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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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheapflights Tip: The best prices from Durham to Chicago are usually found in August or October, booked 90 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap 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 December 12, 2025.

This Mytrip deal was found by Cheapflights users on 12/9. 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.
Tue 12/168:15 amRDU - ORD
1 stop7h 57mFrontier
Wed 12/174:01 pmORD - RDU
1 stop7h 11mFrontier
Deal found 12/9$162
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:05 pmRDU - ORD
1 stop10h 19mFrontier
Mon 1/512:39 pmORD - RDU
1 stop10h 34mFrontier
Deal found 12/11$163
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:05 pmRDU - MDW
1 stop10h 07mFrontier
Mon 1/56:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/11$163
This Expedia deal was found by Cheapflights users on 12/10. 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.
Tue 12/302:12 pmRDU - ORD
1 stop21h 06mFrontier
Sun 1/46:10 amORD - RDU
Nonstop2h 05mFrontier
Deal found 12/10$166
This Southwest deal was found by Cheapflights users on 12/9. 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 12/255:30 amRDU - MDW
Nonstop2h 00mSouthwest
Thu 12/256:05 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 12/9$177
This CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:15 amRDU - ORD
1 stop11h 31mFrontier
Tue 1/202:53 pmORD - RDU
1 stop7h 58mFrontier
Deal found 12/11$182
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Wed 12/311:05 pmRDU - ORD
1 stop10h 19mMultiple Airlines
Mon 1/512:09 pmORD - RDU
2 stops35h 03mMultiple Airlines
Deal found 12/11$184
This Frontier deal was found by Cheapflights users on 12/10. 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.
Wed 12/311:05 pmRDU - ORD
1 stop10h 19mFrontier
Thu 1/16:00 amORD - RDU
1 stop5h 00mFrontier
Deal found 12/10$188
This Expedia deal was found by Cheapflights users on 12/10. 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.
Thu 12/258:14 pmRDU - ORD
1 stop13h 38mFrontier
Sun 1/115:35 amORD - RDU
Nonstop2h 05mFrontier
Deal found 12/10$193
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/302:12 pmRDU - ORD
1 stop21h 06mFrontier
Thu 1/16:00 amORD - RDU
1 stop5h 00mFrontier
Deal found 12/10$194
This American Airlines deal was found by Cheapflights users on 12/9. 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.
Thu 12/256:00 amRDU - ORD
Nonstop2h 30mAmerican Airlines
Thu 12/251:38 pmORD - RDU
Nonstop2h 11mAmerican Airlines
Deal found 12/9$202
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:14 pmRDU - MDW
1 stop20h 51mFrontier
Thu 1/16:12 amMDW - RDU
1 stop4h 48mFrontier
Deal found 12/11$212

Find flight deals from Durham to Chicago

Keep the following information in mind while searching for Durham to Chicago flight deals. Data was last updated December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$113
(Frontier)

One-way from

$61
(Frontier)

Popular in

March

Cheapest in

August

Average price

$257
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. 19% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 12, 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

Sun 1/11

3:50 pm-8:18 am

1 stop17h 28m

Chicago O'Hare Intl

Tue 1/13

8:08 pm-10:43 pm

2 stops25h 35m

$146

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 1/9

10:00 am-5:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 1/12

6:45 am-1:44 pm

1 stop5h 59m

$161

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/25

8:15 am-11:25 am

1 stop4h 10m

Chicago Midway

Thu 12/25

6:05 pm-8:55 pm

Nonstop1h 50m

$187

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 12/16

8:15 am-3:12 pm

1 stop7h 57m

Chicago O'Hare Intl

Sun 12/21

6:10 am-9:15 am

Nonstop2h 05m

$224

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/14

5:15 am-10:27 am

1 stop6h 12m

Chicago Midway

Sun 1/18

6:45 am-11:52 am

1 stop4h 07m

$230

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/12

10:38 am-9:12 pm

1 stop11h 34m

Chicago Midway

Sun 2/15

6:00 am-3:45 pm

1 stop8h 45m

$233

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 1/1

8:29 am-9:55 am

Nonstop2h 26m

Chicago O'Hare Intl

Thu 1/8

8:52 am-2:06 pm

1 stop4h 14m

$235

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 1/10

7:30 am-1:15 pm

1 stop6h 45m

Chicago O'Hare Intl

Sat 1/17

11:00 am-2:03 pm

Nonstop2h 03m

$235

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 1/10

5:35 pm-6:40 pm

Nonstop2h 05m

Chicago Midway

Sat 1/17

2:40 pm-7:20 pm

1 stop3h 40m

$239

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 2/14

5:30 am-8:53 am

1 stop4h 23m

Chicago Midway

Mon 2/16

6:17 pm-11:40 pm

1 stop4h 23m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 December 5, 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, January is the cheapest month in which you can book a flight from Durham to Chicago (average of $61). Flying from Durham to Chicago in March is currently the most expensive (average of $198). 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 December 12, 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 15% 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 December 12, 2025.

The most flights from DU8 to CHI are scheduled on a Thursday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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

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 December 12, 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
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 4h 10m. Fly via JetBlue, Southwest, or Frontier 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 Frontier, which is currently one of the cheapest options available, starting at $54. Southwest flights start at $69 while deals on American Airlines start at $69 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: Cathay Pacific (87%), Royal Jordanian (86%), ANA( 84%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $814, 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 $121 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, January is the cheapest month in which you can book a flight from Durham to Chicago (average of $61). Flying from Durham to Chicago in March is currently the most expensive (average of $198). 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
Lansing
Merrillville
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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$187FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$81Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$306FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$162Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$173Average$350FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$314FlexibilityNo cancel feeOn-time63%

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