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$145+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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Cheapflights Tip: The best prices from Durham to Chicago are usually found in August or July, booked 32 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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(United Airlines)

One-way from

$145
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$268
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)
Search Deals
One-way flight from Durham to Chicago (CHI)
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Highest demand for flights based on searches. 19% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 1, 2025.

This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/279:20 amRDU - ORD
Nonstop2h 24mUnited Airlines
Sun 6/111:03 amORD - RDU
Nonstop2h 07mUnited Airlines
Deal found 3/31$241
This Justfly.com deal was found by Cheapflights users on 4/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1610:17 amRDU - ORD
1 stop9h 23mMultiple Airlines
Mon 5/194:15 pmORD - RDU
1 stop29h 04mMultiple Airlines
Deal found 4/1$242
This CheapOair deal was found by Cheapflights users on 4/1. 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 5/211:45 amRDU - ORD
1 stop6h 56mSpirit Airlines
Sun 5/47:33 pmORD - RDU
1 stop14h 07mSpirit Airlines
Deal found 4/1$244
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 6/612:56 pmRDU - ORD
1 stop5h 39mAmerican Airlines
Wed 6/116:55 pmORD - RDU
Nonstop2h 04mAmerican Airlines
Deal found 4/1$246
This Southwest deal was found by Cheapflights users on 4/1. 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.
Tue 8/51:35 pmRDU - MDW
Nonstop1h 55mSouthwest
Tue 8/1210:00 amMDW - RDU
Nonstop1h 55mSouthwest
Deal found 4/1$247
This Delta deal was found by Cheapflights users on 4/1. 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.
Sat 6/2812:26 pmRDU - MDW
1 stop4h 13mDelta
Tue 7/16:00 amMDW - RDU
1 stop4h 21mDelta
Deal found 4/1$248
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Thu 6/193:38 pmRDU - ORD
Nonstop2h 37mFrontier
Sun 6/2211:32 amORD - RDU
Nonstop2h 07mFrontier
Deal found 4/1$249
This Frontier deal was found by Cheapflights users on 4/1. 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 5/225:15 amRDU - MDW
1 stop4h 45mFrontier
Tue 5/276:35 amMDW - RDU
1 stop8h 34mFrontier
Deal found 4/1$249
This Sun Country Air deal was found by Cheapflights users on 3/31. 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.
Wed 5/147:45 pmRDU - ORD
1 stop24h 24mSun Country Air
Fri 5/168:05 pmORD - RDU
1 stop13h 43mSun Country Air
Deal found 3/31$255
This Delta deal was found by Cheapflights users on 4/1. 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 7/35:45 amRDU - ORD
1 stop5h 12mDelta
Thu 7/107:10 amORD - RDU
1 stop4h 42mDelta
Deal found 4/1$257
This Southwest deal was found by Cheapflights users on 3/31. 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.
Sat 6/75:45 amRDU - ORD
2 stops11h 40mSouthwest
Tue 6/101:50 pmORD - RDU
1 stop4h 05mSouthwest
Deal found 3/31$295

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 1, 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

Tue 5/27

9:20 am-10:44 am

Nonstop2h 24m

Chicago O'Hare Intl

Sun 6/1

11:03 am-2:10 pm

Nonstop2h 07m

$241

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 5/16

10:17 am-6:40 pm

1 stop9h 23m

Chicago O'Hare Intl

Mon 5/19

4:15 pm-10:19 pm

1 stop29h 04m

$242

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 5/2

11:45 am-5:41 pm

1 stop6h 56m

Chicago O'Hare Intl

Sun 5/4

7:33 pm-10:40 am

1 stop14h 07m

$244

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 6/6

12:56 pm-5:35 pm

1 stop5h 39m

Chicago O'Hare Intl

Wed 6/11

6:55 pm-9:59 pm

Nonstop2h 04m

$246

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 6/28

12:26 pm-3:39 pm

1 stop4h 13m

Chicago Midway

Tue 7/1

6:00 am-11:21 am

1 stop4h 21m

$248

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 6/19

3:38 pm-5:15 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 6/22

11:32 am-2:39 pm

Nonstop2h 07m

$249

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 5/22

5:15 am-9:00 am

1 stop4h 45m

Chicago Midway

Tue 5/27

6:35 am-4:09 pm

1 stop8h 34m

$249

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 6/30

3:10 pm-4:10 pm

Nonstop2h 00m

Chicago Midway

Wed 7/9

5:00 pm-7:50 pm

Nonstop1h 50m

$253

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 5/14

7:45 pm-7:09 pm

1 stop24h 24m

Chicago O'Hare Intl

Fri 5/16

8:05 pm-10:48 am

1 stop13h 43m

$255

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 7/3

5:45 am-9:57 am

1 stop5h 12m

Chicago O'Hare Intl

Thu 7/10

7:10 am-12:52 pm

1 stop4h 42m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 26 results
1
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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 March 28, 2025.

To ensure you get the cheapest price possible for a flight from Durham to Chicago, you should look to book at least 32 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 $323). 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 April 1, 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 April 1, 2025.

The most flights from DU8 to CHI are scheduled on a Monday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 April 1, 2025.
Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,277 reviews

Boarding

8.2

Comfort

8.0

Crew

8.7

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,277 reviews
Southwest
8.0
Very good
4,277 reviews

Boarding

8.2

Comfort

8.0

Crew

8.7

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,277 reviews

Boarding

8.2

Comfort

8.0

Crew

8.7

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,277 reviews

Boarding

8.2

Comfort

8.0

Crew

8.7

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,277 reviews

Boarding

8.2

Comfort

8.0

Crew

8.7

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Sun Country Air
6.9
Okay
349 reviews
Southwest
8.0
Very good
4,277 reviews

Boarding

8.2

Comfort

8.0

Crew

8.7

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $145. Frontier flights start at $146 while deals on United Airlines start at $149 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: Japan Airlines (93%), Cathay Pacific (90%), Royal Jordanian( 89%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $2,054, our data shows the cheapest flight currently is $134. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $139 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 $323). 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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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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$130FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$98Average$249FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$138Average$333FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$145Average$367FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$166Average$334FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$361FlexibilityNo cancel feeOn-timeN/A

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