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$118+ Cheap flights from Raleigh (RDU) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
1 adult, Economy
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Cheapflights Tip: The best prices from Raleigh-Durham to Chicago are usually found in December or October, booked 76 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap flight deals from Raleigh to Chicago

Cheapest flights from Raleigh to Chicago
Explore the most affordable flight options available from Raleigh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
RDU
-
ORD
1 stop15h 03m
Frontier
Sat 8/222:41 pm
ORD
-
RDU
2 stops32h 18m
Frontier
Deal found 7/30$241
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:59 pm
RDU
-
MDW
1 stop6h 01m
Delta
Tue 11/311:39 am
MDW
-
RDU
1 stop4h 26m
Delta
Deal found 7/31$241
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:46 pm
RDU
-
RFD
1 stop13h 08m
Multiple Airlines
Wed 11/43:34 pm
RFD
-
RDU
1 stop16h 26m
Multiple Airlines
Deal found 7/30$241
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
RDU
-
ORD
1 stop15h 03m
Multiple Airlines
Thu 8/277:05 am
ORD
-
RDU
2 stops14h 23m
Multiple Airlines
Deal found 7/31$242
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 pm
RDU
-
MDW
1 stop7h 45m
Southwest
Tue 9/812:45 pm
MDW
-
RDU
2 stops5h 05m
Southwest
Deal found 7/31$242
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:05 am
RDU
-
ORD
1 stop14h 54m
Multiple Airlines
Tue 9/12:41 pm
ORD
-
RDU
2 stops17h 17m
Multiple Airlines
Deal found 7/30$243
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:50 pm
RDU
-
MDW
2 stops7h 30m
Southwest
Sat 8/227:40 am
MDW
-
RDU
2 stops10h 15m
Southwest
Deal found 7/29$243
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:06 pm
RDU
-
ORD
2 stops36h 56m
Frontier
Tue 8/188:05 am
ORD
-
RDU
1 stop12h 10m
Frontier
Deal found 7/28$244
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
RDU
-
MDW
2 stops15h 26m
Frontier
Sat 8/2211:45 am
MDW
-
RDU
1 stop11h 14m
Frontier
Deal found 7/30$244
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am
RDU
-
ORD
Nonstop2h 31m
American Airlines
Mon 9/216:29 am
ORD
-
RDU
1 stop3h 47m
American Airlines
Deal found 7/31$245
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:20 pm
RDU
-
MDW
1 stop4h 50m
Southwest
Mon 9/216:30 pm
MDW
-
RDU
Nonstop2h 00m
Southwest
Deal found 7/31$245
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
RDU
-
MDW
1 stop5h 50m
Frontier
Thu 8/2711:50 am
MDW
-
RDU
1 stop11h 09m
Frontier
Deal found 7/31$246

Find flight deals from Raleigh to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Raleigh (RDU) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Kiwi.com)

One-way from

$118
(United Airlines)

Popular in

July

Cheapest in

December

Average price

$289

Good round-trip deal

$340 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for Raleigh-Durham-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Raleigh-Durham-Chicago (CHI) flights.
Search Deals
From Raleigh-Durham to Chicago (CHI)
Search Deals
One-way flight from Raleigh-Durham to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Raleigh-Durham to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Raleigh-Durham to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Raleigh to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated August 2, 2026.
Use the filters below to find and compare flights from Raleigh to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 9/14

4:20 pm-8:10 pm

1 stop4h 50m

Chicago Midway

Mon 9/21

6:30 pm-9:30 pm

Nonstop2h 00m

$245
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 8/28

6:45 pm-7:40 pm

Nonstop1h 55m

Chicago Midway

Tue 9/8

8:35 am-11:35 am

Nonstop2h 00m

$249

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 8/21

6:45 pm-7:40 pm

Nonstop1h 55m

Chicago Midway

Mon 8/24

8:50 am-11:50 am

Nonstop2h 00m

$249

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 9/4

6:55 pm-10:00 pm

1 stop4h 05m

Chicago Midway

Sun 9/6

8:55 am-11:55 am

Nonstop2h 00m

$259

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Tue 10/6

5:27 pm-8:44 am

1 stop16h 17m

Chicago Greater Rockford

Fri 10/9

8:02 pm-8:59 am

1 stop11h 57m

$265

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 9/9

1:45 pm-7:05 pm

2 stops6h 20m

Chicago Midway

Wed 9/16

2:00 pm-9:25 pm

2 stops6h 25m

$265

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 9/14

4:50 pm-11:25 pm

2 stops7h 35m

Chicago Midway

Tue 9/15

10:30 am-7:05 pm

2 stops7h 35m

$265

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Thu 9/10

9:35 pm-8:52 am

1 stop12h 17m

Chicago Greater Rockford

Mon 9/14

5:20 pm-9:59 am

1 stop15h 39m

$271

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 9/8

10:10 am-11:34 am

Nonstop2h 24m

Chicago O'Hare Intl

Thu 9/10

12:50 pm-4:02 pm

Nonstop2h 12m

$277

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 10/1

8:06 am-9:30 am

Nonstop2h 24m

Chicago O'Hare Intl

Sun 10/4

9:05 am-12:28 pm

Nonstop2h 23m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 52 resultsSorted by cheapest first
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Compare providers for flights from Raleigh to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Raleigh to Chicago in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
WAYAPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Raleigh-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Raleigh-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Raleigh-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Raleigh-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Raleigh-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Raleigh to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Raleigh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Raleigh to Chicago

What is the cheapest month to book a flight from Raleigh to Chicago?

Currently, October is the cheapest month in which you can book a flight from Raleigh to Chicago (average of $228). Flying from Raleigh to Chicago in July is currently the most expensive (average of $375). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RDU to CHI?

Find hourly flight availability from Raleigh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2026.

One of the essential ways to save on airfare from Raleigh to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 24% on airfare.

Weekly flight availability from Raleigh to Chicago

Explore weekly flight availability from Raleigh to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 2, 2026.

The most flights from RDU to CHI are scheduled on a Friday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Raleigh to Chicago?

Airfare is typical for this route at the moment.
Raleigh to Chicago flights typically cost between $205 and $336 in August.
The cheapest round-trip price found within the last 5 days was $241 on Frontier (Aug 19-Aug 22).

How often are flights from Raleigh to Chicago delayed?

About 11% of weekly flights between Raleigh and Chicago have experienced delays in the past year, with the average delay time being 151 minutes.

What is the most punctual flight time for Raleigh to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Raleigh to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Raleigh to Chicago?

Booking 65 days in advance of your planned departure date is, on average, the best time to get cheap flights from Raleigh to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Raleigh to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Raleigh to Chicago. Price data was last updated on August 1, 2026.

Travelers seeking maximum savings on their Raleigh to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Raleigh to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Raleigh to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
John Walton

John Walton

Expert on RDU

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 2, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Raleigh to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,230 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,230 reviews
Southwest
8.0
Very good
4,230 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,061 reviews
Southwest
8.0
Very good
4,230 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,846 reviews
Southwest
8.0
Very good
4,230 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,033 reviews
Southwest
8.0
Very good
4,230 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,741 reviews
Southwest
8.0
Very good
4,230 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Raleigh to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Raleigh to Chicago?

    Raleigh-Durham (RDU) is the airport you will fly out of if you book a flight from Raleigh to Chicago. You should not have trouble finding flights to Chicago from Raleigh-Durham; the airport handles an average of 19 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 6 airlines have flights from the Raleigh airport to Chicago. It is only a 11.1 mi journey to Raleigh-Durham (RDU) from Raleigh’s city center.

  • How long is the flight from Raleigh to Chicago?

    A quick flight from Raleigh to Chicago can take about 2h 24m. Southwest provides one of the quickest options available for as low as $277. Raleigh and Chicago are separated by a distance of 645 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Raleigh to Chicago round-trip?

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $72. Additional round-trip tickets that might be worth considering are offered by Delta and JetBlue, with the lowest prices starting at $88 and $160, respectively. Users have found that Frontier is 75% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Raleigh to Chicago one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $52. However, be on the lookout for offers from United Airlines and Southwest, as they are both options that can get you from Raleigh to Chicago for a low price.

  • What are the most popular routes from Raleigh to Chicago?

    The most popular flight routes from Raleigh to Chicago are Raleigh-Durham - Chicago O'Hare Intl, Raleigh-Durham - Chicago Midway and Raleigh-Durham - Chicago Greater Rockford.

  • What are the most reliable airlines from Raleigh to Chicago?

    Consider Frontier (100%), Volaris (100%) or SWISS (91%) when booking your flight. These represent the most reliable airlines when flying from Raleigh to Chicago.

  • What are the cheapest flights from Raleigh to Chicago?

    Looking for the cheapest flight from Raleigh to Chicago? While on average our users pay $1,965, our data indicates the cheapest price to be $118. The most popular route (Raleigh-Durham - Chicago O'Hare Intl), is priced around $163.

  • Can I find deals for flights from Raleigh to Chicago that include hotel bookings?

    Yes. In addition to deals on Raleigh to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Raleigh to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Raleigh to Chicago.

  • Can I find deals for business class flights from Raleigh to Chicago?

    Yes. Cheapflights offers flight deals from Raleigh to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Raleigh to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Raleigh to Chicago (average of $228). Flying from Raleigh to Chicago in July is currently the most expensive (average of $375). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 6 airlines flying from Raleigh to Chicago

Discover the top 6 airlines that operate flights from Raleigh to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$192FlexibilityNo cancel feeOn-time62%
DeltaCheapest$88Average$332FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$160Average$330FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$168Average$331FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$319FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$188Average$339FlexibilityNo cancel feeOn-time63%

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