$81 Cheap Flights from Raleigh (RDU) to Chicago (MDW)

View $81 flight on Sat, Jul 5, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Raleigh to Chicago (RDU-MDW)

Prices were available within the past 7 days and start at $81 for one-way flights and $161 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jul 1 - Thu, Jul 3
RDU
Raleigh
MDW
Chicago
$161 Roundtrip, found 3 hours ago
$161
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Raleigh to Chicago, returning Thu, Jul 3, priced at $161 found 3 hours ago
Southwest Airlines
Sat, Jun 21 - Thu, Jul 3
RDU
Raleigh
MDW
Chicago
$165 Roundtrip, found 7 hours ago
$165
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Jun 21 from Raleigh to Chicago, returning Thu, Jul 3, priced at $165 found 7 hours ago
Southwest Airlines
Wed, May 28 - Sat, Jun 7
RDU
Raleigh
MDW
Chicago
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, May 28 from Raleigh to Chicago, returning Sat, Jun 7, priced at $169 found 1 hour ago
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
RDU
Raleigh
MDW
Chicago
$171 Roundtrip, found 3 hours ago
$171
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Raleigh to Chicago, returning Sat, Jul 5, priced at $171 found 3 hours ago
Southwest Airlines
Tue, May 20 - Tue, May 27
RDU
Raleigh
MDW
Chicago
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, May 20 from Raleigh to Chicago, returning Tue, May 27, priced at $174 found 6 days ago
Southwest Airlines
Sat, Jun 21 - Thu, Jul 3
RDU
Raleigh
MDW
Chicago
$175 Roundtrip, found 7 hours ago
$175
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Jun 21 from Raleigh to Chicago, returning Thu, Jul 3, priced at $175 found 7 hours ago
Southwest Airlines
Wed, Jun 18 - Sat, Jun 21
RDU
Raleigh
MDW
Chicago
$178 Roundtrip, found 14 hours ago
$178
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Wed, Jun 18 from Raleigh to Chicago, returning Sat, Jun 21, priced at $178 found 14 hours ago
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
RDU
Raleigh
MDW
Chicago
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Raleigh to Chicago, returning Sat, Jul 5, priced at $179 found 3 hours ago
Delta
Sat, May 31 - Tue, Jun 10
RDU
Raleigh
MDW
Chicago
$183 Roundtrip, found 7 hours ago
$183
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, May 31 from Raleigh to Chicago, returning Tue, Jun 10, priced at $183 found 7 hours ago
Frontier Airlines
Sat, Apr 26 - Sat, May 10
RDU
Raleigh
MDW
Chicago
$188 Roundtrip, just found
$188
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 26 from Raleigh to Chicago, returning Sat, May 10, priced at $188 just found
Flights from Raleigh (RDU) to Chicago (MDW)
Origin airport
Raleigh - Durham Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$161
Distance
631 mi

Raleigh to Chicago Flights

The cheapest times to fly from Raleigh to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Raleigh to Chicago are during the month of July. You can find some of the cheapest flights from Raleigh to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Raleigh to Chicago

Sunday is one of the best days to book for cheap flights from Raleigh to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Raleigh to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Raleigh to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $81 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Raleigh to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Raleigh to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW) cost?
You can pick up cheap return tickets starting at $147 from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Frontier Airlines flight leaving RDU on May 7 2025 and touching down at MDW. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from RDU to MDW?
The cheapest flights from RDU to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
Hop on a direct flight with Southwest Airlines and head straight from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from RDU to MDW?
Currently, the cheapest airline operating one-way flights from RDU to MDW is Southwest Airlines. You can take off on this route from $81. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from RDU on May 25 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
Each day on average, 2 nonstop flights operate from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW). Choose the departure that best fits your schedule.
What are the most popular departure times for flights from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
Flights between RDU and MDW are their busiest at 6 AM. If you’re after a less crowded experience and possibly cheaper fares, choose a time outside the usual busy windows.
What day of the week has the most flights from RDU to MDW?
If you travel on a Thursday, you’ll get the biggest range of choices for flights from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW).
What is the earliest flight from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
The earliest flight jetting off from Raleigh - Durham Intl. Airport (RDU) is at around 6:30AM UTC-5. Board this plane and you’ll touch down at Midway Intl. Airport (MDW) at approximately 7:40AM UTC-6. The total time in the air is 2h 10m.
How long does it take to fly from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
It usually takes 2 hours and 7 minutes to fly the 630 mi from RDU to MDW.
What is the best time to fly from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
Opt for a flight from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Raleigh - Durham Intl. Airport (RDU)?
Hop on a direct flight from Raleigh - Durham Intl. Airport (RDU) to Chicago and touch down at O’Hare Intl. Airport (ORD). Another convenient arrival point to this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from RDU to MDW right before your trip is usually more expensive. But if there’s some wiggle room with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a RDU to MDW flight and hotel package?
Securing a RDU to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our extensive range of stays and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Raleigh - Durham Intl. Airport (RDU) to Midway Intl. Airport (MDW)?
If you booked your RDU to MDW flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

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*Available to One Key members.