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$107+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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The best prices from Durham to Chicago are usually found in July or August, 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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(Mytrip)

One-way from

$107
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$318
Provider with most accurate pricing for Raleigh-Durham-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Raleigh-Durham-Chicago (CHI) flights.
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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. 16% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 21, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 4/69:53 pmRDU - ORD
1 stop12h 52mSpirit Airlines
Sun 4/1310:19 amORD - RDU
1 stop9h 34mSpirit Airlines
Deal found 2/20$183
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sat 5/178:31 pmRDU - MDW
1 stop27h 09mFrontier
Mon 5/191:19 pmMDW - RDU
1 stop5h 38mFrontier
Deal found 2/20$188
This CheapOair deal was found by Cheapflights users on 2/20. 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.
Wed 5/78:43 pmRDU - ORD
1 stop14h 12mMultiple Airlines
Fri 5/91:01 pmORD - RDU
Nonstop2h 04mMultiple Airlines
Deal found 2/20$197
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/163:01 pmRDU - ORD
Nonstop2h 20mFrontier
Sun 5/186:00 amORD - RDU
1 stop7h 01mFrontier
Deal found 2/20$266
This Delta deal was found by Cheapflights users on 2/20. 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 4/27:20 amRDU - MDW
2 stops11h 42mDelta
Tue 4/84:59 pmMDW - RDU
2 stops17h 23mDelta
Deal found 2/20$274
This Delta deal was found by Cheapflights users on 2/20. 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 2/278:59 amRDU - ORD
1 stop10h 42mDelta
Mon 3/37:30 amORD - RDU
1 stop9h 19mDelta
Deal found 2/20$277
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/49:55 amRDU - ORD
1 stop8h 05mJetBlue
Mon 3/101:15 pmORD - RDU
1 stop8h 50mJetBlue
Deal found 2/20$297
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 4/97:30 pmRDU - ORD
Nonstop2h 31mAmerican Airlines
Mon 4/143:51 pmORD - RDU
Nonstop2h 00mAmerican Airlines
Deal found 2/20$299
This Southwest deal was found by Cheapflights users on 2/20. 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 3/208:45 pmRDU - MDW
Nonstop2h 05mSouthwest
Mon 3/248:30 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 2/20$299
This Sun Country Air deal was found by Cheapflights users on 2/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/286:10 pmRDU - ORD
1 stop26h 02mSun Country Air
Mon 9/111:00 amORD - RDU
1 stop5h 32mSun Country Air
Deal found 2/20$315
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 3/128:55 amRDU - ORD
1 stop5h 10mSouthwest
Fri 3/147:00 amORD - RDU
1 stop4h 25mSouthwest
Deal found 2/20$336
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Mon 3/37:15 pmRDU - MDW
2 stops23h 20mMultiple Airlines
Thu 3/66:26 pmMDW - RDU
2 stops20h 38mMultiple Airlines
Deal found 2/20$544

Find flights from Durham to Chicago within your budget

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 February 21, 2025.

Fly from

Durham

Fly to

Chicago

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 4/6

9:53 pm-9:45 am

1 stop12h 52m

Chicago O'Hare Intl

Sun 4/13

10:19 am-8:53 pm

1 stop9h 34m

$183

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/17

8:31 pm-10:40 pm

1 stop27h 09m

Chicago Midway

Mon 5/19

1:19 pm-7:57 pm

1 stop5h 38m

$188

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 5/7

8:43 pm-9:55 am

1 stop14h 12m

Chicago O'Hare Intl

Fri 5/9

1:01 pm-4:05 pm

Nonstop2h 04m

$197

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 6/19

3:01 pm-4:38 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 6/22

12:37 pm-3:35 pm

Nonstop1h 58m

$251

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 3/5

6:00 am-6:41 pm

1 stop13h 41m

Chicago O'Hare Intl

Tue 3/18

6:00 am-3:03 pm

1 stop8h 03m

$263

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 4/2

7:20 am-6:02 pm

2 stops11h 42m

Chicago Midway

Tue 4/8

4:59 pm-11:22 am

2 stops17h 23m

$274

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 3/4

9:55 am-5:00 pm

1 stop8h 05m

Chicago O'Hare Intl

Mon 3/10

1:15 pm-11:05 pm

1 stop8h 50m

$297

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 4/9

7:30 pm-9:01 pm

Nonstop2h 31m

Chicago O'Hare Intl

Mon 4/14

3:51 pm-6:51 pm

Nonstop2h 00m

$299

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 3/20

8:45 pm-9:50 pm

Nonstop2h 05m

Chicago Midway

Mon 3/24

8:30 pm-11:20 pm

Nonstop1h 50m

$299

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 3/12

8:55 am-1:05 pm

1 stop5h 10m

Chicago O'Hare Intl

Fri 3/14

7:00 am-12:25 pm

1 stop4h 25m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 26 results
1
2
3

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.

Travel insights for flights from Durham to Chicago

Get recent, data-driven insights about flights from Durham to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Durham to Chicago, you should look to book at least 85 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 February 21, 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 Wednesday evenings when fares are most often at their lowest. Monday 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 February 21, 2025.

The most flights from DU8 to CHI are scheduled on a Thursday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 21, 2025.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,401 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,213 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,069 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,759 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $107. Frontier flights start at $109 while deals on JetBlue start at $123 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%), Royal Jordanian (91%), Republic Airways( 87%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $1,123, our data shows the cheapest flight currently is $148. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $98 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$125FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$80Average$249FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$137Average$325FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$142Average$364FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$159Average$322FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$339FlexibilityNo cancel feeOn-timeN/A
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