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$61+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheapflights Tip: The best prices from Raleigh-Durham to Chicago Midway are usually found in February or October, booked 87 days in advance, depart on a Thursday or Friday and return on a Wednesday

Find 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 October 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/76:00 amRDU - MDW
1 stop13h 04mFrontier
Wed 12/102:49 pmMDW - RDU
1 stop8h 23mFrontier
Deal found 10/16$131
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/176:10 amRDU - MDW
1 stop13h 29mMultiple Airlines
Sun 11/236:20 amMDW - RDU
1 stop6h 15mMultiple Airlines
Deal found 10/16$135
This Southwest deal was found by Cheapflights users on 10/15. 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 12/65:10 pmRDU - MDW
Nonstop2h 05mSouthwest
Sat 12/139:50 amMDW - RDU
Nonstop1h 55mSouthwest
Deal found 10/15$139
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/126:10 amRDU - MDW
1 stop7h 31mFrontier
Sun 11/166:15 amMDW - RDU
1 stop10h 47mFrontier
Deal found 10/15$141
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/126:10 amRDU - MDW
1 stop7h 31mFrontier
Sat 11/151:37 pmMDW - RDU
1 stop8h 21mFrontier
Deal found 10/16$144
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/75:51 pmRDU - MDW
1 stop19h 46mFrontier
Tue 11/111:56 pmMDW - RDU
1 stop26h 12mFrontier
Deal found 10/15$145
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 10/296:10 amRDU - MDW
1 stop7h 31mFrontier
Fri 10/319:32 amMDW - RDU
1 stop7h 54mFrontier
Deal found 10/14$146
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/2112:55 pmRDU - MDW
1 stop25h 26mFrontier
Wed 12/248:15 amMDW - RDU
1 stop14h 58mFrontier
Deal found 10/16$147
This Southwest deal was found by Cheapflights users on 10/16. 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 11/121:40 pmRDU - MDW
Nonstop2h 05mSouthwest
Sat 11/159:50 amMDW - RDU
Nonstop1h 55mSouthwest
Deal found 10/16$149
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 12/511:13 amRDU - MDW
1 stop9h 29mFrontier
Sun 12/77:47 pmMDW - RDU
1 stop15h 11mFrontier
Deal found 10/15$150
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/296:10 amRDU - MDW
1 stop7h 31mFrontier
Sat 11/16:30 amMDW - RDU
2 stops15h 28mFrontier
Deal found 10/15$151
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/302:54 pmRDU - MDW
1 stop9h 31mFrontier
Fri 10/319:32 amMDW - RDU
1 stop7h 54mFrontier
Deal found 10/15$152

Cheap 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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$130
(Kiwi.com)

One-way from

$61
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$247

Good round-trip deal

$247 or less

Good one-way deal

$129 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. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 16, 2025.
Use the filters below to find and compare flights from Raleigh to Chicago Midway Airport that are best for you.

Fly from

Raleigh

Fly to

Midway

Route

Depart

Return

Price

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 12/7

6:00 am-6:04 pm

1 stop13h 04m

Chicago Midway

Wed 12/10

2:49 pm-12:12 am

1 stop8h 23m

$131

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 12/7

5:45 am-6:50 am

Nonstop2h 05m

Chicago Midway

Wed 12/10

1:45 pm-4:30 pm

Nonstop1h 45m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 11/5

6:10 am-12:41 pm

1 stop7h 31m

Chicago Midway

Fri 11/7

6:15 am-5:44 pm

1 stop10h 29m

$172

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 11/14

5:45 am-6:50 am

Nonstop2h 05m

Chicago Midway

Sun 11/16

9:45 am-12:40 pm

Nonstop1h 55m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 2/1

5:45 am-8:50 am

1 stop4h 05m

Chicago Midway

Tue 2/3

1:05 pm-7:53 pm

1 stop5h 48m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 2/3

5:45 am-8:50 am

1 stop4h 05m

Chicago Midway

Wed 2/4

5:25 pm-11:53 pm

1 stop5h 28m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 11/14

5:45 am-6:50 am

Nonstop2h 05m

Chicago Midway

Mon 11/17

10:00 am-1:00 pm

Nonstop2h 00m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/4

6:10 am-9:55 am

1 stop4h 45m

Chicago Midway

Sun 12/14

9:45 am-12:40 pm

Nonstop1h 55m

$198

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 12/10

6:30 pm-7:35 pm

Nonstop2h 05m

$70

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 1/20

4:55 pm-6:00 pm

Nonstop2h 05m

$70

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 20 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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?

Use this chart to determine the optimal time to book a round-trip flight from Raleigh to Midway. Price data was last updated on October 10, 2025.

Booking 87 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 $131). Flying from Raleigh to Chicago Midway Airport in December is currently the most expensive (average of $233). 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 October 16, 2025.

It’s optimal to fly from Raleigh to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 12% on the cost of your flight, compared to a flight at noon.

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 October 12, 2025.

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. Friday 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

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Raleigh to Chicago Midway Airport trip
Airports
RDU

RDU offers free Wi-Fi throughout the terminals. Connect to the 'RDU Free WiFi' network for seamless browsing before your flight.

Read more about RDUby John Walton
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable transit option.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

John Walton

John Walton

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 October 16, 2025.
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
4,241 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,137 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 1 outbound flight 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 2h 05m. 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 $108. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $157 and $177, respectively. Users have found that Frontier is 64% 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 $282, our data shows the cheapest flight currently is $89. When looking at the most popular route, (Raleigh-Durham - Chicago Midway), you can expect to pay $139 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 $131). Flying from Raleigh to Chicago Midway Airport in December is currently the most expensive (average of $233). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Raleigh to Midway

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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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$184FlexibilityNo cancel feeOn-time62%
DeltaCheapest$157Average$318FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$318FlexibilityNo cancel feeOn-time63%

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