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$84+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
RDU — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$176
(Cheapflightsfares)

One-way from

$84
(FlightHub)

Popular in

March

Cheapest in

August

Average price

$256
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)
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/313:06 pmRDU - ORD
1 stop5h 42mFrontier
Mon 6/211:32 amORD - RDU
Nonstop2h 07mFrontier
Deal found 4/30$176
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Thu 8/73:26 pmRDU - ORD
Nonstop2h 25mMultiple Airlines
Sun 8/108:00 amORD - RDU
1 stop10h 48mMultiple Airlines
Deal found 5/1$177
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/289:20 amRDU - ORD
Nonstop2h 24mUnited Airlines
Sat 5/316:28 pmORD - RDU
Nonstop2h 07mUnited Airlines
Deal found 4/30$179
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 6/58:50 amRDU - ORD
1 stop6h 16mSpirit Airlines
Sun 6/87:35 pmORD - RDU
1 stop12h 37mSpirit Airlines
Deal found 5/1$181
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:00 amRDU - ORD
Nonstop2h 21mAmerican Airlines
Wed 5/2810:56 amORD - RDU
Nonstop2h 05mAmerican Airlines
Deal found 4/30$184
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:15 amRDU - MDW
Nonstop2h 05mSouthwest
Wed 5/286:30 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 4/30$189
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1411:08 amRDU - ORD
1 stop4h 39mDelta
Tue 6/247:05 amORD - RDU
1 stop3h 59mDelta
Deal found 4/30$197
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/145:20 amRDU - MDW
1 stop5h 21mDelta
Tue 6/241:09 pmMDW - RDU
1 stop3h 29mDelta
Deal found 4/29$197
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 5/245:42 pmRDU - MDW
1 stop5h 20mFrontier
Wed 5/286:40 amMDW - RDU
1 stop11h 19mFrontier
Deal found 4/30$198
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/185:25 pmRDU - ORD
1 stop26h 44mSun Country Air
Fri 5/236:12 pmORD - RDU
1 stop15h 36mSun Country Air
Deal found 4/30$235
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:05 amRDU - ORD
2 stops9h 55mSouthwest
Wed 6/254:00 pmORD - RDU
1 stop5h 15mSouthwest
Deal found 4/30$254
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/305:45 pmRDU - RFD
2 stops15h 21mMultiple Airlines
Sun 6/14:16 pmRFD - RDU
2 stops15h 56mMultiple Airlines
Deal found 4/30$259

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 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

Sat 5/31

3:06 pm-7:48 pm

1 stop5h 42m

Chicago O'Hare Intl

Mon 6/2

11:32 am-2:39 pm

Nonstop2h 07m

$176

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 8/7

3:26 pm-4:51 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 8/10

8:00 am-7:48 pm

1 stop10h 48m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 5/28

9:20 am-10:44 am

Nonstop2h 24m

Chicago O'Hare Intl

Sat 5/31

6:28 pm-9:35 pm

Nonstop2h 07m

$179

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 6/5

8:50 am-2:06 pm

1 stop6h 16m

Chicago O'Hare Intl

Sun 6/8

7:35 pm-9:12 am

1 stop12h 37m

$181

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 5/28

6:00 am-7:21 am

Nonstop2h 21m

Chicago O'Hare Intl

Wed 5/28

10:56 am-2:01 pm

Nonstop2h 05m

$184

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 5/28

6:15 am-7:20 am

Nonstop2h 05m

Chicago Midway

Wed 5/28

6:30 pm-9:20 pm

Nonstop1h 50m

$189

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 6/14

11:08 am-2:47 pm

1 stop4h 39m

Chicago O'Hare Intl

Tue 6/24

7:05 am-12:04 pm

1 stop3h 59m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 6/14

5:20 am-9:41 am

1 stop5h 21m

Chicago Midway

Tue 6/24

1:09 pm-5:38 pm

1 stop3h 29m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/24

5:42 pm-10:02 pm

1 stop5h 20m

Chicago Midway

Wed 5/28

6:40 am-6:59 pm

1 stop11h 19m

$198

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 5/18

5:25 pm-7:09 pm

1 stop26h 44m

Chicago O'Hare Intl

Fri 5/23

6:12 pm-10:48 am

1 stop15h 36m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 27 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 April 25, 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 $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 May 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 May 1, 2025.

The most flights from DU8 to CHI are scheduled on a Monday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 May 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
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $84. United Airlines flights start at $85 while deals on Southwest start at $85 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%), Republic Airways (88%), ANA( 85%).

  • What are the cheapest flights from Durham to Chicago?

    While on average a flight from Durham to Chicago is generally $928, our data shows the cheapest flight currently is $80. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $127 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
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$143FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$98Average$263FlexibilityNo cancel feeOn-time65%
DeltaCheapest$102Average$339FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$140Average$316FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$146Average$363FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$162Average$331FlexibilityNo cancel feeOn-time63%

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