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$84+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Durham to Chicago are usually found in August or September, booked 82 days in advance, depart on a Thursday or Friday and return on a Thursday

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 agosto 14, 2025.

Round-trip from

$143
(CheapOair)

One-way from

$84
(CheapOair)

Popular in

March

Cheapest in

August

Average price

$211
From Durham to Chicago (CHI)
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One-way flight from Durham to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 14, 2025.

This CheapOair deal was found by Cheapflights users on 8/14. 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.
mié. 9/106:45 amRDU - ORD
1 stop11h 54mFrontier
sáb. 9/1312:22 pmORD - RDU
1 stop9h 25mFrontier
Deal found 8/14$143
This Mytrip deal was found by Cheapflights users on 8/14. 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.
vie. 9/266:42 pmRDU - MDW
1 stop5h 38mFrontier
mié. 10/19:00 amMDW - RDU
1 stop10h 37mFrontier
Deal found 8/14$143
This Frontier deal was found by Cheapflights users on 8/12. 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.
sáb. 10/252:36 pmRDU - ORD
1 stop7h 12mFrontier
jue. 10/3012:32 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 8/12$144
This Frontier deal was found by Cheapflights users on 8/12. 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.
lun. 9/83:35 pmRDU - ORD
Nonstop2h 16mFrontier
jue. 9/1111:36 amORD - RDU
Nonstop2h 14mFrontier
Deal found 8/12$146
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
sáb. 9/202:33 pmRDU - ORD
1 stop8h 38mMultiple Airlines
lun. 9/2211:36 amORD - RDU
Nonstop2h 14mMultiple Airlines
Deal found 8/11$147
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/73:35 pmRDU - ORD
Nonstop2h 16mFrontier
jue. 9/1111:36 amORD - RDU
Nonstop2h 14mFrontier
Deal found 8/13$148
This CheapOair deal was found by Cheapflights users on 8/14. 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.
jue. 9/46:38 pmRDU - MDW
1 stop5h 42mFrontier
dom. 9/76:21 amMDW - RDU
1 stop9h 50mFrontier
Deal found 8/14$148
This CheapOair deal was found by Cheapflights users on 8/14. 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.
mar. 9/236:45 amRDU - ORD
1 stop11h 54mFrontier
dom. 9/288:49 pmORD - RDU
1 stop12h 04mFrontier
Deal found 8/14$149
This CheapOair deal was found by Cheapflights users on 8/14. 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.
vie. 10/106:42 pmRDU - MDW
1 stop22h 27mFrontier
mar. 10/148:05 amMDW - RDU
1 stop6h 32mFrontier
Deal found 8/14$149
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
jue. 9/183:35 pmRDU - ORD
Nonstop2h 16mFrontier
dom. 9/2111:36 amORD - RDU
Nonstop2h 14mFrontier
Deal found 8/11$150
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
lun. 8/256:10 amRDU - ORD
1 stop5h 29mFrontier
jue. 8/286:35 amORD - RDU
1 stop6h 16mFrontier
Deal found 8/13$151
This Frontier deal was found by Cheapflights users on 8/12. 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.
jue. 12/112:45 pmRDU - ORD
Nonstop2h 28mFrontier
dom. 12/144:16 pmORD - RDU
Nonstop2h 05mFrontier
Deal found 8/12$152

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 agosto 14, 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

mié. 9/10

6:45 am-5:39 pm

1 stop11h 54m

Chicago O'Hare Intl

sáb. 9/13

12:22 pm-10:47 pm

1 stop9h 25m

$143

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

jue. 10/16

7:15 pm-12:11 am

1 stop5h 56m

Chicago O'Hare Intl

lun. 10/20

12:28 pm-10:59 pm

1 stop9h 31m

$143

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

lun. 9/8

3:35 pm-4:51 pm

Nonstop2h 16m

Chicago O'Hare Intl

jue. 9/11

11:36 am-2:50 pm

Nonstop2h 14m

$143

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

jue. 9/4

6:38 pm-12:10 am

1 stop6h 32m

Chicago O'Hare Intl

vie. 9/5

5:10 am-5:38 pm

1 stop11h 28m

$143

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

jue. 11/6

6:10 am-10:41 am

1 stop5h 31m

Chicago O'Hare Intl

lun. 11/10

11:24 am-10:58 pm

1 stop10h 34m

$143

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

vie. 9/19

6:42 pm-12:10 am

1 stop6h 28m

Chicago O'Hare Intl

lun. 9/22

5:10 am-5:38 pm

1 stop11h 28m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

mié. 9/10

6:45 am-3:58 pm

1 stop10h 13m

Chicago Midway

vie. 9/12

5:15 pm-10:58 pm

1 stop4h 43m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

mar. 9/16

6:45 am-3:58 pm

1 stop10h 13m

Chicago Midway

mié. 9/17

9:00 am-8:37 pm

1 stop10h 37m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

vie. 9/26

6:42 pm-11:20 pm

1 stop5h 38m

Chicago Midway

mié. 10/1

9:00 am-8:37 pm

1 stop10h 37m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

vie. 10/17

7:15 pm-11:25 pm

1 stop5h 10m

Chicago Midway

lun. 10/20

6:20 am-6:20 pm

1 stop11h 00m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 57 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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Durham to Chicago, you should look to book at least 82 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, August is the cheapest month in which you can book a flight from Durham to Chicago (average of $245). Flying from Durham to Chicago in March is currently the most expensive (average of $321). 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 agosto 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Durham to Chicago as you normally would.

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 Thursday 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 agosto 14, 2025.

The most flights from DU8 to CHI are scheduled on a Thursday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 agosto 14, 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
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,219 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $84. American Airlines flights start at $85 while deals on Southwest start at $85 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: SkyWest Airlines (100%), SWISS (90%), Japan Airlines( 87%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $809, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $131 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, August is the cheapest month in which you can book a flight from Durham to Chicago (average of $245). Flying from Durham to Chicago in March is currently the most expensive (average of $321). 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?

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Lansing
Hammond
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Porter
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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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$188FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$98Average$279FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$305FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$154Average$360FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$348FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$170Average$312FlexibilityNo cancel feeOn-time63%

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