Durham to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Durham to Midway by cabin class
Find flights from Durham to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 4, 2026.
Durham and Midway flights
Browse other Durham and Midway flight options. Last updated on August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Durham to Midway flights
Consider these flights traveling from Durham to Midway.
Top 4 airlines flying from Durham to Midway
Discover the top 4 airlines that operate flights from Durham to Midway. 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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$222 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$188 | Average$342 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$224 | Average$362 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$249 | Average$313 | FlexibilityNo cancel fee | On-timeN/A |