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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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Jun 1 — Jun 81
Mon 6/1
Mon 6/8
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 May 2, 2026.

This Frontier deal was found by Cheapflights users on 4/27. 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 5/1212:59 pm
RDU
-
ORD
1 stop7h 52m
Frontier
Thu 5/148:39 am
ORD
-
RDU
Nonstop2h 19m
Frontier
Deal found 4/27$194
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 4/27. 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 6/1212:10 pm
RDU
-
ORD
1 stop20h 53m
Multiple Airlines
Wed 6/177:52 am
ORD
-
RDU
2 stops15h 29m
Multiple Airlines
Deal found 4/27$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.
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 4/27. 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.
Mon 5/43:42 pm
RDU
-
MDW
1 stop7h 37m
Frontier
Fri 5/1512:04 pm
MDW
-
RDU
1 stop11h 20m
Frontier
Deal found 4/27$201
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 4/27. 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 5/277:52 pm
RDU
-
MDW
2 stops19h 20m
Frontier
Wed 6/312:04 pm
MDW
-
RDU
1 stop11h 29m
Frontier
Deal found 4/27$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

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 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$194
(Frontier)

One-way from

$101
(Cheapflightsfares)

Popular in

February

Cheapest in

December

Average price

$294
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 ($44 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 2, 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 - MDW

RDUMDW

Raleigh-Durham

Tue 6/2

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Wed 6/10

11:25 am-2:15 pm

Nonstop1h 50m

$237

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

Tue 6/2

11:25 am-4:45 pm

1 stop6h 20m

Chicago Midway

Wed 6/3

7:40 am-10:30 am

Nonstop1h 50m

$247

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/30

3:55 pm-4:55 pm

Nonstop2h 00m

Chicago Midway

Sat 6/6

6:15 pm-9:10 pm

Nonstop1h 55m

$265

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Thu 6/4

3:20 pm-7:45 am

1 stop17h 25m

Chicago Greater Rockford

Fri 6/5

7:53 pm-9:00 am

1 stop12h 07m

$277

RaleighChicago

RDU - RFD

RDURFD

Raleigh-Durham

Fri 5/22

7:49 pm-9:21 am

1 stop14h 32m

Chicago Greater Rockford

Sun 5/24

11:27 am-12:24 am

2 stops11h 57m

$280

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 5/26

11:25 am-3:45 pm

2 stops5h 20m

Chicago Midway

Tue 6/2

10:10 am-5:15 pm

2 stops6h 05m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 60 resultsSorted by cheapest first
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2
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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

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 2, 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 25, 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 2, 2026.

The most flights from DU8 to CHI are scheduled on a Monday (38 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 2, 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
4,314 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
9,686 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
11,677 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
2,967 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
5.7
Fair
2,972 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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 2h. Fly via Southwest or United Airlines to get the fastest option. The distance from Durham to Chicago is about 631 mi. Generally, flights for this route are nonstop.

  • 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: 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 $954, 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
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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 May 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$194FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$303FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$313FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$160Average$293FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$171Average$344FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$310FlexibilityNo cancel feeOn-time63%

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