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Cheap flights from Raleigh to Chicago from $65

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 4/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Raleigh to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:16 am - 6:37 pm
RDU
-
MDW
13h 21m
1 stop
Frontier Logo
6:00 am - 3:04 pm
MDW
-
RDU
8h 04m
1 stop
$162Frontier
Sat, May 2 - Tue, May 5
Frontier Logo
4:00 pm - 10:14 pm
RDU
-
MDW
7h 14m
1 stop
Frontier Logo
6:10 am - 3:04 pm
MDW
-
RDU
7h 54m
1 stop
$163Frontier
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
3:57 pm - 8:07 pm
RDU
-
MDW
5h 10m
1 stop
Frontier Logo
6:30 am - 3:04 pm
MDW
-
RDU
7h 34m
1 stop
$164Frontier
Mon, Apr 13 - Wed, Apr 15
Frontier Logo
3:57 pm - 8:07 pm
RDU
-
MDW
5h 10m
1 stop
Frontier Logo
5:05 am - 7:56 am
MDW
-
RDU
25h 51m
1 stop
$165Frontier
Thu, Apr 9 - Sun, Apr 12
Frontier Logo
4:00 pm - 10:14 pm
RDU
-
MDW
7h 14m
1 stop
Frontier Logo
9:04 am - 7:56 am
MDW
-
RDU
21h 52m
1 stop
$167Frontier
Wed, Apr 15 - Sun, Apr 19
Frontier Logo
3:42 pm - 10:19 pm
RDU
-
MDW
7h 37m
1 stop
Frontier Logo
2:15 pm - 11:25 pm
MDW
-
RDU
8h 10m
1 stop
$168Frontier
Mon, Apr 20 - Mon, Apr 27
Frontier Logo
3:49 pm - 10:26 pm
RDU
-
MDW
7h 37m
1 stop
Frontier Logo
2:15 pm - 7:56 am
MDW
-
RDU
16h 41m
2 stops
$169Frontier
Fri, Apr 17 - Wed, Apr 22
Frontier Logo
4:07 pm - 10:19 pm
RDU
-
MDW
7h 12m
1 stop
Frontier Logo
2:20 pm - 12:15 am
MDW
-
RDU
8h 55m
1 stop
$170Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:49 pm - 10:26 pm
RDU
-
MDW
7h 37m
1 stop
Frontier Logo
9:04 am - 7:56 am
MDW
-
RDU
21h 52m
1 stop
$171Frontier
Fri, Apr 17 - Sun, Apr 19
Frontier Logo
6:00 am - 6:37 pm
RDU
-
MDW
13h 37m
1 stop
Frontier Logo
6:00 am - 8:46 am
MDW
-
RDU
25h 46m
1 stop
$172Frontier
Sat, Apr 18 - Sun, Apr 26

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
May 2
RDU6:16 amRaleigh-Durham
13h 21m
1 stop
MDW6:37 pmChicago Midway
May 6
MDW6:00 amChicago Midway
8h 04m
1 stop
RDU3:04 pmRaleigh-Durham
$162
Frontier
Apr 21
RDU4:00 pmRaleigh-Durham
7h 14m
1 stop
MDW10:14 pmChicago Midway
Apr 28
MDW6:10 amChicago Midway
7h 54m
1 stop
RDU3:04 pmRaleigh-Durham
$163
Frontier
Apr 13
RDU3:57 pmRaleigh-Durham
5h 10m
1 stop
MDW8:07 pmChicago Midway
Apr 15
MDW6:30 amChicago Midway
7h 34m
1 stop
RDU3:04 pmRaleigh-Durham
$164

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
May 2
RDU3:55 pmRaleigh-Durham
2h 00m
MDW4:55 pmChicago Midway
May 4
MDW2:40 pmChicago Midway
1h 50m
RDU5:30 pmRaleigh-Durham
$180
Southwest
Apr 15
RDU6:40 pmRaleigh-Durham
2h 00m
MDW7:40 pmChicago Midway
Apr 18
MDW3:45 pmChicago Midway
1h 50m
RDU6:35 pmRaleigh-Durham
$187
Southwest
Jun 4
RDU7:35 pmRaleigh-Durham
2h 00m
MDW8:35 pmChicago Midway
Jun 6
MDW12:50 pmChicago Midway
1h 55m
RDU3:45 pmRaleigh-Durham
$193

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 March 10, 2026.
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

Cheapest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/2

6:16 am-6:37 pm

1 stop13h 21m

Chicago Midway

Tue 5/5

6:00 am-3:04 pm

1 stop8h 04m

$162

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 4/21

4:00 pm-10:14 pm

1 stop7h 14m

Chicago Midway

Tue 4/28

6:10 am-3:04 pm

1 stop7h 54m

$163
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 4/13

3:57 pm-8:07 pm

1 stop5h 10m

Chicago Midway

Wed 4/15

6:30 am-3:04 pm

1 stop7h 34m

$164

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 4/9

3:57 pm-8:07 pm

1 stop5h 10m

Chicago Midway

Sun 4/12

5:05 am-7:56 am

1 stop25h 51m

$165

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 4/15

4:00 pm-10:14 pm

1 stop7h 14m

Chicago Midway

Sun 4/19

9:04 am-7:56 am

1 stop21h 52m

$167

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 4/20

3:42 pm-10:19 pm

1 stop7h 37m

Chicago Midway

Mon 4/27

2:15 pm-11:25 pm

1 stop8h 10m

$168

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 4/17

3:49 pm-10:26 pm

1 stop7h 37m

Chicago Midway

Wed 4/22

2:15 pm-7:56 am

2 stops16h 41m

$169

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 5/8

4:07 pm-10:19 pm

1 stop7h 12m

Chicago Midway

Mon 5/11

2:20 pm-12:15 am

1 stop8h 55m

$170

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 4/17

3:49 pm-10:26 pm

1 stop7h 37m

Chicago Midway

Sun 4/19

9:04 am-7:56 am

1 stop21h 52m

$171

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 4/18

6:00 am-6:37 pm

1 stop13h 37m

Chicago Midway

Sun 4/26

6:00 am-8:46 am

1 stop25h 46m

$172

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 January is also very affordable. Most momondo users find prices during this month for around $243.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Raleigh. The lowest ticket price found for a Thursday departure recently was $331. 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 $392.

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 $309 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $365. 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 $341 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.

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

$176

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Raleigh in the past 72 hours is $176. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $304.
The fastest flight from Raleigh to Chicago Midway Airport takes 1h 50m
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 1h 50m, 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 $131Free CancellationRating
5.7
3,033 reviews
Search Frontier flights
DeltaPriceFrom $148Free CancellationRating
7.9
8,276 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,317 reviews
Search Southwest flights

  • Southwest Flights From Raleigh to Chicago Midway Airport

    Southwest operates around 9 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $309, but momondo users have found Southwest deals from Raleigh to Chicago Midway Airport from as low as $177 round-trip. Southwest has been scored 8.0/10 in 4,317 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
Valparaiso
Schererville
Munster
Crown Point
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

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