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Midway

$60+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
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 62 days in advance, depart on a Thursday or Wednesday 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 February 26, 2026.

This Southwest deal was found by Cheapflights users on 2/25. 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.
Fri 5/17:45 pm
RDU
-
MDW
Nonstop2h 00m
Southwest
Mon 5/46:55 pm
MDW
-
RDU
Nonstop1h 50m
Southwest
Deal found 2/25$163
This Trip.com deal was found by Cheapflights users on 2/25. 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.
Wed 3/184:12 pm
RDU
-
MDW
1 stop7h 07m
Frontier
Tue 3/246:00 am
MDW
-
RDU
1 stop8h 17m
Frontier
Deal found 2/25$168
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Thu 4/163:42 pm
RDU
-
MDW
1 stop7h 37m
Multiple Airlines
Mon 4/202:15 pm
MDW
-
RDU
2 stops17h 45m
Multiple Airlines
Deal found 2/25$169
This Trip.com deal was found by Cheapflights users on 2/24. 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 4/233:42 pm
RDU
-
MDW
1 stop4h 49m
Frontier
Sat 4/259:14 am
MDW
-
RDU
1 stop23h 45m
Frontier
Deal found 2/24$170
This CheapOair deal was found by Cheapflights users on 2/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:42 pm
RDU
-
MDW
1 stop4h 49m
Frontier
Sun 4/262:00 pm
MDW
-
RDU
1 stop16h 56m
Frontier
Deal found 2/23$171
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/244:12 pm
RDU
-
MDW
1 stop5h 42m
Frontier
Sun 3/296:00 am
MDW
-
RDU
1 stop17h 11m
Frontier
Deal found 2/22$172
This Southwest deal was found by Cheapflights users on 2/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:40 pm
RDU
-
MDW
Nonstop2h 00m
Southwest
Wed 4/296:05 pm
MDW
-
RDU
Nonstop1h 50m
Southwest
Deal found 2/24$173
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 4/86:00 am
RDU
-
MDW
1 stop15h 07m
Frontier
Sun 4/126:00 am
MDW
-
RDU
1 stop17h 15m
Frontier
Deal found 2/22$174
This Kiwi.com deal was found by Cheapflights users on 2/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:38 pm
RDU
-
MDW
1 stop26h 13m
Frontier
Mon 3/169:51 pm
MDW
-
RDU
1 stop23h 02m
Frontier
Deal found 2/23$175
This Southwest deal was found by Cheapflights users on 2/22. 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 4/86:40 pm
RDU
-
MDW
Nonstop2h 00m
Southwest
Wed 4/157:40 am
MDW
-
RDU
Nonstop1h 50m
Southwest
Deal found 2/22$177
This Kiwi.com deal was found by Cheapflights users on 2/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/164:07 pm
RDU
-
MDW
1 stop7h 12m
Frontier
Mon 3/239:51 pm
MDW
-
RDU
1 stop9h 46m
Frontier
Deal found 2/23$179
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/194:07 pm
RDU
-
MDW
1 stop7h 12m
Multiple Airlines
Thu 3/267:30 am
MDW
-
RDU
1 stop8h 59m
Multiple Airlines
Deal found 2/22$180

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 February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$163
(Southwest)

One-way from

$60
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$477

Good round-trip deal

$305 or less

Good one-way deal

$189 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. 10% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 26, 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

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 3/23

6:10 am-9:20 am

1 stop4h 10m

Chicago Midway

Mon 3/30

7:50 am-10:40 am

Nonstop1h 50m

$225

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 3/16

7:05 pm-8:10 pm

Nonstop2h 05m

Chicago Midway

Tue 3/17

3:35 pm-10:10 pm

1 stop5h 35m

$225

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 4/6

7:35 pm-11:00 pm

1 stop4h 25m

Chicago Midway

Wed 4/15

6:05 pm-8:55 pm

Nonstop1h 50m

$232

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 4/27

5:35 am-1:10 pm

2 stops8h 35m

Chicago Midway

Thu 4/30

11:45 am-6:30 pm

1 stop5h 45m

$250

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 4/22

1:25 pm-7:25 pm

2 stops7h 00m

Chicago Midway

Sat 4/25

10:30 am-6:55 pm

2 stops7h 25m

$261

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 4/10

7:45 pm-8:45 pm

Nonstop2h 00m

Chicago Midway

Sun 4/12

7:40 am-10:30 am

Nonstop1h 50m

$266

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 6/5

7:35 pm-8:35 pm

Nonstop2h 00m

Chicago Midway

Sun 6/7

7:40 am-10:35 am

Nonstop1h 55m

$297

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 4/7

8:10 am-9:10 am

Nonstop2h 00m

Chicago Midway

Tue 4/7

6:05 pm-8:55 pm

Nonstop1h 50m

$297

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/23

5:40 am-8:43 am

1 stop4h 03m

Chicago Midway

Sat 5/30

1:22 pm-5:52 pm

1 stop3h 30m

$317

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 7/24

3:30 pm-9:45 pm

1 stop7h 15m

Chicago Midway

Mon 7/27

5:59 pm-11:02 pm

1 stop4h 03m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/25

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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?

Use this chart to determine the optimal time to book a round-trip flight from Raleigh to Midway. Price data was last updated on February 20, 2026.

Booking 62 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, February is the cheapest month in which you can book a flight from Raleigh to Chicago Midway Airport (average of $93). Flying from Raleigh 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 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 February 26, 2026.

It’s optimal to fly from Raleigh to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 15% 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 February 21, 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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 26, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier 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
4,299 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
4,299 reviews
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
8,237 reviews
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
3,040 reviews
Southwest
8.0
Very good
4,299 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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 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 0 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 4h 10m. The distance between Raleigh and Chicago Midway Airport is about 631 mi.

  • 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 Delta and Southwest, with the lowest prices starting at $148 and $177, respectively. Users have found that Frontier is 58% 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 $299, our data shows the cheapest flight currently is $147. When looking at the most popular route, (Raleigh-Durham - Chicago Midway), you can expect to pay $159 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, February is the cheapest month in which you can book a flight from Raleigh to Chicago Midway Airport (average of $93). Flying from Raleigh 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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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 February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$131Average$208FlexibilityNo cancel feeOn-time62%
DeltaCheapest$148Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$311FlexibilityNo cancel feeOn-time63%

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