Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Raleigh to Chicago from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Raleigh to Chicago departing on 1/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Raleigh to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:19 pm - 12:02 am
RDU
-
MDW
5h 43m1 stop
Multiple Airlines Logo
1:20 pm - 11:51 pm
MDW
-
RDU
9h 31m1 stop
$127Multiple Airlines
Thu, Jan 15 - Tue, Jan 27
Frontier Logo
6:10 am - 11:45 am
RDU
-
MDW
6h 35m1 stop
Frontier Logo
5:01 pm - 12:11 am
MDW
-
RDU
6h 10m1 stop
$128Frontier
Thu, Feb 5 - Sun, Feb 8
Frontier Logo
6:10 am - 11:45 am
RDU
-
MDW
6h 35m1 stop
Frontier Logo
5:01 pm - 12:11 am
MDW
-
RDU
6h 10m1 stop
$129Frontier
Thu, Jan 22 - Sun, Jan 25
Frontier Logo
6:16 pm - 10:34 am
RDU
-
MDW
17h 18m1 stop
Frontier Logo
6:30 pm - 7:21 pm
MDW
-
RDU
23h 51m1 stop
$138Frontier
Mon, Jan 12 - Thu, Jan 15
Frontier Logo
10:20 am - 10:21 pm
RDU
-
MDW
13h 01m1 stop
Frontier Logo
4:31 pm - 1:58 pm
MDW
-
RDU
20h 27m1 stop
$141Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
6:16 pm - 10:17 pm
RDU
-
MDW
5h 01m1 stop
Frontier Logo
11:39 am - 10:43 pm
MDW
-
RDU
10h 04m1 stop
$143Frontier
Mon, Jan 12 - Wed, Jan 14
Frontier Logo
6:10 am - 11:45 am
RDU
-
MDW
6h 35m1 stop
Frontier Logo
5:01 pm - 12:11 am
MDW
-
RDU
6h 10m1 stop
$145Frontier
Thu, Jan 29 - Thu, Jan 29
Frontier Logo
3:54 pm - 6:54 pm
RDU
-
MDW
28h 00m1 stop
Frontier Logo
5:01 pm - 12:11 am
MDW
-
RDU
6h 10m1 stop
$146Frontier
Thu, Jan 15 - Thu, Jan 22
Frontier Logo
6:10 am - 10:31 am
RDU
-
MDW
5h 21m1 stop
Frontier Logo
8:28 am - 2:27 pm
MDW
-
RDU
4h 59m1 stop
$147Frontier
Wed, Jan 14 - Fri, Jan 16
Multiple Airlines Logo
7:19 pm - 12:02 am
RDU
-
MDW
5h 43m1 stop
Multiple Airlines Logo
8:22 am - 10:18 pm
MDW
-
RDU
12h 56m1 stop
$157Multiple Airlines
Thu, Jan 15 - Sat, Jan 17

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
Dec 25
RDU5:30 amRaleigh-Durham
2h 00m
MDW6:30 amChicago Midway
Dec 31
MDW10:00 amChicago Midway
2h 00m
RDU1:00 pmRaleigh-Durham
$177
Find similar
Southwest
Dec 25
RDU8:15 amRaleigh-Durham
4h 10m
1 stop
MDW11:25 amChicago Midway
Dec 31
MDW10:00 amChicago Midway
2h 00m
RDU1:00 pmRaleigh-Durham
$187
Find similar
Southwest
Dec 25
RDU11:10 amRaleigh-Durham
6h 25m
2 stops
MDW4:35 pmChicago Midway
Dec 31
MDW10:00 amChicago Midway
2h 00m
RDU1:00 pmRaleigh-Durham
$227
Find similar

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
Dec 15
RDU12:55 pmRaleigh-Durham
20h 51m
1 stop
MDW8:46 amChicago Midway
Dec 17
MDW2:49 pmChicago Midway
8h 23m
1 stop
RDU12:12 amRaleigh-Durham
$127
Find similar
Frontier
Feb 5
RDU6:10 amRaleigh-Durham
6h 35m
1 stop
MDW11:45 amChicago Midway
Feb 8
MDW5:01 pmChicago Midway
6h 10m
1 stop
RDU12:11 amRaleigh-Durham
$128
Find similar
Frontier
Jan 22
RDU6:10 amRaleigh-Durham
6h 35m
1 stop
MDW11:45 amChicago Midway
Jan 25
MDW5:01 pmChicago Midway
6h 10m
1 stop
RDU12:11 amRaleigh-Durham
$129
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Raleigh to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 9, 2025.
Use the filters below to find and compare flights from Raleigh to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/15

7:19 pm-12:02 am

1 stop5h 43m

Chicago Midway

Tue 1/27

1:20 pm-11:51 pm

1 stop9h 31m

$127

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/5

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

Sun 2/8

5:01 pm-12:11 am

1 stop6h 10m

$128

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/22

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

Sun 1/25

5:01 pm-12:11 am

1 stop6h 10m

$129

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 1/12

6:16 pm-10:34 am

1 stop17h 18m

Chicago Midway

Thu 1/15

6:30 pm-7:21 pm

1 stop23h 51m

$138

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 1/9

10:20 am-10:21 pm

1 stop13h 01m

Chicago Midway

Mon 1/12

4:31 pm-1:58 pm

1 stop20h 27m

$141

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 1/12

6:16 pm-10:17 pm

1 stop5h 01m

Chicago Midway

Wed 1/14

11:39 am-10:43 pm

1 stop10h 04m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/29

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

Thu 1/29

5:01 pm-12:11 am

1 stop6h 10m

$145

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/15

3:54 pm-6:54 pm

1 stop28h 00m

Chicago Midway

Thu 1/22

5:01 pm-12:11 am

1 stop6h 10m

$146

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/14

6:10 am-10:31 am

1 stop5h 21m

Chicago Midway

Fri 1/16

8:28 am-2:27 pm

1 stop4h 59m

$147

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/15

7:19 pm-12:02 am

1 stop5h 43m

Chicago Midway

Sat 1/17

8:22 am-10:18 pm

1 stop12h 56m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Raleigh to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Raleigh, with most prices found around $237. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Raleigh during the month February is also very affordable. Most momondo users find prices during this month for around $239.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Raleigh. The lowest ticket price found for a Friday departure recently was $346. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Raleigh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $390.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Raleigh in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $330 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $370. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Raleigh-Durham to Chicago Midway flight route?

Fly from Raleigh-Durham to Chicago Midway for the best Raleigh-Durham - Chicago Midway flight prices

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

You are more likely to see cheaper flights to Chicago Midway Airport from Raleigh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $306 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Raleigh for as low as $171 on momondo.

What cabin class options are available on Raleigh-Durham to Chicago Midway flights?

There is only 1 cabin class available to choose from on Raleigh-Durham to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Raleigh to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Raleigh to Chicago Midway Airport.

How have Raleigh to Chicago Midway Airport flight prices changed over time?

When to book flights from Raleigh to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Raleigh to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Raleigh to Chicago Midway Airport (RDU to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Raleigh to Chicago Midway Airport

Best Price Found

$115

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Raleigh in the past 72 hours is $115. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $307.
The fastest flight from Raleigh to Chicago Midway Airport takes 1h 55m
Direct flights go from Raleigh to Chicago Midway Airport every day.
Search flight deals

  • How far is Raleigh-Durham to Chicago Midway by plane?

    The distance between Raleigh-Durham and Chicago Midway is about 641.7 mi. Flights usually cover this in 2h 00m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Raleigh-Durham Airport to Chicago Midway Airport?

    Prices for flights from Raleigh-Durham Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Raleigh-Durham Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Raleigh-Durham Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Raleigh-Durham Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Raleigh to Chicago Midway Airport?

  • What is the most popular airline from Raleigh to Chicago Midway Airport?

Best airlines flying from Raleigh to Chicago Midway Airport

Compare and see reviews for airlines that fly from Raleigh to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $120Free CancellationRating
5.8
3,085 reviews
Search Frontier flights
DeltaPriceFrom $157Free CancellationRating
7.9
8,011 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

  • Southwest Flights From Raleigh to Chicago Midway Airport

    Southwest operates around 12 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $314, but momondo users have found Southwest deals from Raleigh to Chicago Midway Airport from as low as $177 round-trip. Southwest has been scored 7.9/10 in 4,252 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Raleigh to Chicago?

It is quick and easy to find Raleigh to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Raleigh to Chicago with flexible booking policies on momondo?

All flight searches from Raleigh to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Raleigh to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Raleigh.

I’m not ready to book a flight from Raleigh to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Raleigh are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/8
Thu 1/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago