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$61+ Cheap flights from Durham, NC 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheapflights Tip: The best prices from 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 Durham to Chicago

Cheapest flights from Durham to Chicago
Explore the most affordable flight options available from Durham to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/244:05 pmRDU - ORD
Nonstop2h 25mMultiple Airlines
Thu 11/278:45 amORD - RDU
1 stop9h 59mMultiple Airlines
Deal found 11/3$125
This Priceline deal was found by Cheapflights users on 11/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:10 amRDU - ORD
1 stop6h 04mFrontier
Sun 11/235:30 amORD - RDU
1 stop7h 35mFrontier
Deal found 11/3$127
This Frontier deal was found by Cheapflights users on 11/4. 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.
Thu 11/209:11 amRDU - MDW
1 stop11h 20mFrontier
Sun 11/236:05 amMDW - RDU
1 stop11h 14mFrontier
Deal found 11/4$127
This CheapOair deal was found by Cheapflights users on 11/3. 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.
Fri 12/1210:09 amRDU - ORD
1 stop12h 58mFrontier
Tue 12/164:22 pmORD - RDU
1 stop6h 50mFrontier
Deal found 11/3$128
This CheapOair deal was found by Cheapflights users on 11/3. 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 12/412:53 pmRDU - MDW
1 stop6h 15mFrontier
Fri 12/53:52 pmMDW - RDU
1 stop23h 52mFrontier
Deal found 11/3$128
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/244:05 pmRDU - ORD
Nonstop2h 25mFrontier
Tue 12/24:22 pmORD - RDU
2 stops25h 57mFrontier
Deal found 11/3$129
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/43:21 pmRDU - MDW
1 stop7h 32mFrontier
Thu 12/117:23 pmMDW - RDU
1 stop13h 53mFrontier
Deal found 11/3$129
This Booking.com deal was found by Cheapflights users on 11/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:14 pmRDU - ORD
1 stop18h 17mFrontier
Tue 12/164:22 pmORD - RDU
1 stop6h 50mFrontier
Deal found 11/3$130
This Frontier deal was found by Cheapflights users on 11/2. 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.
Tue 12/235:24 pmRDU - ORD
Nonstop2h 28mFrontier
Tue 12/301:14 pmORD - RDU
Nonstop2h 05mFrontier
Deal found 11/2$131
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/176:10 amRDU - ORD
1 stop5h 31mFrontier
Tue 11/186:40 amORD - RDU
1 stop11h 38mFrontier
Deal found 11/3$133
This Priceline deal was found by Cheapflights users on 11/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/207:15 pmRDU - ORD
1 stop5h 53mFrontier
Sun 11/2312:17 pmORD - RDU
Nonstop2h 03mFrontier
Deal found 11/2$134
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/244:05 pmRDU - ORD
Nonstop2h 25mMultiple Airlines
Mon 12/16:15 pmORD - RDU
1 stop14h 32mMultiple Airlines
Deal found 11/3$136

Cheap flight deals from Durham to Chicago

Keep the following information in mind while searching for Durham to Chicago flight deals. Data was last updated November 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$125
(Kiwi.com)

One-way from

$61
(CheapOair)

Popular in

March

Cheapest in

August

Average price

$256
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 Durham to Chicago (CHI)
Search Deals
One-way flight from Durham to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($60 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 November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Durham 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 November 4, 2025.
Use the filters below to find and compare flights from Durham to Chicago that are best for you.

Fly from

Durham

Fly to

Chicago

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 12/6

10:00 am-11:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Sat 12/13

6:37 pm-9:46 pm

Nonstop2h 09m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Wed 12/17

1:45 pm-4:30 pm

Nonstop1h 45m

$139

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 - 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

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Mon 12/8

6:05 pm-8:55 pm

Nonstop1h 50m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

7:15 am-12:34 pm

1 stop6h 19m

Chicago Midway

Sat 12/13

6:00 am-11:34 am

1 stop4h 34m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 12/5

5:26 pm-6:55 pm

Nonstop2h 29m

Chicago O'Hare Intl

Mon 12/8

11:04 am-2:07 pm

Nonstop2h 03m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 11/24

8:15 am-11:52 am

1 stop4h 37m

Chicago Midway

Thu 11/27

6:00 am-11:38 am

1 stop4h 38m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 12/15

6:20 am-7:46 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 1/6

11:00 am-2:02 pm

Nonstop2h 02m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 12/4

5:26 pm-6:55 pm

Nonstop2h 29m

Chicago O'Hare Intl

Fri 12/12

6:12 pm-9:21 pm

Nonstop2h 09m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 53 results
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Best time to book a flight from Durham to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Durham 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 Durham to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Durham to Chicago. Price data was last updated on October 31, 2025.

To ensure you get the cheapest price possible for a flight from Durham to Chicago, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, October is the cheapest month in which you can book a flight from Durham to Chicago (average of $83). Flying from Durham 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 DU8 to CHI?

Find hourly flight availability from Durham 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 November 4, 2025.

One of the essential ways to save on airfare from Durham to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 26% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Durham to Chicago. Price data was last updated on December 16, 2024.

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

Weekly flight availability from Durham to Chicago

Explore weekly flight availability from Durham 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 November 4, 2025.

The most flights from DU8 to CHI are scheduled on a Monday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

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 November 4, 2025.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
8,003 reviews
Southwest
8.0
Very good
4,239 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
9,002 reviews
Southwest
8.0
Very good
4,239 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
11,040 reviews
Southwest
8.0
Very good
4,239 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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
3,117 reviews
Southwest
8.0
Very good
4,239 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

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 Durham to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Durham to Chicago?

    There are many flights that can get you from Durham to Chicago in 2h 05m. Fly via United Airlines, Southwest, or Delta to get the fastest option. The distance from Durham to Chicago is about 631 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $70. Southwest flights start at $70 while deals on Delta start at $89 one-way.

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

    The most popular flight routes from Durham 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 Durham to Chicago?

    Before booking your flight to Chicago from Durham, check out the most reliable airlines to get you to your destination on time: Emirates (96%), Cathay Pacific (90%), ANA( 87%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $856, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $108 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Durham 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 Durham to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Durham to Chicago (average of $83). Flying from Durham 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 Durham 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 Durham to Chicago

Discover the top 6 airlines that operate flights from Durham 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$79Average$188FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$324FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$114Average$279FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$168Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$172Average$349FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$317FlexibilityNo cancel feeOn-time63%

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