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Cheap flights from Raleigh to Chicago from $101

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 7/21. 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
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
Sat, May 16 - Tue, May 19
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
Wed, Jun 3 - Tue, Jun 9
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
Tue, Jul 14 - Sat, Jul 18
Frontier Logo
6:15 am - 11:09 am
RDU
-
MDW
5h 54m
1 stop
Frontier Logo
12:27 pm - 12:33 am
MDW
-
RDU
11h 06m
1 stop
$205Frontier
Wed, May 20 - Tue, May 26
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
Sat, May 16 - Tue, May 19
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 14 - Sun, May 17
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
Thu, May 28 - Mon, Jun 1
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 10 - Wed, Jun 17
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
Wed, Jun 24 - Sat, Jun 27
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
Sat, May 23 - Tue, May 26

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
May 16
RDU12:23 pmRaleigh-Durham
10h 39m
1 stop
MDW10:02 pmChicago Midway
May 19
MDW6:00 amChicago Midway
5h 04m
1 stop
RDU12:04 pmRaleigh-Durham
$201
Frontier
Jul 14
RDU6:15 amRaleigh-Durham
5h 52m
1 stop
MDW11:07 amChicago Midway
Jul 18
MDW12:11 pmChicago Midway
11h 14m
1 stop
RDU12:25 amRaleigh-Durham
$204
Frontier
Jun 6
RDU11:56 amRaleigh-Durham
11h 06m
1 stop
MDW10:02 pmChicago Midway
Jun 14
MDW6:00 amChicago Midway
4h 59m
1 stop
RDU11:59 amRaleigh-Durham
$205

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
Jun 2
RDU6:40 pmRaleigh-Durham
2h 00m
MDW7:40 pmChicago Midway
Jun 3
MDW7:40 amChicago Midway
1h 50m
RDU10:30 amRaleigh-Durham
$237
Southwest
Jun 2
RDU11:25 amRaleigh-Durham
6h 20m
1 stop
MDW4:45 pmChicago Midway
Jun 3
MDW7:40 amChicago Midway
1h 50m
RDU10:30 amRaleigh-Durham
$247
Southwest
May 23
RDU3:55 pmRaleigh-Durham
2h 00m
MDW4:55 pmChicago Midway
May 26
MDW7:40 amChicago Midway
1h 50m
RDU10:30 amRaleigh-Durham
$251

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 May 4, 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 5/16

12:23 pm-10:02 pm

1 stop10h 39m

Chicago Midway

Tue 5/19

6:00 am-12:04 pm

1 stop5h 04m

$201

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/3

10:03 pm-10:02 pm

2 stops24h 59m

Chicago Midway

Tue 6/9

6:00 am-12:29 am

1 stop17h 29m

$203

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 7/14

6:15 am-11:07 am

1 stop5h 52m

Chicago Midway

Sat 7/18

12:11 pm-12:25 am

1 stop11h 14m

$204

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 5/20

6:15 am-11:09 am

1 stop5h 54m

Chicago Midway

Tue 5/26

12:27 pm-12:33 am

1 stop11h 06m

$205

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/16

12:23 pm-10:02 pm

1 stop10h 39m

Chicago Midway

Tue 5/19

6:00 am-12:04 pm

1 stop5h 04m

$206

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 5/14

6:15 am-11:09 am

1 stop5h 54m

Chicago Midway

Sun 5/17

12:19 pm-12:24 am

1 stop11h 05m

$207

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 5/28

12:54 pm-10:02 pm

1 stop10h 08m

Chicago Midway

Mon 6/1

6:00 am-7:08 pm

2 stops12h 08m

$208

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/10

6:15 am-11:09 am

1 stop5h 54m

Chicago Midway

Wed 6/17

12:04 pm-12:21 am

1 stop11h 17m

$209
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/24

6:15 am-11:09 am

1 stop5h 54m

Chicago Midway

Sat 6/27

4:10 pm-11:50 pm

1 stop6h 40m

$210

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/23

11:56 am-10:02 pm

1 stop11h 06m

Chicago Midway

Tue 5/26

6:00 am-11:59 am

1 stop4h 59m

$211

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 typical price of a round-trip flight between Raleigh and Chicago Midway Airport?

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 $235. 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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Raleigh. The lowest ticket price found for a Wednesday departure recently was $329. 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 $428.

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 $296 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $380. 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 from Raleigh 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 $347 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.

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

$179

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 $179. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $339.
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

Frequently asked questions about flying from Raleigh to Chicago Midway Airport

  • 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 $142Free CancellationRating
5.6
2,966 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
7.9
4,310 reviews
Search Southwest flights

  • Southwest Flights From Raleigh to Chicago Midway Airport

    Southwest operates around 14 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $310, 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 4,310 reviews.

Traveling to a place near Chicago?

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