RDU - MDW

$101 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 7/21. 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, 0 bags

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 24% 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.

Everything you should know

Cheapest round-trip
$201
Typical prices: $407-$287
Frontier
Sat 5/16Tue 5/19
RDU - MDW • 1 stop
Cheapest non-stop
$237
Typical prices: $339-$248
Southwest
Tue 6/2Wed 6/3
RDU - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest offers two free checked bags for extra luggage.
RDU provides free Wi-Fi for 48 hours per session.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $201 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 59m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $162 (round-trip)
Shortest trip • 4h 00m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 39% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight 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

Sat, May 16 - Tue, May 19
Frontier Logo
12:23 pm - 10:02 pm
RDU
-
MDW
10h 39m
1 stop
Frontier Logo
6:00 am - 12:04 pm
MDW
-
RDU
5h 04m
1 stop
$201Frontier
Wed, Jun 3 - Tue, Jun 9
Multiple Airlines Logo
10:03 pm - 10:02 pm
RDU
-
MDW
24h 59m
2 stops
Multiple Airlines Logo
6:00 am - 12:29 am
MDW
-
RDU
17h 29m
1 stop
$203Multiple Airlines
Tue, Jul 14 - Sat, Jul 18
Frontier Logo
6:15 am - 11:07 am
RDU
-
MDW
5h 52m
1 stop
Frontier Logo
12:11 pm - 12:25 am
MDW
-
RDU
11h 14m
1 stop
$204Frontier
Sat, Jun 6 - Sun, Jun 14
Frontier Logo
11:56 am - 10:02 pm
RDU
-
MDW
11h 06m
1 stop
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
$205Frontier
Sat, May 16 - Tue, May 19
Frontier Logo
12:23 pm - 10:02 pm
RDU
-
MDW
10h 39m
1 stop
Frontier Logo
6:00 am - 12:04 pm
MDW
-
RDU
5h 04m
1 stop
$206Frontier
Thu, May 14 - Sun, May 17
Frontier Logo
6:15 am - 11:09 am
RDU
-
MDW
5h 54m
1 stop
Frontier Logo
12:19 pm - 12:24 am
MDW
-
RDU
11h 05m
1 stop
$207Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
12:54 pm - 10:02 pm
RDU
-
MDW
10h 08m
1 stop
Frontier Logo
6:00 am - 7:08 pm
MDW
-
RDU
12h 08m
2 stops
$208Frontier
Wed, Jun 10 - Wed, Jun 17
Frontier Logo
6:15 am - 11:09 am
RDU
-
MDW
5h 54m
1 stop
Frontier Logo
12:04 pm - 12:21 am
MDW
-
RDU
11h 17m
1 stop
$209Frontier
Wed, Jun 24 - Sat, Jun 27
Frontier Logo
6:15 am - 11:09 am
RDU
-
MDW
5h 54m
1 stop
Frontier Logo
4:10 pm - 11:50 pm
MDW
-
RDU
6h 40m
1 stop
$210Frontier
Sat, May 23 - Tue, May 26
Frontier Logo
11:56 am - 10:02 pm
RDU
-
MDW
11h 06m
1 stop
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
$211Frontier
Booking Insights

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.

How much is a round-trip flight from Raleigh to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Raleigh to Chicago Midway Airport departing in May.

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 Wednesday, 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 Friday 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 October, where tickets cost $235 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $785 and $437 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 $297, 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 4 weeks before departure, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Raleigh to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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.

Jessica Macdonald

Jessica Macdonald

Expert on RDU

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.

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 26% 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 $101 for a one-way ticket and $201 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Raleigh to Chicago are Southwest and Frontier. With an average price for the route of $311 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $210 and an overall rating of 5.6.

  • 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 $179 or less one-way and $339 or less round-trip.

Prefer to fly direct from Raleigh to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Raleigh-Durham to Chicago Midway.
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

Reviews of the top airlines flying 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.
7.9
SouthwestOverall score based on 4310 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

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

Information on your arrival and departure airports