RDU - MDW

$70 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 8/12. 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
1 adult, Economy

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
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Flights Deals

Cheap Flights from Raleigh to Midway (RDU-MDW)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Raleigh to Midway

Wed, Aug 6 - Wed, Aug 13
Southwest Logo
6:40 am - 7:35 amRDU-MDW
1h 55mnonstop
Southwest Logo
6:05 pm - 9:05 pmMDW-RDU
2h 00mnonstop
$139Southwest
Find Deal
Tue, Aug 5 - Sat, Aug 9
Southwest Logo
1:35 pm - 2:30 pmRDU-MDW
1h 55mnonstop
Southwest Logo
5:40 pm - 8:35 pmMDW-RDU
1h 55mnonstop
$148Southwest
Find Deal
Mon, Sep 15 - Thu, Sep 18
Southwest Logo
6:30 pm - 7:30 pmRDU-MDW
2h 00mnonstop
Southwest Logo
6:25 pm - 9:20 pmMDW-RDU
1h 55mnonstop
$157Southwest
Find Deal
Tue, Aug 5 - Sat, Aug 9
Southwest Logo
2:05 pm - 5:05 pmRDU-MDW
4h 00m1 stop
Southwest Logo
5:40 pm - 8:35 pmMDW-RDU
1h 55mnonstop
$158Southwest
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
12:20 pm - 7:39 amRDU-MDW
20h 19m1 stop
Frontier Logo
8:15 am - 1:38 pmMDW-RDU
4h 23m1 stop
$185Frontier
Find Deal
Wed, Aug 27 - Fri, Aug 29
Delta Logo
5:45 am - 8:35 amRDU-MDW
3h 50m1 stop
Delta Logo
6:17 pm - 11:16 pmMDW-RDU
3h 59m1 stop
$197Delta
Find Deal
Fri, Oct 24 - Mon, Oct 27
Frontier Logo
7:10 pm - 11:25 pmRDU-MDW
5h 15m1 stop
Frontier Logo
6:21 am - 5:00 pmMDW-RDU
9h 39m1 stop
$200Frontier
Find Deal
Sun, Aug 17 - Wed, Aug 27
Delta Logo
5:45 am - 8:35 amRDU-MDW
3h 50m1 stop
Delta Logo
6:00 am - 11:15 amMDW-RDU
4h 15m1 stop
$207Delta
Find Deal
Tue, Aug 5 - Fri, Aug 8
Delta Logo
1:00 pm - 6:40 pmRDU-MDW
6h 40m1 stop
Delta Logo
6:20 pm - 11:16 pmMDW-RDU
3h 56m1 stop
$208Delta
Find Deal
Fri, Oct 10 - Tue, Oct 14
Frontier Logo
7:10 pm - 11:25 pmRDU-MDW
5h 15m1 stop
Frontier Logo
8:00 am - 3:37 pmMDW-RDU
6h 37m1 stop
$250Frontier
Find Deal
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
Airports
RDU

RDU offers free Wi-Fi throughout the airport, lasting 48 hours per session, perfect for staying connected during any delays.

Read more about RDUby Jessica Macdonald
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes, avoiding traffic issues.

Read more about MDWby 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 and MDW

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
Jessica Macdonald

Jessica Macdonald

Expert on RDU

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

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 September, where tickets cost $224 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $366 and $340 respectively.

Can I save money by flying with a layover from Raleigh to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $243, prices are generally cheapest when you fly direct.

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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonApril
High seasonJune
Cheapest flight$70
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 11% 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 $70 for a one-way ticket and $139 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, JetBlue, and Alaska Airlines 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 $316 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 $350 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 $124 or less one-way and $229 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 4287 reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Turbulent taking off & landing to Dulles from Raleigh. Flight from Dulles to Tokyo very good!!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

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

Information on your arrival and departure airports

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