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Midway

$59+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Durham to Chicago Midway are usually found in October or February, booked 69 days in advance, depart on a Thursday 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/136:10 am
RDU
-
MDW
1 stop17h 15m
Frontier
Tue 2/176:00 am
MDW
-
RDU
1 stop17h 10m
Frontier
Deal found 1/28$144
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/186:25 am
RDU
-
MDW
1 stop13h 42m
Frontier
Thu 2/1912:22 pm
MDW
-
RDU
1 stop10h 48m
Frontier
Deal found 1/28$145
This Frontier deal was found by Cheapflights users on 1/28. 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
-
MDW
1 stop11h 06m
Frontier
Mon 3/22:19 pm
MDW
-
RDU
1 stop8h 51m
Frontier
Deal found 1/28$148
This Kiwi.com deal was found by Cheapflights users on 1/27. 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
Sun 3/19:04 pm
MDW
-
RDU
1 stop18h 11m
Frontier
Deal found 1/27$152
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/276:10 am
RDU
-
MDW
1 stop13h 28m
Frontier
Sun 3/19:04 pm
MDW
-
RDU
1 stop18h 11m
Frontier
Deal found 1/28$153
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/84:18 pm
RDU
-
MDW
1 stop7h 01m
Multiple Airlines
Thu 3/127:30 am
MDW
-
RDU
1 stop8h 59m
Multiple Airlines
Deal found 1/27$155
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/136:10 am
RDU
-
MDW
1 stop12h 43m
Frontier
Wed 2/187:00 am
MDW
-
RDU
1 stop11h 35m
Frontier
Deal found 1/27$156
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/96:08 pm
RDU
-
MDW
1 stop19h 54m
Multiple Airlines
Fri 3/132:41 pm
MDW
-
RDU
1 stop8h 30m
Multiple Airlines
Deal found 1/27$157
This Expedia deal was found by Cheapflights users on 1/26. 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 2/96:10 am
RDU
-
MDW
1 stop6h 35m
Frontier
Thu 2/126:25 am
MDW
-
RDU
1 stop10h 35m
Frontier
Deal found 1/26$160
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/47:10 am
RDU
-
MDW
1 stop5h 55m
Frontier
Fri 2/66:20 am
MDW
-
RDU
1 stop16h 51m
Frontier
Deal found 1/28$161
This Expedia deal was found by Cheapflights users on 1/28. 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 3/49:25 pm
RDU
-
MDW
1 stop18h 01m
Frontier
Mon 3/92:41 pm
MDW
-
RDU
1 stop8h 30m
Frontier
Deal found 1/28$163
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/176:20 am
RDU
-
MDW
1 stop13h 47m
Frontier
Wed 2/187:00 am
MDW
-
RDU
2 stops10h 52m
Frontier
Deal found 1/27$165

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$144
(Kiwi.com)

One-way from

$59
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$271
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. 5% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Tue 3/31

6:30 pm-7:35 pm

Nonstop2h 05m

Chicago Midway

Sat 4/4

6:45 pm-9:35 pm

Nonstop1h 50m

$231

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 3/4

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Mon 3/9

7:50 am-10:40 am

Nonstop1h 50m

$244

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 2/18

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Thu 2/19

10:45 am-4:00 pm

1 stop4h 15m

$255

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 2/23

6:20 pm-7:25 pm

Nonstop2h 05m

Chicago Midway

Thu 2/26

7:20 pm-10:10 pm

Nonstop1h 50m

$259

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/19

5:40 am-6:50 am

Nonstop2h 10m

Chicago Midway

Mon 2/23

6:05 pm-8:55 pm

Nonstop1h 50m

$259

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 2/25

3:15 pm-10:05 pm

2 stops7h 50m

Chicago Midway

Wed 3/4

10:05 am-5:20 pm

2 stops6h 15m

$261

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 4/7

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Thu 4/9

6:55 pm-9:45 pm

Nonstop1h 50m

$263

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 3/4

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Fri 3/6

6:45 pm-9:35 pm

Nonstop1h 50m

$263

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 4/16

7:45 pm-8:45 pm

Nonstop2h 00m

Chicago Midway

Mon 4/20

5:30 am-12:10 pm

1 stop5h 40m

$267

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 4/2

6:10 am-9:20 am

1 stop4h 10m

Chicago Midway

Mon 4/6

6:45 pm-9:35 pm

Nonstop1h 50m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 results
1
2

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 January 23, 2026.

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 69 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, October is the cheapest month in which you can book a flight from Durham to Chicago Midway Airport (average of $134). Flying from Durham to Chicago Midway Airport in December is currently the most expensive (average of $217). 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 January 29, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 12% 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 January 24, 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 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 January 29, 2026.
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
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

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
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

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
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

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 can get you from Durham to Chicago Midway Airport in just under 2h 05m. Your travel time will be generally consistent. The distance between Durham and Chicago Midway Airport is about 631 mi. Most flights are nonstop.

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

    Looking at all options, your cheapest flight can be booked for $123. While the most popular route (Raleigh-Durham - Chicago Midway) can be booked for $148 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, October is the cheapest month in which you can book a flight from Durham to Chicago Midway Airport (average of $134). Flying from Durham to Chicago Midway Airport in December is currently the most expensive (average of $217). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$131Average$222FlexibilityNo cancel feeOn-time62%
DeltaCheapest$148Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$314FlexibilityNo cancel feeOn-time63%

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