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$101+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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Cheapflights Tip: The best prices from Durham to Chicago are usually found in December or October, booked 82 days in advance, depart on a Thursday or Friday and return on a Thursday

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 April 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:15 pm
RDU
-
ORD
1 stop25h 58m
Multiple Airlines
Mon 6/17:33 pm
ORD
-
RDU
2 stops15h 26m
Multiple Airlines
Deal found 4/12$187
This Super.com deal was found by Cheapflights users on 4/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:03 pm
RDU
-
ORD
Nonstop2h 19m
Frontier
Sat 4/254:28 pm
ORD
-
RDU
1 stop5h 27m
Frontier
Deal found 4/13$188
This Expedia deal was found by Cheapflights users on 4/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
RDU
-
ORD
1 stop12h 00m
Frontier
Fri 4/242:09 pm
ORD
-
RDU
Nonstop2h 07m
Frontier
Deal found 4/12$190
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:54 pm
RDU
-
MDW
1 stop23h 15m
Frontier
Sun 5/3112:27 pm
MDW
-
RDU
1 stop10h 57m
Frontier
Deal found 4/12$190
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Fri 5/292:52 pm
RDU
-
ORD
1 stop9h 21m
Frontier
Fri 6/58:05 am
ORD
-
RDU
1 stop29h 07m
Frontier
Deal found 4/14$191
This CheapOair deal was found by Cheapflights users on 4/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Mon 5/184:52 pm
MDW
-
RDU
1 stop15h 29m
Frontier
Deal found 4/13$191
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Tue 4/286:00 am
RDU
-
ORD
1 stop5h 02m
Multiple Airlines
Sat 5/27:15 pm
ORD
-
RDU
2 stops36h 31m
Multiple Airlines
Deal found 4/13$192
This Super.com deal was found by Cheapflights users on 4/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:33 pm
RDU
-
MDW
1 stop10h 29m
Frontier
Mon 5/184:52 pm
MDW
-
RDU
1 stop15h 29m
Frontier
Deal found 4/13$192
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:16 am
RDU
-
ORD
1 stop13h 45m
Frontier
Tue 6/91:50 pm
ORD
-
RDU
1 stop9h 39m
Frontier
Deal found 4/12$193
This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:00 pm
RDU
-
MDW
1 stop7h 14m
Frontier
Thu 4/302:15 pm
MDW
-
RDU
1 stop8h 05m
Frontier
Deal found 4/14$193
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
RDU
-
ORD
1 stop5h 02m
Frontier
Fri 5/12:09 pm
ORD
-
RDU
Nonstop2h 07m
Frontier
Deal found 4/14$194
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:52 pm
RDU
-
MDW
2 stops26h 10m
Frontier
Mon 5/1812:04 pm
MDW
-
RDU
1 stop23h 00m
Frontier
Deal found 4/12$194

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 April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$187
(Kiwi.com)

One-way from

$101
(Super.com)

Popular in

February

Cheapest in

December

Average price

$276
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. 14% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 17, 2026.
Use the filters below to find and compare flights from Durham to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Thu 5/28

3:20 pm-7:45 am

1 stop17h 25m

Chicago Greater Rockford

Sun 5/31

11:27 am-10:52 am

1 stop22h 25m

$224

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Tue 5/19

8:01 pm-9:21 am

1 stop14h 20m

Chicago Greater Rockford

Thu 5/21

11:27 am-10:52 am

1 stop22h 25m

$230

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 5/15

6:20 am-7:48 am

Nonstop2h 28m

Chicago O'Hare Intl

Mon 5/18

9:35 pm-12:50 am

Nonstop2h 15m

$237

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 5/12

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Tue 5/19

3:00 pm-9:35 pm

1 stop5h 35m

$247

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 5/5

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Wed 5/6

9:20 am-6:05 pm

1 stop7h 45m

$247
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 5/5

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Sat 5/9

3:45 pm-6:35 pm

Nonstop1h 50m

$251

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 6/27

5:33 am-10:35 am

1 stop6h 02m

Chicago O'Hare Intl

Tue 6/30

6:40 am-2:29 pm

1 stop6h 49m

$252

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 9/5

1:50 pm-8:17 pm

1 stop7h 27m

Chicago O'Hare Intl

Mon 9/7

5:30 am-12:50 pm

1 stop6h 20m

$252

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 5/26

5:40 am-10:29 am

1 stop5h 49m

Chicago O'Hare Intl

Tue 5/26

6:06 pm-12:16 am

1 stop5h 10m

$257

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 5/28

5:40 am-8:45 am

1 stop4h 05m

Chicago O'Hare Intl

Thu 5/28

2:59 pm-9:53 pm

1 stop5h 54m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 59 resultsSorted by cheapest first
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6

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 April 10, 2026.

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 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 April 17, 2026.

One of the essential ways to save on airfare from Durham 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 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 April 11, 2026.

Travelers seeking maximum savings on their Durham to Chicago flight should consider departing on Friday 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 April 17, 2026.

The most flights from DU8 to CHI are scheduled on a Friday (40 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 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 April 17, 2026.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,602 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,939 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,593 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,986 reviews
Southwest
8.0
Very good
4,328 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. 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 Frontier, which is currently one of the cheapest options available, starting at $54. American Airlines flights start at $74 while deals on United Airlines start at $84 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: SWISS (85%), ANA (84%), Envoy Air( 83%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $711, our data shows the cheapest flight currently is $118. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $124 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.

See more FAQs

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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 April 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$75Average$191FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$287FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$147Average$312FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$160Average$293FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$170Average$343FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$304FlexibilityNo cancel feeOn-time63%

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