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Cheap flights from Raleigh to Chicago from $60

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 12/13. 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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Cheap round-trip flights

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Frontier Logo
12:55 pm - 8:46 amRDU-MDW
20h 51m1 stop
Frontier Logo
2:49 pm - 12:12 amMDW-RDU
8h 23m1 stop
$128Frontier
Find Deal
Mon, Dec 15 - Tue, Dec 16
Frontier Logo
12:55 pm - 10:12 pmRDU-MDW
10h 17m1 stop
Frontier Logo
2:49 pm - 12:12 amMDW-RDU
8h 23m1 stop
$129Frontier
Find Deal
Mon, Dec 15 - Wed, Dec 17
Frontier Logo
5:45 am - 9:22 pmRDU-MDW
16h 37m1 stop
Frontier Logo
2:49 pm - 12:12 amMDW-RDU
8h 23m1 stop
$130Frontier
Find Deal
Sat, Dec 13 - Tue, Dec 16
Frontier Logo
5:45 am - 9:22 pmRDU-MDW
16h 37m1 stop
Frontier Logo
2:49 pm - 12:12 amMDW-RDU
8h 23m1 stop
$131Frontier
Find Deal
Sat, Dec 13 - Wed, Dec 17
Frontier Logo
5:45 am - 9:22 pmRDU-MDW
16h 37m1 stop
Frontier Logo
6:15 am - 12:12 amMDW-RDU
16h 57m1 stop
$132Frontier
Find Deal
Sat, Dec 13 - Mon, Dec 15
Frontier Logo
5:45 am - 9:22 pmRDU-MDW
16h 37m1 stop
Frontier Logo
6:15 am - 12:12 amMDW-RDU
16h 57m1 stop
$133Frontier
Find Deal
Sat, Dec 13 - Mon, Dec 15
Frontier Logo
12:55 pm - 8:46 amRDU-MDW
20h 51m1 stop
Frontier Logo
6:12 am - 12:13 amMDW-RDU
17h 01m1 stop
$134Frontier
Find Deal
Mon, Dec 15 - Thu, Dec 18
Multiple Airlines Logo
7:19 pm - 12:02 amRDU-MDW
5h 43m1 stop
Multiple Airlines Logo
8:28 am - 2:27 pmMDW-RDU
4h 59m1 stop
$135Multiple Airlines
Find Deal
Thu, Jan 15 - Fri, Jan 16
Frontier Logo
5:45 am - 9:22 pmRDU-MDW
16h 37m1 stop
Frontier Logo
6:12 am - 12:13 amMDW-RDU
17h 01m1 stop
$136Frontier
Find Deal
Sat, Dec 13 - Thu, Dec 18
Frontier Logo
5:45 am - 9:22 pmRDU-MDW
16h 37m1 stop
Frontier Logo
6:12 am - 12:13 amMDW-RDU
17h 01m1 stop
$137Frontier
Find Deal
Sat, Dec 13 - Thu, Dec 18

Frontier flights from Raleigh to Chicago Midway Airport

Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
Frontier
Dec 15
RDU12:55 pmRaleigh-Durham
20h 51m
1 stop
MDW8:46 amChicago Midway
Dec 16
MDW2:49 pmChicago Midway
8h 23m
1 stop
RDU12:12 amRaleigh-Durham
$128
Find similar
Frontier
Dec 15
RDU12:55 pmRaleigh-Durham
10h 17m
1 stop
MDW10:12 pmChicago Midway
Dec 17
MDW2:49 pmChicago Midway
8h 23m
1 stop
RDU12:12 amRaleigh-Durham
$129
Find similar
Frontier
Dec 13
RDU5:45 amRaleigh-Durham
16h 37m
1 stop
MDW9:22 pmChicago Midway
Dec 16
MDW2:49 pmChicago Midway
8h 23m
1 stop
RDU12:12 amRaleigh-Durham
$130
Find similar

Delta flights from Raleigh to Chicago Midway Airport

Our best Delta deals on Raleigh to Chicago Midway Airport flight tickets
Delta
Dec 16
RDU5:29 amRaleigh-Durham
4h 25m
1 stop
MDW8:54 amChicago Midway
Dec 16
MDW1:14 pmChicago Midway
3h 26m
1 stop
RDU5:40 pmRaleigh-Durham
$178
Find similar
Delta
Dec 2
RDU5:29 amRaleigh-Durham
4h 25m
1 stop
MDW8:54 amChicago Midway
Dec 9
MDW10:49 amChicago Midway
4h 58m
1 stop
RDU4:47 pmRaleigh-Durham
$304
Find similar
Delta
Dec 6
RDU6:00 amRaleigh-Durham
4h 54m
1 stop
MDW9:54 amChicago Midway
Dec 6
MDW4:29 pmChicago Midway
4h 46m
1 stop
RDU10:15 pmRaleigh-Durham
$359
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 25, 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

Mon 12/15

12:55 pm-8:46 am

1 stop20h 51m

Chicago Midway

Tue 12/16

2:49 pm-12:12 am

1 stop8h 23m

$128

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 12/15

12:55 pm-10:12 pm

1 stop10h 17m

Chicago Midway

Wed 12/17

2:49 pm-12:12 am

1 stop8h 23m

$129

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:45 am-9:22 pm

1 stop16h 37m

Chicago Midway

Tue 12/16

2:49 pm-12:12 am

1 stop8h 23m

$130

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:45 am-9:22 pm

1 stop16h 37m

Chicago Midway

Wed 12/17

2:49 pm-12:12 am

1 stop8h 23m

$131

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:45 am-9:22 pm

1 stop16h 37m

Chicago Midway

Mon 12/15

6:15 am-12:12 am

1 stop16h 57m

$132

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:45 am-9:22 pm

1 stop16h 37m

Chicago Midway

Mon 12/15

6:15 am-12:12 am

1 stop16h 57m

$133

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 12/15

12:55 pm-8:46 am

1 stop20h 51m

Chicago Midway

Thu 12/18

6:12 am-12:13 am

1 stop17h 01m

$134

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/15

7:19 pm-12:02 am

1 stop5h 43m

Chicago Midway

Fri 1/16

8:28 am-2:27 pm

1 stop4h 59m

$135

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:45 am-9:22 pm

1 stop16h 37m

Chicago Midway

Thu 12/18

6:12 am-12:13 am

1 stop17h 01m

$136

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:45 am-9:22 pm

1 stop16h 37m

Chicago Midway

Thu 12/18

6:12 am-12:13 am

1 stop17h 01m

$137

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 $239.

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 $304 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

$108

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 $108. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $286.
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 10m, 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
3,097 reviews
Search Frontier flights
DeltaPriceFrom $157Free CancellationRating
7.9
7,998 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,252 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 $315, 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 4,252 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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