HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Durham to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
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 May 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/188:52 pm
RDU
-
ORD
2 stops15h 48m
Frontier
Tue 5/191:59 pm
ORD
-
RDU
1 stop9h 34m
Frontier
Deal found 4/28$197
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/2112:54 pm
RDU
-
MDW
1 stop10h 08m
Frontier
Tue 5/266:00 am
MDW
-
RDU
1 stop4h 59m
Frontier
Deal found 4/28$198
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Fri 6/265:07 pm
RDU
-
ORD
1 stop7h 12m
Frontier
Wed 7/16:55 am
ORD
-
RDU
1 stop16h 26m
Frontier
Deal found 4/28$199
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:38 pm
RDU
-
ORD
1 stop8h 13m
Frontier
Tue 5/191:59 pm
ORD
-
RDU
1 stop17h 05m
Frontier
Deal found 4/29$200
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:15 pm
RDU
-
ORD
1 stop25h 58m
Frontier
Sun 5/1710:22 am
ORD
-
RDU
1 stop27h 05m
Frontier
Deal found 4/30$201
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:23 pm
RDU
-
MDW
1 stop10h 39m
Frontier
Tue 5/196:00 am
MDW
-
RDU
1 stop5h 04m
Frontier
Deal found 4/30$201
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/273:45 pm
RDU
-
ORD
2 stops17h 10m
Frontier
Sat 5/301:50 pm
ORD
-
RDU
1 stop9h 36m
Frontier
Deal found 4/30$202
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 8/811:47 am
RDU
-
MDW
1 stop11h 21m
Frontier
Tue 8/1112:11 pm
MDW
-
RDU
1 stop11h 14m
Frontier
Deal found 4/28$202
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:53 pm
RDU
-
ORD
Nonstop2h 46m
Frontier
Sun 5/178:39 am
ORD
-
RDU
Nonstop2h 19m
Frontier
Deal found 4/30$203
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:15 am
RDU
-
MDW
1 stop5h 49m
Frontier
Tue 8/1112:11 pm
MDW
-
RDU
1 stop11h 14m
Frontier
Deal found 4/29$203
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:47 am
RDU
-
ORD
1 stop9h 06m
Frontier
Tue 8/41:50 pm
ORD
-
RDU
1 stop9h 35m
Frontier
Deal found 4/29$204
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:15 am
RDU
-
MDW
1 stop5h 52m
Frontier
Sat 7/1812:11 pm
MDW
-
RDU
1 stop11h 14m
Frontier
Deal found 4/30$204

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 May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$197
(Kiwi.com)

One-way from

$101
(Cheapflightsfares)

Popular in

February

Cheapest in

December

Average price

$297
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. 13% potential increase in price ($43 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 May 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 May 3, 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

Sat 5/23

9:46 am-10:37 am

1 stop25h 51m

Chicago Greater Rockford

Sun 5/31

11:27 am-8:04 am

2 stops19h 37m

$213

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Wed 6/10

12:10 pm-10:37 am

2 stops23h 27m

Chicago Greater Rockford

Wed 6/17

4:42 pm-9:43 am

1 stop16h 01m

$232

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Tue 7/21

10:22 pm-9:13 am

1 stop11h 51m

Chicago Greater Rockford

Sun 7/26

11:27 am-8:06 am

2 stops19h 39m

$239

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Tue 6/16

10:22 pm-9:17 am

1 stop11h 55m

Chicago Greater Rockford

Wed 6/17

4:42 pm-9:43 am

1 stop16h 01m

$240

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/24

7:30 am-12:00 pm

1 stop5h 30m

Chicago Midway

Fri 7/3

11:05 am-4:11 pm

1 stop4h 06m

$257

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Thu 5/21

3:20 pm-7:45 am

1 stop17h 25m

Chicago Greater Rockford

Sun 5/24

11:27 am-12:24 am

2 stops11h 57m

$257

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Sun 5/17

10:15 pm-9:59 am

1 stop12h 44m

Chicago Greater Rockford

Mon 5/18

7:09 pm-9:59 am

1 stop13h 50m

$266

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 5/27

5:20 am-8:39 am

1 stop4h 19m

Chicago O'Hare Intl

Sat 5/30

5:30 am-11:52 am

1 stop5h 22m

$271

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 5/23

7:45 pm-11:26 pm

1 stop4h 41m

Chicago O'Hare Intl

Mon 5/25

7:30 am-10:50 am

Nonstop2h 20m

$275

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 5/23

6:55 am-3:30 pm

2 stops9h 35m

Chicago O'Hare Intl

Tue 5/26

1:35 pm-9:35 pm

1 stop7h 00m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
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

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 May 3, 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 May 2, 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 May 3, 2026.

The most flights from DU8 to CHI are scheduled on a Sunday (41 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (26 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 May 3, 2026.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,311 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,311 reviews
Southwest
8.0
Very good
4,311 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
9,682 reviews
Southwest
8.0
Very good
4,311 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
11,672 reviews
Southwest
8.0
Very good
4,311 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
7.1
Good
2,966 reviews
Southwest
8.0
Very good
4,311 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
5.6
Fair
2,968 reviews
Southwest
8.0
Very good
4,311 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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 4h 41m. Fly via Delta, United Airlines, or Southwest to get the fastest option. The distance from Durham to Chicago is about 645 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 $74 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%), United Airlines (84%), SWISS( 84%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $874, 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 $171 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

Traveling to a place near Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$75Average$194FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$307FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$314FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$160Average$293FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$171Average$344FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$303FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.