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$64+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Raleigh-Durham to Chicago are usually found in August or July, booked 90 days in advance, depart on a Thursday or Friday and return on a Thursday

Find 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 12/236:00 amRDU - ORD
1 stop17h 24mFrontier
Sat 1/106:11 pmORD - RDU
1 stop16h 47mFrontier
Deal found 10/28$128
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/236:00 amRDU - MDW
1 stop17h 12mFrontier
Tue 12/306:14 amMDW - RDU
1 stop16h 59mFrontier
Deal found 10/27$128
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/14:05 pmRDU - ORD
Nonstop2h 25mFrontier
Sat 12/61:24 pmORD - RDU
1 stop9h 48mFrontier
Deal found 10/29$129
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:10 amRDU - MDW
1 stop7h 31mFrontier
Fri 11/149:15 amMDW - RDU
1 stop5h 14mFrontier
Deal found 10/30$129
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:30 pmRDU - ORD
1 stop17h 43mFrontier
Mon 11/2412:17 pmORD - RDU
Nonstop2h 03mFrontier
Deal found 10/28$130
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:14 pmRDU - MDW
1 stop26h 44mFrontier
Mon 12/86:15 amMDW - RDU
1 stop4h 45mFrontier
Deal found 10/29$130
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1010:06 pmRDU - ORD
Nonstop2h 22mFrontier
Thu 11/131:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 10/28$131
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:06 pmRDU - ORD
Nonstop2h 22mFrontier
Sun 11/161:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 10/29$132
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:06 pmRDU - ORD
Nonstop2h 22mFrontier
Mon 11/171:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 10/28$135
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:58 pmRDU - ORD
Nonstop2h 25mFrontier
Sun 11/2312:17 pmORD - RDU
Nonstop2h 03mFrontier
Deal found 10/30$136
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:12 pmRDU - MDW
1 stop15h 00mFrontier
Mon 11/179:15 amMDW - RDU
1 stop5h 47mFrontier
Deal found 10/29$136
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 12/127:14 pmRDU - ORD
Nonstop2h 28mFrontier
Mon 12/156:30 pmORD - RDU
2 stops28h 42mFrontier
Deal found 10/27$137

Cheap 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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$128
(Kiwi.com)

One-way from

$64
(Priceline)

Popular in

March

Cheapest in

August

Average price

$229

Good round-trip deal

$227 or less

Good one-way deal

$98 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. 17% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 30, 2025.
Use the filters below to find and compare flights from Raleigh to Chicago that are best for you.

Fly from

Raleigh

Fly to

Chicago

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 11/13

7:05 pm-12:11 am

1 stop6h 06m

Chicago O'Hare Intl

Fri 11/14

7:34 pm-1:19 pm

1 stop16h 45m

$131

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Sat 12/13

9:50 am-12:45 pm

Nonstop1h 55m

$139

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 11/24

6:30 am-7:56 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 12/2

7:10 am-10:14 am

Nonstop2h 04m

$154

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:45 am-1:59 pm

1 stop9h 14m

Chicago Midway

Sat 12/13

6:00 am-4:44 pm

2 stops9h 44m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

1:09 pm-6:06 pm

1 stop5h 57m

Chicago Midway

Sat 12/13

1:14 pm-5:40 pm

1 stop3h 26m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 1/15

10:00 am-11:26 am

Nonstop2h 26m

Chicago O'Hare Intl

Thu 1/15

6:35 pm-9:46 pm

Nonstop2h 11m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/4

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Sun 12/7

7:30 pm-10:20 pm

Nonstop1h 50m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

6:00 pm-11:47 pm

1 stop6h 47m

Chicago Midway

Tue 12/16

10:49 am-4:47 pm

1 stop4h 58m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 1/10

6:15 am-7:44 am

Nonstop2h 29m

Chicago O'Hare Intl

Tue 1/13

2:02 pm-5:04 pm

Nonstop2h 02m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 12/12

5:26 pm-6:55 pm

Nonstop2h 29m

Chicago O'Hare Intl

Mon 12/15

2:05 pm-5:08 pm

Nonstop2h 03m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 50 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapfaremartPrice Accuracy-Trust 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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Raleigh-Chicago flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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

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

Use this chart to determine the optimal time to book a round-trip flight from Raleigh to Chicago. Price data was last updated on October 24, 2025.

Booking 90 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 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 $83). Flying from Raleigh to Chicago in March is currently the most expensive (average of $199). 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 October 30, 2025.

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 50% on airfare.

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 October 26, 2025.

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

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

The best insider tips for Raleigh to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Raleigh to Chicago trip
Airports
RDU

RDU's compact layout makes navigating its two terminals easy. Know your terminal in advance to streamline your departure process.

Read more about RDUby John Walton
ORD

At ORD, take the free shuttle train between terminals to navigate the sprawling airport layout efficiently.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line train for a quick, affordable ride to downtown Chicago from MDW, taking less than 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

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

John Walton

John Walton

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 October 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 14 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 05m. Southwest provides one of the quickest options available for as low as $139. Raleigh and Chicago are separated by a distance of 631 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 $79. Additional round-trip tickets that might be worth considering are offered by Delta and Spirit Airlines, with the lowest prices starting at $98 and $114, respectively. Users have found that Frontier is 72% 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 $68. 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 Emirates (92%), Cathay Pacific (89%) or ANA (88%) 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 $786, our data indicates the cheapest price to be $53. The most popular route (Raleigh-Durham - Chicago O'Hare Intl), is priced around $62.

  • 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 $83). Flying from Raleigh to Chicago in March is currently the most expensive (average of $199). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Raleigh to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$79Average$187FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$352FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$114Average$279FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$168Average$326FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$174Average$308FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$316FlexibilityNo cancel feeOn-time63%

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