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$80+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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Cheapflights Tip: The best prices from Durham to Chicago are usually found in August or July, booked 85 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 July 1, 2025.

Round-trip from

$161
(Kiwi.com)

One-way from

$80
(FlightHub)

Popular in

March

Cheapest in

August

Average price

$198
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. 20% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/1. 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 7/194:44 pmRDU - ORD
1 stop7h 45mFrontier
Mon 8/1111:15 amORD - RDU
Nonstop2h 13mFrontier
Deal found 7/1$161
This Priceline deal was found by Cheapflights users on 7/1. 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.
Fri 7/115:07 pmRDU - MDW
1 stop7h 10mFrontier
Mon 7/146:20 amMDW - RDU
1 stop8h 52mFrontier
Deal found 7/1$164
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:24 amRDU - ORD
Nonstop2h 20mAmerican Airlines
Thu 8/218:19 amORD - RDU
Nonstop2h 12mAmerican Airlines
Deal found 6/30$177
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 8/156:30 pmRDU - MDW
Nonstop2h 00mSouthwest
Mon 8/186:25 pmMDW - RDU
Nonstop1h 55mSouthwest
Deal found 6/29$177
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/139:49 amRDU - ORD
1 stop3h 56mDelta
Fri 8/155:45 amORD - RDU
1 stop4h 30mDelta
Deal found 6/30$197
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/78:50 amRDU - MDW
1 stop3h 58mDelta
Mon 8/116:17 pmMDW - RDU
1 stop3h 59mDelta
Deal found 6/30$197
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:20 pmRDU - ORD
1 stop4h 58mMultiple Airlines
Sun 10/2611:32 amORD - RDU
Nonstop2h 06mMultiple Airlines
Deal found 6/30$209
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Fri 10/1012:20 pmRDU - RFD
1 stop7h 38mMultiple Airlines
Mon 10/133:07 pmRFD - RDU
2 stops17h 29mMultiple Airlines
Deal found 7/1$461

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 July 1, 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 7/19

4:44 pm-11:29 pm

1 stop7h 45m

Chicago O'Hare Intl

Mon 8/11

11:15 am-2:28 pm

Nonstop2h 13m

$161

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 7/11

5:07 pm-11:17 pm

1 stop7h 10m

Chicago Midway

Mon 7/14

6:20 am-4:12 pm

1 stop8h 52m

$164

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 8/12

7:24 am-8:44 am

Nonstop2h 20m

Chicago O'Hare Intl

Thu 8/21

8:19 am-11:31 am

Nonstop2h 12m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 8/15

6:30 pm-7:30 pm

Nonstop2h 00m

Chicago Midway

Mon 8/18

6:25 pm-9:20 pm

Nonstop1h 55m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 8/13

9:49 am-12:45 pm

1 stop3h 56m

Chicago O'Hare Intl

Fri 8/15

5:45 am-11:15 am

1 stop4h 30m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 8/7

7:30 am-11:48 am

1 stop5h 18m

Chicago Midway

Mon 8/11

6:42 pm-12:15 am

1 stop4h 33m

$197

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Fri 10/10

12:20 pm-6:58 pm

1 stop7h 38m

Chicago Greater Rockford

Mon 10/13

3:07 pm-9:36 am

2 stops17h 29m

$461

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 9/4

6:33 pm-12:10 am

1 stop6h 37m

$80

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 10/19

3:46 pm-9:08 pm

1 stop6h 22m

$80

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 7/19

8:38 pm-8:55 am

1 stop13h 17m

$83

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 19 results
1
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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 June 27, 2025.

To ensure you get the cheapest price possible for a flight from Durham to Chicago, you should look to book at least 32 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 July 1, 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.

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 July 1, 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
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Sun Country Air
6.9
Okay
340 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $80. Spirit Airlines flights start at $83 while deals on United Airlines 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: SkyWest Airlines (100%), SWISS (94%), Japan Airlines( 93%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $1,852, our data shows the cheapest flight currently is $97. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $134 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 Durham?

Book flights to Durham if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$43Average$162FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$98Average$263FlexibilityNo cancel feeOn-time65%
DeltaCheapest$102Average$319FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$145Average$338FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$359FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$170Average$314FlexibilityNo cancel feeOn-time63%

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