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Cheap flights from Raleigh to Chicago from $61

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 1/26. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:53 pm - 6:08 pmRDU-MDW
6h 15m1 stop
Frontier Logo
3:52 pm - 4:44 pmMDW-RDU
23h 52m1 stop
$128Frontier
Find Deal
Thu, Dec 4 - Fri, Dec 12
Frontier Logo
3:21 pm - 9:53 pmRDU-MDW
7h 32m1 stop
Frontier Logo
7:23 pm - 10:16 amMDW-RDU
13h 53m1 stop
$133Frontier
Find Deal
Thu, Dec 4 - Thu, Dec 11
Frontier Logo
11:13 am - 7:42 pmRDU-MDW
9h 29m1 stop
Frontier Logo
6:15 am - 12:08 pmMDW-RDU
4h 53m1 stop
$138Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
1:40 pm - 2:45 pmRDU-MDW
2h 05mnonstop
Southwest Logo
6:05 pm - 8:55 pmMDW-RDU
1h 50mnonstop
$139Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Frontier Logo
11:13 am - 7:42 pmRDU-MDW
9h 29m1 stop
Frontier Logo
6:37 pm - 8:23 amMDW-RDU
12h 46m1 stop
$142Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
8:14 pm - 9:58 pmRDU-MDW
26h 44m1 stop
Frontier Logo
3:52 pm - 4:44 pmMDW-RDU
23h 52m1 stop
$146Frontier
Find Deal
Wed, Dec 10 - Fri, Dec 12
Southwest Logo
5:10 pm - 6:15 pmRDU-MDW
2h 05mnonstop
Southwest Logo
9:45 am - 12:40 pmMDW-RDU
1h 55mnonstop
$158Southwest
Find Deal
Sat, Dec 6 - Sun, Dec 7
Delta Logo
5:29 am - 8:54 amRDU-MDW
4h 25m1 stop
Delta Logo
6:00 am - 11:34 amMDW-RDU
4h 34m1 stop
$187Delta
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Thu, Dec 11 - Sat, Dec 13
Multiple Airlines Logo
11:13 am - 7:42 pmRDU-MDW
9h 29m1 stop
Multiple Airlines Logo
3:52 pm - 9:47 amMDW-RDU
16h 55m2 stops
$221Multiple Airlines
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Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
8:31 am - 2:33 pmRDU-MDW
7h 02m1 stop
Multiple Airlines Logo
1:37 pm - 9:47 amMDW-RDU
19h 10m2 stops
$226Multiple Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
Dec 2
RDU1:40 pmRaleigh-Durham
2h 05m
MDW2:45 pmChicago Midway
Dec 9
MDW6:05 pmChicago Midway
1h 50m
RDU8:55 pmRaleigh-Durham
$139
Find similar
Southwest
Dec 6
RDU5:10 pmRaleigh-Durham
2h 05m
MDW6:15 pmChicago Midway
Dec 7
MDW9:45 amChicago Midway
1h 55m
RDU12:40 pmRaleigh-Durham
$158
Find similar
Southwest
Dec 4
RDU5:30 amRaleigh-Durham
2h 00m
MDW6:30 amChicago Midway
Dec 11
MDW10:00 amChicago Midway
2h 00m
RDU1:00 pmRaleigh-Durham
$177
Find similar

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
Dec 4
RDU12:53 pmRaleigh-Durham
6h 15m
1 stop
MDW6:08 pmChicago Midway
Dec 12
MDW3:52 pmChicago Midway
23h 52m
1 stop
RDU4:44 pmRaleigh-Durham
$128
Find similar
Frontier
Dec 4
RDU3:21 pmRaleigh-Durham
7h 32m
1 stop
MDW9:53 pmChicago Midway
Dec 11
MDW7:23 pmChicago Midway
13h 53m
1 stop
RDU10:16 amRaleigh-Durham
$133
Find similar
Frontier
Dec 5
RDU11:13 amRaleigh-Durham
9h 29m
1 stop
MDW7:42 pmChicago Midway
Dec 7
MDW6:15 amChicago Midway
4h 53m
1 stop
RDU12:08 pmRaleigh-Durham
$138
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 November 3, 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 12/4

12:53 pm-6:08 pm

1 stop6h 15m

Chicago Midway

Fri 12/12

3:52 pm-4:44 pm

1 stop23h 52m

$128

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/4

3:21 pm-9:53 pm

1 stop7h 32m

Chicago Midway

Thu 12/11

7:23 pm-10:16 am

1 stop13h 53m

$133

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/5

11:13 am-7:42 pm

1 stop9h 29m

Chicago Midway

Sun 12/7

6:15 am-12:08 pm

1 stop4h 53m

$138

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 12/2

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Tue 12/9

6:05 pm-8:55 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/12

11:13 am-7:42 pm

1 stop9h 29m

Chicago Midway

Sun 12/14

6:37 pm-8:23 am

1 stop12h 46m

$142

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 12/10

8:14 pm-9:58 pm

1 stop26h 44m

Chicago Midway

Fri 12/12

3:52 pm-4:44 pm

1 stop23h 52m

$146

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Sun 12/7

9:45 am-12:40 pm

Nonstop1h 55m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/11

5:29 am-8:54 am

1 stop4h 25m

Chicago Midway

Sat 12/13

6:00 am-11:34 am

1 stop4h 34m

$187

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/12

11:13 am-7:42 pm

1 stop9h 29m

Chicago Midway

Mon 12/15

3:52 pm-9:47 am

2 stops16h 55m

$221

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 11/14

8:31 am-2:33 pm

1 stop7h 02m

Chicago Midway

Mon 11/17

1:37 pm-9:47 am

2 stops19h 10m

$226

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 $246.

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 $349. 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 $398.

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 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 $305 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 $242 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

$128

Fastest flight time

2h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Raleigh in the past 72 hours is $128. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $263.
The fastest flight from Raleigh to Chicago Midway Airport takes 2h 00m
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
3,117 reviews
Search Frontier flights
DeltaPriceFrom $157Free CancellationRating
7.9
8,001 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • Southwest Flights From Raleigh to Chicago Midway Airport

    Southwest operates around 18 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $317, 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 4,238 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

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