RDU - MDW

$81 Find Cheap Flights from Raleigh to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Raleigh to Midway departing on 7/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Raleigh to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Raleigh to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flights from Raleigh to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Raleigh to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Raleigh to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Raleigh to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
7:40 pm - 8:40 pmRDU-MDW
2h 00mnonstop
Southwest Logo
7:45 pm - 10:35 pmMDW-RDU
1h 50mnonstop
$169Southwest
Find Deal
Wed, Jun 11 - Sat, Jun 14
Southwest Logo
6:15 am - 7:20 amRDU-MDW
2h 05mnonstop
Southwest Logo
6:30 pm - 9:20 pmMDW-RDU
1h 50mnonstop
$189Southwest
Find Deal
Wed, May 28 - Wed, May 28
Southwest Logo
2:25 pm - 3:20 pmRDU-MDW
1h 55mnonstop
Southwest Logo
6:05 pm - 9:05 pmMDW-RDU
2h 00mnonstop
$193Southwest
Find Deal
Wed, Jul 30 - Wed, Aug 6
Southwest Logo
3:40 pm - 4:35 pmRDU-MDW
1h 55mnonstop
Southwest Logo
9:00 am - 11:55 amMDW-RDU
1h 55mnonstop
$194Southwest
Find Deal
Sat, May 31 - Tue, Jun 3
Delta Logo
5:20 am - 9:41 amRDU-MDW
5h 21m1 stop
Delta Logo
1:09 pm - 5:38 pmMDW-RDU
3h 29m1 stop
$197Delta
Find Deal
Sat, Jun 14 - Tue, Jun 24
Frontier Logo
5:42 pm - 10:02 pmRDU-MDW
5h 20m1 stop
Frontier Logo
6:40 am - 6:59 pmMDW-RDU
11h 19m1 stop
$198Frontier
Find Deal
Sat, May 24 - Wed, May 28
Delta Logo
12:25 pm - 3:20 pmRDU-MDW
3h 55m1 stop
Delta Logo
1:08 pm - 5:32 pmMDW-RDU
3h 24m1 stop
$203Delta
Find Deal
Wed, May 28 - Sat, May 31
Frontier Logo
5:42 pm - 10:02 pmRDU-MDW
5h 20m1 stop
Frontier Logo
9:50 am - 4:04 pmMDW-RDU
5h 14m1 stop
$208Frontier
Find Deal
Sat, May 24 - Thu, May 29
Delta Logo
5:55 am - 8:40 amRDU-MDW
3h 45m1 stop
Delta Logo
12:48 pm - 5:52 pmMDW-RDU
4h 04m1 stop
$209Delta
Find Deal
Tue, May 27 - Wed, May 28
Frontier Logo
4:54 pm - 10:44 pmRDU-MDW
6h 50m1 stop
Frontier Logo
6:30 am - 4:24 pmMDW-RDU
8h 54m1 stop
$210Frontier
Find Deal
Tue, Jun 3 - Thu, Jun 5
Expert advice

Expert advice for your flight from Raleigh to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Southwest

Enjoy two free checked bags up to 50 pounds each, ideal for travelers with extra luggage.


Set an alarm to check in 24 hours before for a better boarding position.

Read more about Southwestby Blane Bachelor
Frontier

Choose the Economy Bundle for a carry-on and seat selection without change fees.


Pay for bags early online to save money compared to airport prices.

Read more about Frontierby Stefanie Waldek
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Useful Info

KAYAK's insights & trends for Raleigh to Midway flights

Get data-powered insights and trends into flights from Raleigh to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Raleigh to Chicago Midway Airport?

The average price of all round-trip flights from Raleigh to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Raleigh to Chicago Midway Airport. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Raleigh to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Raleigh to Chicago Midway Airport is June, where tickets cost $158 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $340 and $334 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Raleigh to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Raleigh to Chicago Midway Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonJanuary
High seasonJune
Cheapest flight$81
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly and prices are also 41% lower on average.
Flight from Raleigh to Chicago Midway Airport

When to book flights from Raleigh to Midway

Are your dates flexible? Find out the best times to travel from Raleigh to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Raleigh to Chicago Midway Airport flights

  • What is the cheapest flight from Raleigh to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Raleigh to Chicago Midway Airport was $81 for a one-way ticket and $169 for a round-trip.

  • Do I need a passport to fly between Raleigh and Chicago Midway Airport?

    No, a passport isn't needed to fly from Raleigh to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Raleigh to Chicago Midway Airport?

    Raleigh and Chicago Midway Airport are both served by 1 main airport. You will leave Raleigh from Raleigh-Durham and will be arriving at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Raleigh to Chicago Midway Airport?

    American Airlines, Delta, Alaska Airlines, and JetBlue offer inflight Wi-Fi service on the Raleigh to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Raleigh to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Raleigh to Chicago Midway Airport flight route.

  • On which days can I fly direct from Raleigh to Chicago Midway Airport?

    There are nonstop flights from Raleigh to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Raleigh to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Raleigh to Chicago are Southwest and Delta. With an average price for the route of $331 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $359 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Raleigh to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Raleigh to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Raleigh to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Raleigh is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Raleigh to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Raleigh with another airline. Booking your flights between Raleigh and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Raleigh to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Raleigh up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Raleigh to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $165 or less one-way and $273 or less round-trip.

Prefer to fly direct from Raleigh to Chicago Midway Airport?

Find which airlines fly direct from Raleigh-Durham Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Raleigh-Durham to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Raleigh-Durham

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 4 airlines serving from Raleigh to Midway

 
See real verified KAYAK customer reviews for airlines flying from Raleigh to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Raleigh to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

Food is terrible. Flight is outdated and seats are not comfy.

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

Good flight. On time. Boarding and seating was easy. Crew were really friendly, yet professional. Bathroom (by cockpit) was small but serviceable. Some the seats were showing some notable wear & tear, but were comfy. Very happy UA customer. TY! 🤛🏽💗

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight from Raleigh to Midway

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.