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Cheap flights from Raleigh to Chicago from $84

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 10/10. 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 (RDU-MDW)

Cheap round-trip flights

Southwest Logo
6:35 am - 7:30 amRDU-MDW
1h 55mnonstop
Southwest Logo
6:05 pm - 8:55 pmMDW-RDU
1h 50mnonstop
$139Southwest
Find Deal
Sat, Nov 1 - Tue, Nov 11
Frontier Logo
7:15 pm - 11:25 pmRDU-MDW
5h 10m1 stop
Frontier Logo
6:20 am - 6:20 pmMDW-RDU
11h 00m1 stop
$143Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
8:49 am - 5:27 pmRDU-MDW
9h 38m1 stop
Frontier Logo
8:25 am - 1:41 pmMDW-RDU
4h 16m1 stop
$144Frontier
Find Deal
Mon, Oct 20 - Thu, Oct 23
Frontier Logo
6:05 pm - 11:44 amRDU-MDW
18h 39m1 stop
Frontier Logo
6:15 am - 6:50 pmMDW-RDU
11h 35m1 stop
$148Frontier
Find Deal
Sat, Oct 11 - Sat, Oct 18
Frontier Logo
6:42 pm - 4:09 pmRDU-MDW
22h 27m1 stop
Frontier Logo
8:05 am - 3:37 pmMDW-RDU
6h 32m1 stop
$149Frontier
Find Deal
Fri, Oct 10 - Tue, Oct 14
Frontier Logo
6:22 am - 4:00 pmRDU-MDW
10h 38m1 stop
Frontier Logo
8:15 am - 1:38 pmMDW-RDU
4h 23m1 stop
$153Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
6:06 pm - 12:44 pmRDU-MDW
19h 38m1 stop
Frontier Logo
10:51 am - 9:53 amMDW-RDU
22h 02m1 stop
$154Frontier
Find Deal
Sat, Sep 6 - Sat, Sep 13
Southwest Logo
1:35 pm - 2:30 pmRDU-MDW
1h 55mnonstop
Southwest Logo
1:50 pm - 4:45 pmMDW-RDU
1h 55mnonstop
$158Southwest
Find Deal
Tue, Sep 23 - Fri, Sep 26
Southwest Logo
12:05 pm - 1:05 pmRDU-MDW
2h 00mnonstop
Southwest Logo
8:20 pm - 11:10 pmMDW-RDU
1h 50mnonstop
$177Southwest
Find Deal
Thu, Oct 2 - Sun, Oct 5
Delta Logo
5:20 am - 9:48 amRDU-MDW
5h 28m1 stop
Delta Logo
4:25 pm - 9:35 pmMDW-RDU
4h 10m1 stop
$197Delta
Find Deal
Sat, Oct 4 - Sat, Oct 4

Southwest flights from Raleigh to Chicago Midway Airport

Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Southwest
Nov 1
RDU6:35 amRaleigh-Durham
1h 55m
MDW7:30 amChicago Midway
Nov 11
MDW6:05 pmChicago Midway
1h 50m
RDU8:55 pmRaleigh-Durham
$139
Find similar
Southwest
Sep 23
RDU1:35 pmRaleigh-Durham
1h 55m
MDW2:30 pmChicago Midway
Sep 26
MDW1:50 pmChicago Midway
1h 55m
RDU4:45 pmRaleigh-Durham
$158
Find similar
Southwest
Oct 2
RDU12:05 pmRaleigh-Durham
2h 00m
MDW1:05 pmChicago Midway
Oct 5
MDW8:20 pmChicago Midway
1h 50m
RDU11:10 pmRaleigh-Durham
$177
Find similar

Delta flights from Raleigh to Chicago Midway Airport

Our best Delta deals on Raleigh to Chicago Midway Airport flight tickets
Delta
Oct 4
RDU5:20 amRaleigh-Durham
5h 28m
1 stop
MDW9:48 amChicago Midway
Oct 4
MDW4:25 pmChicago Midway
4h 10m
1 stop
RDU9:35 pmRaleigh-Durham
$197
Find similar
Delta
Sep 1
RDU7:45 amRaleigh-Durham
6h 51m
1 stop
MDW1:36 pmChicago Midway
Sep 2
MDW6:17 pmChicago Midway
3h 59m
1 stop
RDU11:16 pmRaleigh-Durham
$258
Find similar
Delta
Aug 30
RDU5:15 pmRaleigh-Durham
4h 57m
1 stop
MDW9:12 pmChicago Midway
Sep 2
MDW6:17 pmChicago Midway
3h 59m
1 stop
RDU11:16 pmRaleigh-Durham
$278
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 August 18, 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

Sat 11/1

6:35 am-7:30 am

Nonstop1h 55m

Chicago Midway

Tue 11/11

6:05 pm-8:55 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 10/17

7:15 pm-11:25 pm

1 stop5h 10m

Chicago Midway

Mon 10/20

6:20 am-6:20 pm

1 stop11h 00m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 10/20

8:49 am-5:27 pm

1 stop9h 38m

Chicago Midway

Thu 10/23

8:25 am-1:41 pm

1 stop4h 16m

$144

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

6:05 pm-11:44 am

1 stop18h 39m

Chicago Midway

Sat 10/18

6:15 am-6:50 pm

1 stop11h 35m

$148

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 10/10

6:42 pm-4:09 pm

1 stop22h 27m

Chicago Midway

Tue 10/14

8:05 am-3:37 pm

1 stop6h 32m

$149

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 9/12

6:22 am-4:00 pm

1 stop10h 38m

Chicago Midway

Mon 9/15

8:15 am-1:38 pm

1 stop4h 23m

$153

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 9/6

6:06 pm-12:44 pm

1 stop19h 38m

Chicago Midway

Sat 9/13

10:51 am-9:53 am

1 stop22h 02m

$154

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 9/23

1:35 pm-2:30 pm

Nonstop1h 55m

Chicago Midway

Fri 9/26

1:50 pm-4:45 pm

Nonstop1h 55m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/2

12:05 pm-1:05 pm

Nonstop2h 00m

Chicago Midway

Sun 10/5

8:20 pm-11:10 pm

Nonstop1h 50m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/4

5:20 am-9:48 am

1 stop5h 28m

Chicago Midway

Sat 10/4

4:25 pm-9:35 pm

1 stop4h 10m

$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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Raleigh, with most prices found around $224. If you are unable to visit Chicago Midway Airport during the month of September, 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 $336. 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 $402.

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 in the morning because they tend to be around $371. 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 $292 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 $177 on momondo.

What cabin class options are available on Raleigh-Durham to Chicago Midway flights?

There are 1 cabin classes 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.

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

$84

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 $84. The best round-trip flight deal from Raleigh to Chicago Midway Airport found on momondo in the last 72 hours is $139.
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 $106Free CancellationRating
5.8
3,212 reviews
Search Frontier flights
DeltaPriceFrom $157Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $178Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $197Free CancellationRating
7.4
8,925 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 $314, but momondo users have found Southwest deals from Raleigh to Chicago Midway Airport from as low as $178 round-trip. Southwest has been scored 8.0/10 in 4,246 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.

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