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Cheap flights from Raleigh to Chicago from $75

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 9/25. 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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Find the cheapest flights from Raleigh to Chicago

Cheap round-trip flights

Southwest Logo
6:00 am - 6:55 amRDU-MDW
1h 55mnonstop
Southwest Logo
10:10 am - 1:00 pmMDW-RDU
1h 50mnonstop
$139Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Frontier Logo
5:10 pm - 11:20 pmRDU-MDW
7h 10m1 stop
Frontier Logo
5:10 am - 5:15 pmMDW-RDU
11h 05m1 stop
$140Frontier
Find Deal
Sat, Oct 25 - Mon, Oct 27
Frontier Logo
7:15 pm - 11:46 pmRDU-MDW
5h 31m1 stop
Frontier Logo
10:49 am - 6:08 pmMDW-RDU
6h 19m1 stop
$143Frontier
Find Deal
Fri, Oct 17 - Thu, Oct 23
Frontier Logo
6:38 pm - 11:41 pmRDU-MDW
6h 03m1 stop
Frontier Logo
6:21 am - 5:11 pmMDW-RDU
9h 50m1 stop
$144Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Frontier Logo
7:15 pm - 11:46 pmRDU-MDW
5h 31m1 stop
Frontier Logo
5:20 am - 3:41 pmMDW-RDU
9h 21m1 stop
$145Frontier
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
5:39 pm - 12:36 amRDU-MDW
7h 57m1 stop
Frontier Logo
12:03 pm - 6:20 pmMDW-RDU
5h 17m1 stop
$146Frontier
Find Deal
Thu, Oct 23 - Fri, Oct 24
Southwest Logo
6:35 am - 7:30 amRDU-MDW
1h 55mnonstop
Southwest Logo
5:45 pm - 8:35 pmMDW-RDU
1h 50mnonstop
$149Southwest
Find Deal
Sat, Oct 11 - Sat, Oct 18
Frontier Logo
12:30 pm - 1:38 pmRDU-MDW
26h 08m1 stop
Frontier Logo
5:20 pm - 10:22 amMDW-RDU
16h 02m1 stop
$154Frontier
Find Deal
Tue, Oct 21 - Sat, Oct 25
Frontier Logo
7:15 pm - 11:46 pmRDU-MDW
5h 31m1 stop
Frontier Logo
1:56 pm - 4:39 pmMDW-RDU
25h 43m1 stop
$156Frontier
Find Deal
Thu, Oct 23 - Tue, Oct 28
Delta Logo
5:44 am - 8:40 amRDU-MDW
3h 56m1 stop
Delta Logo
6:23 pm - 10:58 pmMDW-RDU
3h 35m1 stop
$197Delta
Find Deal
Wed, Oct 15 - Tue, Oct 21

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
Oct 15
RDU6:00 amRaleigh-Durham
1h 55m
MDW6:55 amChicago Midway
Oct 22
MDW10:10 amChicago Midway
1h 50m
RDU1:00 pmRaleigh-Durham
$139
Find similar
Southwest
Oct 11
RDU6:35 amRaleigh-Durham
1h 55m
MDW7:30 amChicago Midway
Oct 18
MDW5:45 pmChicago Midway
1h 50m
RDU8:35 pmRaleigh-Durham
$149
Find similar
Southwest
Oct 16
RDU5:45 amRaleigh-Durham
2h 00m
MDW6:45 amChicago Midway
Oct 18
MDW9:55 amChicago Midway
1h 50m
RDU12:45 pmRaleigh-Durham
$158
Find similar

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
Oct 25
RDU5:10 pmRaleigh-Durham
7h 10m
1 stop
MDW11:20 pmChicago Midway
Oct 27
MDW5:10 amChicago Midway
11h 05m
1 stop
RDU5:15 pmRaleigh-Durham
$140
Find similar
Frontier
Oct 17
RDU7:15 pmRaleigh-Durham
5h 31m
1 stop
MDW11:46 pmChicago Midway
Oct 23
MDW10:49 amChicago Midway
6h 19m
1 stop
RDU6:08 pmRaleigh-Durham
$143
Find similar
Frontier
Oct 2
RDU6:38 pmRaleigh-Durham
6h 03m
1 stop
MDW11:41 pmChicago Midway
Oct 5
MDW6:21 amChicago Midway
9h 50m
1 stop
RDU5:11 pmRaleigh-Durham
$144
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 September 17, 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

Wed 10/15

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Wed 10/22

10:10 am-1:00 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/25

5:10 pm-11:20 pm

1 stop7h 10m

Chicago Midway

Mon 10/27

5:10 am-5:15 pm

1 stop11h 05m

$140

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 10/17

7:15 pm-11:46 pm

1 stop5h 31m

Chicago Midway

Thu 10/23

10:49 am-6:08 pm

1 stop6h 19m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/2

6:38 pm-11:41 pm

1 stop6h 03m

Chicago Midway

Sun 10/5

6:21 am-5:11 pm

1 stop9h 50m

$144

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/23

7:15 pm-11:46 pm

1 stop5h 31m

Chicago Midway

Sun 10/26

5:20 am-3:41 pm

1 stop9h 21m

$145

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/23

5:39 pm-12:36 am

1 stop7h 57m

Chicago Midway

Fri 10/24

12:03 pm-6:20 pm

1 stop5h 17m

$146

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

6:35 am-7:30 am

Nonstop1h 55m

Chicago Midway

Sat 10/18

5:45 pm-8:35 pm

Nonstop1h 50m

$149

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 10/21

12:30 pm-1:38 pm

1 stop26h 08m

Chicago Midway

Sat 10/25

5:20 pm-10:22 am

1 stop16h 02m

$154

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/23

7:15 pm-11:46 pm

1 stop5h 31m

Chicago Midway

Tue 10/28

1:56 pm-4:39 pm

1 stop25h 43m

$156

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 10/15

5:44 am-8:40 am

1 stop3h 56m

Chicago Midway

Tue 10/21

6:23 pm-10:58 pm

1 stop3h 35m

$197

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Raleigh, with most prices found around $239. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Raleigh during the month October is also very affordable. Most momondo users find prices during this month for around $257.

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 $354. 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 $407.

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 $333 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $376. 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 $303 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 $202 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?

You could potentially save up to 6% on your flight if you consider stops on a Raleigh to Chicago Midway Airport flight.

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

$138

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 $138. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $210.
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 1h 55m, 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 $108Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
DeltaPriceFrom $157Free CancellationRating
7.9
7,961 reviews
Search Delta flights
SouthwestPriceFrom $181Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $197Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

  • Southwest Flights From Raleigh to Chicago Midway Airport

    Southwest operates around 15 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $320, but momondo users have found Southwest deals from Raleigh to Chicago Midway Airport from as low as $181 round-trip. Southwest has been scored 8.0/10 in 4,242 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
Lansing
Portage
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

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