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Midway

$83+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — MDW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Raleigh-Durham to Chicago Midway are usually found in September or February, booked 87 days in advance, depart on a Friday or Wednesday and return on a Wednesday

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 August 20, 2025.

Round-trip from

$139
(Southwest)

One-way from

$83
(CheapOair)

Popular in

May

Cheapest in

September

Average price

$248

Good round-trip deal

$193 or less

Good one-way deal

$118 or less
From Raleigh-Durham to Chicago Midway
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One-way flight from Raleigh-Durham to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Raleigh-Durham to Chicago Midway.
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Price to beat on a one-way flight from Raleigh-Durham to Chicago Midway.
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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 August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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 10/146:30 pmRDU - MDW
Nonstop2h 00mSouthwest
Sat 10/185:45 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 8/19$139
This CheapOair deal was found by Cheapflights users on 8/18. 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.
Sun 9/76:38 pmRDU - MDW
1 stop5h 42mFrontier
Tue 9/92:32 pmMDW - RDU
1 stop5h 05mFrontier
Deal found 8/18$143
This CheapOair deal was found by Cheapflights users on 8/19. 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 11/67:58 amRDU - MDW
1 stop7h 35mFrontier
Mon 11/109:15 amMDW - RDU
1 stop5h 47mFrontier
Deal found 8/19$144
This Priceline deal was found by Cheapflights users on 8/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:31 amRDU - MDW
1 stop7h 02mFrontier
Mon 11/39:15 amMDW - RDU
1 stop5h 47mFrontier
Deal found 8/19$145
This CheapOair deal was found by Cheapflights users on 8/19. 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 10/26:38 pmRDU - MDW
1 stop5h 42mFrontier
Sun 10/56:21 amMDW - RDU
1 stop9h 50mFrontier
Deal found 8/19$148
This CheapOair deal was found by Cheapflights users on 8/19. 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 9/116:38 pmRDU - MDW
1 stop5h 42mFrontier
Sun 9/1410:13 amMDW - RDU
1 stop22h 40mFrontier
Deal found 8/19$149
This CheapOair deal was found by Cheapflights users on 8/19. 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 11/67:58 amRDU - MDW
1 stop7h 35mFrontier
Sun 11/96:30 amMDW - RDU
1 stop13h 41mFrontier
Deal found 8/19$150
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:42 pmRDU - MDW
1 stop5h 38mFrontier
Mon 9/228:15 amMDW - RDU
1 stop4h 23mFrontier
Deal found 8/20$151
This CheapOair deal was found by Cheapflights users on 8/18. 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.
Fri 10/36:22 amRDU - MDW
1 stop10h 38mFrontier
Mon 10/68:15 amMDW - RDU
1 stop4h 23mFrontier
Deal found 8/18$152
This CheapOair deal was found by Cheapflights users on 8/19. 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.
Sat 9/206:06 pmRDU - MDW
1 stop19h 38mFrontier
Mon 9/226:21 amMDW - RDU
1 stop9h 50mFrontier
Deal found 8/19$153
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Fri 10/106:42 pmRDU - MDW
1 stop22h 27mFrontier
Sun 10/125:20 amMDW - RDU
1 stop9h 18mFrontier
Deal found 8/17$154
This CheapOair deal was found by Cheapflights users on 8/19. 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.
Wed 10/156:30 amRDU - MDW
1 stop28h 17mFrontier
Sun 10/1910:30 amMDW - RDU
1 stop9h 19mFrontier
Deal found 8/19$155

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 August 20, 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

Sat 11/1

6:35 am-7:30 am

Nonstop1h 55m

Chicago Midway

Tue 11/11

6:05 pm-8:55 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/25

6:35 am-7:30 am

Nonstop1h 55m

Chicago Midway

Sat 10/25

5:45 pm-8:35 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 9/17

6:40 am-7:35 am

Nonstop1h 55m

Chicago Midway

Wed 9/24

3:00 pm-5:50 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 10/14

6:30 pm-7:30 pm

Nonstop2h 00m

Chicago Midway

Sat 10/18

5:45 pm-8:35 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

4:55 pm-5:50 pm

Nonstop1h 55m

Chicago Midway

Sat 10/18

5:45 pm-8:35 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 10/1

6:00 pm-7:00 pm

Nonstop2h 00m

Chicago Midway

Sat 10/4

9:55 am-12:45 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 9/24

6:00 pm-7:00 pm

Nonstop2h 00m

Chicago Midway

Sat 9/27

9:50 am-12:45 pm

Nonstop1h 55m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 10/21

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sat 10/25

9:55 am-12:45 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 9/30

6:45 am-3:58 pm

1 stop10h 13m

Chicago Midway

Thu 10/2

4:56 pm-10:50 pm

1 stop4h 54m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 9/25

6:22 am-3:58 pm

1 stop10h 36m

Chicago Midway

Mon 9/29

5:15 pm-10:58 pm

1 stop4h 43m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 21 results
1
2
3

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

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 August 8, 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, April is the cheapest month in which you can book a flight from Raleigh to Chicago Midway Airport (average of $160). Flying from Raleigh to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 20, 2025.

It’s optimal to fly from Raleigh to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 11% 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 August 17, 2025.

Travelers seeking maximum savings on their Raleigh to Chicago Midway Airport flight should consider departing on Friday 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 August 20, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines 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
4,246 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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. 4 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 55m. The distance between Raleigh and Chicago Midway Airport is about 631 mi. All flights are typically nonstop.

  • 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 $106. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $157 and $178, respectively. Users have found that Frontier is 63% 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 $234, our data shows the cheapest flight currently is $88. 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, April is the cheapest month in which you can book a flight from Raleigh to Chicago Midway Airport (average of $160). Flying from Raleigh to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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Alternative routes for Raleigh to Midway

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Top 4 airlines flying from Raleigh to Midway

Discover the top 4 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$198FlexibilityNo cancel feeOn-time62%
DeltaCheapest$157Average$317FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$178Average$314FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$197Average$385FlexibilityNo cancel feeOn-time69%

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