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Midway

$104+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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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 Friday

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 April 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:11 am
RDU
-
MDW
2 stops12h 51m
Multiple Airlines
Mon 5/1812:04 pm
MDW
-
RDU
1 stop11h 20m
Multiple Airlines
Deal found 4/26$194
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:52 pm
RDU
-
MDW
2 stops27h 10m
Frontier
Wed 5/2712:04 pm
MDW
-
RDU
1 stop11h 29m
Frontier
Deal found 4/26$195
This Trip.com deal was found by Cheapflights users on 4/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:15 pm
RDU
-
MDW
1 stop18h 42m
Frontier
Sun 5/176:00 am
MDW
-
RDU
1 stop5h 02m
Frontier
Deal found 4/23$196
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 6/86:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Fri 6/1912:04 pm
MDW
-
RDU
1 stop11h 17m
Frontier
Deal found 4/25$199
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/1310:16 am
RDU
-
MDW
2 stops12h 46m
Frontier
Tue 6/912:27 pm
MDW
-
RDU
1 stop11h 02m
Frontier
Deal found 4/25$200
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 am
RDU
-
MDW
1 stop5h 49m
Frontier
Mon 5/1112:04 pm
MDW
-
RDU
1 stop11h 20m
Frontier
Deal found 4/27$201
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Wed 5/273:07 pm
MDW
-
RDU
2 stops17h 14m
Frontier
Deal found 4/26$203
This Trip.com deal was found by Cheapflights users on 4/25. 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 5/76:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Tue 5/126:00 am
MDW
-
RDU
1 stop5h 04m
Frontier
Deal found 4/25$204
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Sun 5/246:00 am
MDW
-
RDU
1 stop4h 59m
Frontier
Deal found 4/26$205
This Frontier deal was found by Cheapflights users on 4/25. 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 5/206:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Sun 5/246:00 am
MDW
-
RDU
1 stop4h 59m
Frontier
Deal found 4/25$206
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 6/1712:10 pm
RDU
-
MDW
1 stop11h 01m
Frontier
Thu 8/612:11 pm
MDW
-
RDU
1 stop11h 14m
Frontier
Deal found 4/27$207

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$194
(Kiwi.com)

One-way from

$104
(Trip.com)

Popular in

February

Cheapest in

October

Average price

$330
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. 28% potential increase in price ($141 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 28, 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

Price

Cheapest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 7/12

6:15 am-11:07 am

1 stop5h 52m

Chicago Midway

Tue 7/14

6:00 am-11:54 am

1 stop4h 54m

$210

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 5/26

4:15 pm-9:09 pm

1 stop5h 54m

Chicago Midway

Wed 5/27

5:12 pm-12:16 am

1 stop6h 04m

$221

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 6/2

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Wed 6/10

5:30 pm-10:50 pm

1 stop4h 20m

$247
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 5/27

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Fri 5/29

6:55 pm-9:45 pm

Nonstop1h 50m

$247

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 5/24

5:40 am-8:43 am

1 stop4h 03m

Chicago Midway

Sun 5/24

6:36 pm-11:26 pm

1 stop3h 50m

$257

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 7/3

7:35 pm-8:35 pm

Nonstop2h 00m

Chicago Midway

Sun 7/5

7:40 am-10:35 am

Nonstop1h 55m

$287

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/10

7:00 pm-8:00 pm

Nonstop2h 00m

Chicago Midway

Sat 6/13

12:50 pm-3:45 pm

Nonstop1h 55m

$287

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 7/3

7:35 pm-8:35 pm

Nonstop2h 00m

Chicago Midway

Mon 7/6

7:40 am-10:35 am

Nonstop1h 55m

$297

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 6/13

6:15 pm-9:55 pm

1 stop4h 40m

Chicago Midway

Tue 6/16

11:25 am-2:15 pm

Nonstop1h 50m

$297

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 9/12

5:45 am-8:42 am

1 stop3h 57m

Chicago Midway

Tue 9/15

5:59 pm-11:02 pm

1 stop4h 03m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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

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 April 28, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 21% 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 April 25, 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.

How much does it cost to fly round-trip from Durham to Chicago Midway Airport?

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 April 28, 2026.
Read through reviews of airlines operating flights from Durham to Chicago Midway Airport, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,313 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,313 reviews
Southwest
8.0
Very good
4,313 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,464 reviews
Southwest
8.0
Very good
4,313 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,971 reviews
Southwest
8.0
Very good
4,313 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    Frontier, Delta, and Southwest can get you from Durham to Chicago Midway Airport in just under 2h. Your travel time can differ by up to 3h 54m. 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 $118. While the most popular route (Raleigh-Durham - Chicago Midway) can be booked for $153 on average, our data indicates $332 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$213FlexibilityNo cancel feeOn-time62%
DeltaCheapest$148Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$303FlexibilityNo cancel feeOn-time63%

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