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Midway

$119+ Cheap flights from Raleigh (RDU) 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Cheapflights Tip: The best prices from Raleigh-Durham to Chicago Midway are usually found in October or January, booked 55 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap flight deals from Raleigh to Midway

Cheapest flights from Raleigh to Midway
Explore the most affordable flight options available from Raleigh to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2026.

This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:50 pm
RDU
-
MDW
2 stops7h 30m
Southwest
Sat 8/227:40 am
MDW
-
RDU
2 stops12h 05m
Southwest
Deal found 7/28$243
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 9/91:56 pm
RDU
-
MDW
1 stop4h 55m
Frontier
Mon 9/286:25 am
MDW
-
RDU
1 stop5h 13m
Frontier
Deal found 7/29$245
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 am
RDU
-
MDW
1 stop5h 50m
Southwest
Mon 8/3112:20 pm
MDW
-
RDU
2 stops8h 30m
Southwest
Deal found 7/28$246
This Frontier deal was found by Cheapflights users on 7/29. 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 9/101:56 pm
RDU
-
MDW
1 stop4h 50m
Frontier
Sat 9/266:25 am
MDW
-
RDU
1 stop5h 13m
Frontier
Deal found 7/29$248
This Booking.com deal was found by Cheapflights users on 7/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:56 pm
RDU
-
MDW
1 stop4h 55m
Frontier
Fri 9/186:46 pm
MDW
-
RDU
1 stop4h 43m
Frontier
Deal found 7/27$249
This Frontier deal was found by Cheapflights users on 7/29. 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 8/214:02 pm
RDU
-
MDW
1 stop7h 45m
Frontier
Mon 8/2411:50 am
MDW
-
RDU
1 stop11h 09m
Frontier
Deal found 7/29$250
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:30 pm
RDU
-
MDW
1 stop6h 45m
Southwest
Sun 9/69:30 am
MDW
-
RDU
2 stops11h 05m
Southwest
Deal found 7/28$251
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:40 am
RDU
-
MDW
2 stops7h 25m
Southwest
Mon 8/1710:30 am
MDW
-
RDU
1 stop7h 20m
Southwest
Deal found 7/25$252
This Frontier deal was found by Cheapflights users on 7/24. 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 8/1512:04 pm
RDU
-
MDW
1 stop10h 59m
Frontier
Mon 8/1711:06 am
MDW
-
RDU
1 stop10h 29m
Frontier
Deal found 7/24$253
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:45 pm
RDU
-
MDW
Nonstop1h 55m
Southwest
Fri 9/186:30 pm
MDW
-
RDU
Nonstop2h 00m
Southwest
Deal found 7/28$254
This Trip.com deal was found by Cheapflights users on 7/24. 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 9/241:56 pm
RDU
-
MDW
1 stop4h 50m
Frontier
Tue 9/296:25 am
MDW
-
RDU
1 stop5h 13m
Frontier
Deal found 7/24$256
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Thu 10/84:05 pm
RDU
-
MDW
1 stop6h 53m
Frontier
Mon 10/126:40 am
MDW
-
RDU
1 stop16h 37m
Frontier
Deal found 7/28$258

Find flight deals from Raleigh to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Raleigh (RDU) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$243
(Southwest)

One-way from

$119
(Southwest)

Popular in

February

Cheapest in

October

Average price

$350

Good round-trip deal

$349 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for Raleigh-Durham-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Raleigh-Durham-Chicago Midway flights.
Search Deals
From Raleigh-Durham to Chicago Midway
Search Deals
One-way flight from Raleigh-Durham to Chicago Midway
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Raleigh-Durham to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Raleigh-Durham to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Raleigh 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 July 29, 2026.
Use the filters below to find and compare flights from Raleigh 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

Wed 9/30

1:25 pm-2:15 pm

Nonstop1h 50m

Chicago Midway

Fri 10/2

5:50 pm-11:25 pm

1 stop4h 35m

$249

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 9/11

6:45 pm-7:40 pm

Nonstop1h 55m

Chicago Midway

Fri 9/18

3:15 pm-9:55 pm

1 stop5h 40m

$264

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/1

6:20 am-9:49 am

1 stop4h 29m

Chicago Midway

Sat 10/3

6:05 am-7:17 pm

2 stops12h 12m

$267

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/11

1:55 pm-8:05 pm

2 stops7h 10m

Chicago Midway

Mon 12/14

9:55 am-5:40 pm

1 stop6h 45m

$274

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 9/13

6:50 pm-7:45 pm

Nonstop1h 55m

Chicago Midway

Tue 9/15

8:35 am-11:35 am

Nonstop2h 00m

$277
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 8/27

8:25 am-9:15 am

Nonstop1h 50m

Chicago Midway

Sun 8/30

8:05 am-11:05 am

Nonstop2h 00m

$277

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 9/4

6:45 pm-7:40 pm

Nonstop1h 55m

Chicago Midway

Tue 9/8

8:35 am-11:35 am

Nonstop2h 00m

$277

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 9/7

2:40 pm-7:35 pm

2 stops5h 55m

Chicago Midway

Sat 9/12

7:55 am-4:35 pm

2 stops7h 40m

$279

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/8

6:55 am-7:55 am

Nonstop2h 00m

Chicago Midway

Sun 10/11

8:15 am-1:05 pm

1 stop3h 50m

$287

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 8/27

5:32 am-9:17 am

1 stop4h 45m

Chicago Midway

Wed 9/2

10:54 am-5:09 pm

1 stop5h 15m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Raleigh to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Raleigh to Midway in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Raleigh-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Raleigh-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Raleigh-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Raleigh-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Raleigh-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Raleigh to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Raleigh 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 Raleigh to Chicago Midway Airport

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

Booking 54 days in advance of your planned departure date is, on average, the best time to get cheap flights from Raleigh to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, October is the cheapest month in which you can book a flight from Raleigh to Chicago Midway Airport (average of $237). Flying from Raleigh to Chicago Midway Airport in February is currently the most expensive (average of $885). 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 RDU to MDW?

Find hourly flight availability from Raleigh 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 July 29, 2026.

It’s optimal to fly from Raleigh to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 16% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Raleigh to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Raleigh to Midway. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Raleigh 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.

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

Airfare is below average for this route at the moment.

Raleigh to Chicago Midway Airport flights typically cost between $297 and $391 in August.
The cheapest round-trip price found within the last 5 days was $243 on Southwest (Aug 20-Aug 22).

The best insider tips for Raleigh to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Raleigh to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on RDU

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

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 July 29, 2026.
Get a feel of what it's like to fly with Southwest,JetBlue, andFrontier from Raleigh to Chicago Midway Airport by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,024 reviews
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,749 reviews
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Raleigh to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Raleigh to Chicago Midway?

    For a flight from Raleigh to Chicago Midway, you will be flying from Raleigh-Durham. Raleigh-Durham (RDU) is just 11.1 mi from the center of the city. Raleigh-Durham is the only Raleigh airport and it handles 2 outbound flights to Chicago Midway per day. 3 airlines have flights to Chicago Midway from Raleigh-Durham on a regular basis.

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

    Departing from Raleigh to Chicago Midway Airport will take you 1h 50m. The distance between Raleigh and Chicago Midway Airport is about 631 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Raleigh to Chicago Midway Airport round-trip?

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $131. Additional round-trip tickets that might be worth considering are offered by Southwest and JetBlue, with the lowest prices starting at $188 and $224, respectively. Users have found that Frontier is 65% cheaper than the other options available to this destination.

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

    While on average a flight from Raleigh to Chicago Midway Airport is generally $342, our data shows the cheapest flight currently is $118. When looking at the most popular route, (Raleigh-Durham - Chicago Midway), you can expect to pay $187 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Raleigh 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 Raleigh to Chicago Midway Airport?

    Currently, October is the cheapest month in which you can book a flight from Raleigh to Chicago Midway Airport (average of $237). Flying from Raleigh to Chicago Midway Airport in February is currently the most expensive (average of $885). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 3 airlines flying from Raleigh to Midway

Discover the top 3 airlines that operate flights from Raleigh 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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$131Average$213FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$188Average$339FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$224Average$362FlexibilityNo cancel feeOn-time62%

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