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 $52. Southwest flights start at $88 while deals on JetBlue start at $93 one-way.

Weekly flight availability from Durham to Chicago

The most flights from DU8 to CHI are scheduled on a Tuesday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

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.

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).

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 cheapest flights from Durham to Chicago?

While on average a flight from Durham to Chicago is generally $1,686, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $218 for that flight.

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: Emirates (100%), Japan Airlines (86%), SkyWest Airlines( 85%).

What are the most popular airlines that fly from Durham to Chicago?

The most popular airlines flying from Durham to Chicago are United Airlines, American Airlines and Frontier. Something to consider prior to booking your 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.

Find Cheap Flights from Durham to Chicago

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Cheapflights Tip: The best prices from Durham to Chicago are usually found in December or October, booked 76 days in advance, depart on a Thursday or Friday and return on a Friday

Find flight deals from Durham to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	July
Cheapest in	December
Average price	$335

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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Highest demand for flights based on searches. 14% potential increase in price ($49 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Cheapflights Insights

Everything you need to know about your flight from Durham to Chicago

Prices

Airlines

What is the cheapest time of day to fly from DU8 to CHI?

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 21% on airfare.

What is the cheapest day to fly from Durham to Chicago?

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.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Southwest

8.0

Very good

4,196 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

United Airlines

7.4

Good

10,228 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

JetBlue

7.1

Good

3,037 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

American Airlines

7.0

Good

12,075 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Frontier

5.6

Fair

2,579 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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 $52. Southwest flights start at $88 while deals on JetBlue start at $93 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: Emirates (100%), Japan Airlines (86%), SkyWest Airlines( 85%).
What are the cheapest flights from Durham to Chicago?
While on average a flight from Durham to Chicago is generally $1,686, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $218 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.

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Top 6 airlines flying from Durham to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$62	Average$217	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$88	Average$330	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$160	Average$327	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$183	Average$338	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$193	Average$324	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$207	Average$361	FlexibilityNo cancel fee	On-time63%

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Cheap flights from Durham, NC to Chicago (CHI)

Find cheap flights from Durham to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Durham to Chicago

Most accurate provider

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Popular in

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Average price

Cheapflights Insights

What is the cheapest time of day to fly from DU8 to CHI?

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 21% on airfare.

What is the cheapest day to fly from Durham to Chicago?

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

The most flights from DU8 to CHI are scheduled on a Tuesday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Durham to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What are the cheapest airlines to fly from Durham to Chicago one-way?

What are the most popular routes from Durham to Chicago?

What are the most reliable airlines from Durham to Chicago?

What are the cheapest flights from Durham to Chicago?

Can I find deals for flights from Durham to Chicago that include hotel bookings?

How can I find direct flights from Durham to Chicago?

Can I find deals for business class flights from Durham to Chicago?

Traveling to a place near Chicago?

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Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.

Complete your trip

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Search flights from Durham to Chicago by cabin class

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