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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 2/3. 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
7:10 am - 12:05 pm
RDU
-
MDW
5h 55m1 stop
Frontier Logo
7:00 am - 7:35 pm
MDW
-
RDU
11h 35m1 stop
$139Frontier
Wed, Jan 28 - Wed, Feb 18
Frontier Logo
1:11 pm - 2:26 pm
RDU
-
MDW
26h 15m1 stop
Frontier Logo
8:00 am - 8:37 am
MDW
-
RDU
23h 37m1 stop
$140Frontier
Thu, Feb 19 - Sat, Feb 21
Frontier Logo
6:10 am - 6:38 pm
RDU
-
MDW
13h 28m1 stop
Frontier Logo
6:00 am - 4:15 pm
MDW
-
RDU
9h 15m1 stop
$148Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
10:38 am - 9:12 pm
RDU
-
MDW
11h 34m1 stop
Frontier Logo
9:22 pm - 4:59 pm
MDW
-
RDU
18h 37m1 stop
$150Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
8:47 am - 11:32 pm
RDU
-
MDW
15h 45m1 stop
Frontier Logo
11:19 am - 7:52 am
MDW
-
RDU
19h 33m1 stop
$151Frontier
Sat, Mar 14 - Tue, Mar 17
Frontier Logo
6:25 am - 7:07 pm
RDU
-
MDW
13h 42m1 stop
Frontier Logo
7:30 am - 12:10 am
MDW
-
RDU
15h 40m1 stop
$153Frontier
Tue, Feb 24 - Tue, Mar 3
Frontier Logo
6:10 am - 9:08 pm
RDU
-
MDW
15h 58m1 stop
Frontier Logo
2:19 pm - 12:10 am
MDW
-
RDU
8h 51m1 stop
$154Frontier
Sat, Feb 14 - Mon, Feb 16
Frontier Logo
7:10 am - 12:05 pm
RDU
-
MDW
5h 55m1 stop
Frontier Logo
1:20 pm - 11:51 pm
MDW
-
RDU
9h 31m1 stop
$156Frontier
Wed, Jan 21 - Wed, Jan 28
Frontier Logo
6:10 am - 11:45 am
RDU
-
MDW
6h 35m1 stop
Frontier Logo
1:20 pm - 11:51 pm
MDW
-
RDU
9h 31m1 stop
$159Frontier
Sun, Feb 1 - Wed, Feb 4
Frontier Logo
6:10 am - 10:25 pm
RDU
-
MDW
17h 15m1 stop
Frontier Logo
6:00 am - 3:45 pm
MDW
-
RDU
8h 45m1 stop
$160Frontier
Fri, Feb 13 - Sun, Feb 15

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
Jan 28
RDU7:10 amRaleigh-Durham
5h 55m
1 stop
MDW12:05 pmChicago Midway
Feb 18
MDW7:00 amChicago Midway
11h 35m
1 stop
RDU7:35 pmRaleigh-Durham
$139
Frontier
Feb 19
RDU1:11 pmRaleigh-Durham
26h 15m
1 stop
MDW2:26 pmChicago Midway
Feb 21
MDW8:00 amChicago Midway
23h 37m
1 stop
RDU8:37 amRaleigh-Durham
$140
Frontier
Feb 27
RDU6:10 amRaleigh-Durham
13h 28m
1 stop
MDW6:38 pmChicago Midway
Mar 2
MDW6:00 amChicago Midway
9h 15m
1 stop
RDU4:15 pmRaleigh-Durham
$148

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
Apr 7
RDU6:45 pmRaleigh-Durham
4h 05m
1 stop
MDW9:50 pmChicago Midway
Apr 11
MDW7:25 amChicago Midway
7h 55m
1 stop
RDU4:20 pmRaleigh-Durham
$231
Southwest
Mar 14
RDU7:05 pmRaleigh-Durham
2h 05m
MDW8:10 pmChicago Midway
Mar 16
MDW3:45 pmChicago Midway
6h 40m
1 stop
RDU11:25 pmRaleigh-Durham
$234

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 January 12, 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

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/28

7:10 am-12:05 pm

1 stop5h 55m

Chicago Midway

Wed 2/18

7:00 am-7:35 pm

1 stop11h 35m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/19

1:11 pm-2:26 pm

1 stop26h 15m

Chicago Midway

Sat 2/21

8:00 am-8:37 am

1 stop23h 37m

$140

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 2/27

6:10 am-6:38 pm

1 stop13h 28m

Chicago Midway

Mon 3/2

6:00 am-4:15 pm

1 stop9h 15m

$148

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/19

10:38 am-9:12 pm

1 stop11h 34m

Chicago Midway

Mon 2/23

9:22 pm-4:59 pm

1 stop18h 37m

$150

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 3/14

8:47 am-11:32 pm

1 stop15h 45m

Chicago Midway

Tue 3/17

11:19 am-7:52 am

1 stop19h 33m

$151

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 2/24

6:25 am-7:07 pm

1 stop13h 42m

Chicago Midway

Tue 3/3

7:30 am-12:10 am

1 stop15h 40m

$153

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 2/14

6:10 am-9:08 pm

1 stop15h 58m

Chicago Midway

Mon 2/16

2:19 pm-12:10 am

1 stop8h 51m

$154

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/21

7:10 am-12:05 pm

1 stop5h 55m

Chicago Midway

Wed 1/28

1:20 pm-11:51 pm

1 stop9h 31m

$156

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 2/1

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

Wed 2/4

1:20 pm-11:51 pm

1 stop9h 31m

$159

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 2/13

6:10 am-10:25 pm

1 stop17h 15m

Chicago Midway

Sun 2/15

6:00 am-3:45 pm

1 stop8h 45m

$160

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 February is also very affordable. Most momondo users find prices during this month for around $242.

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 $341. 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 $380.

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 $322 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $367. 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 $298 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

$201

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 $201. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $290.
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 $126Free CancellationRating
5.7
3,055 reviews
Search Frontier flights
DeltaPriceFrom $157Free CancellationRating
7.9
8,034 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

  • Southwest Flights From Raleigh to Chicago Midway Airport

    Southwest operates around 16 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 8.0/10 in 4,255 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
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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