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. JetBlue flights start at $93 while deals on American Airlines 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 (15 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 $1,711, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $201 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

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Durham to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Durham to Chicago are usually found in December or April, 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	$342

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

Highest demand for flights based on searches. 13% potential increase in price ($47 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 2026

Search Deals

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

4,203 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

4,203 reviews

Southwest

8.0

Very good

4,203 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

10,260 reviews

Southwest

8.0

Very good

4,203 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

3,042 reviews

Southwest

8.0

Very good

4,203 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

12,097 reviews

Southwest

8.0

Very good

4,203 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

2,567 reviews

Southwest

8.0

Very good

4,203 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. JetBlue flights start at $93 while deals on American Airlines 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 $1,711, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Raleigh-Durham - Chicago O'Hare Intl), you can expect to pay $201 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

Benton Harbor

Lansing

Merrillville

Valparaiso

Hammond

Saint Joseph

Porter

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Chicago flight routes

Complete your trip

Flights by cabin class

Other flight options

Popular flights

Top destinations

Alternative routes for Durham to Chicago

Raleigh to O'Hare Intl flights

Charlotte to O'Hare Intl flights

Raleigh to Midway flights

Norfolk to O'Hare Intl flights

Asheville to O'Hare Intl flights

Knoxville to O'Hare Intl flights

Greensboro to O'Hare Intl flights

Charlotte to St. Louis flights

Norfolk to Midway flights

Asheville to Midway flights

Raleigh to St. Louis flights

Greensboro to Midway flights

Wilmington to O'Hare Intl flights

Norfolk to St. Louis flights

Myrtle Beach to O'Hare Intl flights

Raleigh to Peoria flights

Greensboro to St. Louis flights

Charlotte to Peoria flights

Knoxville to Midway flights

Knoxville to St. Louis flights

Raleigh to Rockford flights

Charlotte to Bloomington flights

Blountville to O'Hare Intl flights

Charlotte to Moline flights

Myrtle Beach to Midway flights

Wilmington to Midway flights

Raleigh to Moline flights

Asheville to Peoria flights

Charlotte to Rockford flights

Fayetteville to O'Hare Intl flights

Myrtle Beach to Peoria flights

Asheville to St. Louis flights

Myrtle Beach to St. Louis flights

Fayetteville to Midway flights

Raleigh to Evansville flights

Norfolk to Moline flights

Wilmington to St. Louis flights

Knoxville to Peoria flights

Fayetteville to St. Louis flights

Blountville to St. Louis flights

Raleigh to Bloomington flights

Raleigh to Dubuque flights

New Bern to St. Louis flights

Myrtle Beach to Moline flights

Greensboro to Peoria flights

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$336	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$160	Average$327	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$186	Average$340	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$203	Average$326	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$233	Average$366	FlexibilityNo cancel fee	On-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

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

Most trusted provider

Popular in

Cheapest in

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 (15 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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Durham to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

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 30, 2026.

Complete your trip

Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Durham to Chicago by cabin class

Find flights from Durham to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Durham and Chicago flights

Browse other Durham and Chicago flight options. Last updated on September 30, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Durham to Chicago flights

Consider these flights traveling from Durham to Chicago.

Top 6 airlines flying from Durham to Chicago

100% Free

Book with Flexibility

Travel Smart