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Midway

$63+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Durham to Chicago Midway are usually found in October or February, booked 87 days in advance, depart on a Friday or Wednesday and return on a Wednesday

Cheap flight deals from Durham to Midway

Cheapest flights from Durham to Midway
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 December 12, 2025.

This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:05 pmRDU - MDW
1 stop10h 07mFrontier
Mon 1/56:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/11$163
This Southwest deal was found by Cheapflights users on 12/9. 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 12/255:30 amRDU - MDW
Nonstop2h 00mSouthwest
Thu 12/256:05 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 12/9$177
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:14 pmRDU - MDW
1 stop20h 51mFrontier
Thu 1/16:12 amMDW - RDU
1 stop4h 48mFrontier
Deal found 12/11$212
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1512:55 pmRDU - MDW
1 stop10h 17mFrontier
Wed 12/172:49 pmMDW - RDU
1 stop8h 23mFrontier
Deal found 12/10$213
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:05 pmRDU - MDW
1 stop10h 07mFrontier
Wed 12/313:10 pmMDW - RDU
1 stop16h 18mFrontier
Deal found 12/11$214
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:12 pmRDU - MDW
1 stop8h 46mFrontier
Sun 1/42:16 pmMDW - RDU
1 stop16h 57mFrontier
Deal found 12/10$217
This Southwest deal was found by Cheapflights users on 12/11. 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.
Wed 12/241:40 pmRDU - MDW
Nonstop2h 05mSouthwest
Wed 12/315:35 amMDW - RDU
1 stop5h 55mSouthwest
Deal found 12/11$222
This Frontier deal was found by Cheapflights users on 12/9. 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.
Mon 12/1512:55 pmRDU - MDW
1 stop10h 17mFrontier
Thu 12/186:12 amMDW - RDU
1 stop4h 48mFrontier
Deal found 12/9$238
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/291:15 pmRDU - MDW
1 stop9h 57mFrontier
Thu 1/16:12 amMDW - RDU
1 stop4h 48mFrontier
Deal found 12/10$239
This Frontier deal was found by Cheapflights users on 12/9. 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 12/1111:28 amRDU - MDW
1 stop11h 30mFrontier
Wed 12/172:49 pmMDW - RDU
1 stop8h 23mFrontier
Deal found 12/9$242

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 December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$128
(Frontier)

One-way from

$63
(Super.com)

Popular in

December

Cheapest in

October

Average price

$387
Provider with most accurate pricing for Raleigh-Durham-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Raleigh-Durham-Chicago (CHI) flights.
Search Deals
From Durham to Chicago Midway
Search Deals
One-way flight from Durham to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 2025.
Use the filters below to find and compare flights from Durham to Chicago Midway Airport that are best for you.

Fly from

Durham

Fly to

Midway

Route

Depart

Return

Price

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/25

8:15 am-11:25 am

1 stop4h 10m

Chicago Midway

Thu 12/25

6:05 pm-8:55 pm

Nonstop1h 50m

$187

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/14

5:15 am-10:27 am

1 stop6h 12m

Chicago Midway

Sun 1/18

6:45 am-11:52 am

1 stop4h 07m

$230

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/12

10:38 am-9:12 pm

1 stop11h 34m

Chicago Midway

Sun 2/15

6:00 am-3:45 pm

1 stop8h 45m

$233

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 1/10

5:35 pm-6:40 pm

Nonstop2h 05m

Chicago Midway

Sat 1/17

2:40 pm-7:20 pm

1 stop3h 40m

$239

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 2/14

5:30 am-8:53 am

1 stop4h 23m

Chicago Midway

Mon 2/16

6:17 pm-11:40 pm

1 stop4h 23m

$257

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/7

6:50 am-2:15 pm

2 stops8h 25m

Chicago Midway

Wed 1/14

1:25 pm-4:15 pm

Nonstop1h 50m

$258

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/15

12:45 pm-7:35 pm

2 stops7h 50m

Chicago Midway

Sun 1/18

10:15 am-5:20 pm

2 stops6h 05m

$259

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/7

5:15 am-10:27 am

1 stop6h 12m

Chicago Midway

Wed 1/7

5:31 pm-12:15 am

1 stop5h 44m

$263

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/14

6:15 am-1:10 pm

2 stops7h 55m

Chicago Midway

Wed 1/14

2:35 pm-8:40 pm

1 stop5h 05m

$268

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 1/12

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Wed 1/14

6:15 am-2:40 pm

1 stop7h 25m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
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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.
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

How far ahead should I book a flight from Durham to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Durham to Midway. Price data was last updated on December 5, 2025.

The price you pay for your flight from Durham to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 87 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Durham to Chicago Midway Airport?

Currently, February is the cheapest month in which you can book a flight from Durham to Chicago Midway Airport (average of $131). Flying from Durham to Chicago Midway Airport in March is currently the most expensive (average of $207). 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 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 December 12, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 30% on flights from Durham to Chicago Midway Airport by exploring options for tickets in the afternoon.

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 December 16, 2024.

Travelers seeking maximum savings on their Durham to Chicago Midway Airport flight should consider departing on Thursday afternoons 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 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 December 12, 2025.
Read through reviews of airlines operating flights from Durham to Chicago Midway Airport, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,253 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Durham to Chicago Midway Airport?

    Southwest, Delta, and Frontier can get you from Durham to Chicago Midway Airport in just under 4h 10m. Your travel time can differ by up to 7h 24m. The distance between Durham and Chicago Midway Airport is about 631 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Durham to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Raleigh-Durham - Chicago Midway) can be booked for $129 on average, our data indicates $309 when flying from Durham to Chicago Midway Airport.

  • Can I find deals for flights from Durham to Midway that include hotel bookings?

    Yes. In addition to deals on Durham to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Durham to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Durham to Midway.

  • Can I find deals for business class flights from Durham to Midway?

    Yes. Cheapflights offers flight deals from Durham to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Durham to Chicago Midway Airport?

    Currently, February is the cheapest month in which you can book a flight from Durham to Chicago Midway Airport (average of $131). Flying from Durham to Chicago Midway Airport in March is currently the most expensive (average of $207). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Durham to Midway

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Top 3 airlines flying from Durham to Midway

Discover the top 3 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$198FlexibilityNo cancel feeOn-time62%
DeltaCheapest$157Average$337FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$314FlexibilityNo cancel feeOn-time63%

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