$119 Find Cheap Flights from Chicago to Durham - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Durham departing on 7/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$238
Typical prices: $177-$317
Frontier
Thu 8/20Sun 8/23
ORD - RDU • 1 stop
Cheapest non-stop
$253
Typical prices: $220-$400
Southwest
Sat 8/8Mon 8/10
MDW - RDU • Non-stop
Arrival airport
You can't fly directly to Durham. It is served by Raleigh (RDU), located 10.1 miles from Durham.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Durham (CHI-RDU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Durham that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Durham

Thu, Aug 20 - Sun, Aug 23
Frontier Logo
8:05 am - 9:15 pm
ORD
-
RDU
12h 10m
1 stop
Frontier Logo
3:47 pm - 1:00 pm
RDU
-
ORD
22h 13m
1 stop
$238Frontier
Tue, Jul 21 - Sat, Jul 25
Frontier Logo
12:11 pm - 12:04 am
MDW
-
RDU
10h 53m
1 stop
Frontier Logo
6:15 am - 11:07 am
RDU
-
MDW
5h 52m
1 stop
$240Frontier
Thu, Aug 20 - Tue, Aug 25
Frontier Logo
8:05 am - 9:15 pm
ORD
-
RDU
12h 10m
1 stop
Frontier Logo
12:53 pm - 11:08 pm
RDU
-
ORD
11h 15m
1 stop
$240Frontier
Thu, Aug 27 - Mon, Aug 31
Frontier Logo
11:50 am - 11:59 pm
MDW
-
RDU
11h 09m
1 stop
Frontier Logo
1:21 pm - 8:31 pm
RDU
-
MDW
8h 10m
1 stop
$241Frontier
Thu, Sep 24 - Tue, Oct 6
Frontier Logo
2:03 pm - 12:17 am
ORD
-
RDU
9h 14m
1 stop
Frontier Logo
6:35 am - 12:02 pm
RDU
-
ORD
6h 27m
1 stop
$241Frontier
Sat, Aug 1 - Mon, Aug 3
Multiple Airlines Logo
1:50 pm - 12:03 am
ORD
-
RDU
9h 13m
1 stop
Multiple Airlines Logo
8:29 pm - 11:10 pm
RDU
-
ORD
27h 41m
1 stop
$244Multiple Airlines
Sun, Aug 2 - Fri, Aug 7
Multiple Airlines Logo
8:05 am - 5:09 pm
ORD
-
RDU
8h 04m
1 stop
Multiple Airlines Logo
10:59 am - 12:15 pm
RDU
-
ORD
26h 16m
2 stops
$246Multiple Airlines
Tue, Jul 21 - Wed, Jul 22
American Airlines Logo
1:17 pm - 7:18 pm
ORD
-
RDU
5h 01m
1 stop
American Airlines Logo
7:08 am - 8:30 am
RDU
-
ORD
2h 22mnonstop
$247American Airlines
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
7:40 am - 10:35 am
MDW
-
RDU
1h 55mnonstop
Southwest Logo
10:25 am - 3:50 pm
RDU
-
MDW
6h 25m
1 stop
$247Southwest
Tue, Jul 14 - Sat, Jul 18
Southwest Logo
10:10 am - 5:30 pm
MDW
-
RDU
6h 20m
2 stops
Southwest Logo
6:35 pm - 7:40 pm
RDU
-
MDW
2h 05mnonstop
$252Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$119
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago Midway Airport to Raleigh

When to book flights from Chicago to Durham

Are your dates flexible? Find out the best times to travel from Chicago to Durham based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Durham

  • Which airports will I be using when flying from Chicago to Durham?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Durham does not have its own airport so you’ll be flying into nearby Raleigh-Durham airport, which is 10.1 mi away.

  • How long does a flight from Chicago to Durham take?

    Direct flights cover the 630 miles separating Chicago and Durham in about 1h 50m.

  • How many flights are there between Chicago and Durham?

    39 direct flights run between Chicago and Durham on a daily basis. On average, there are about 273 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Durham?

    Consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Fridays.

  • How does KAYAK find such low prices on flights from Chicago to Durham?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Durham.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Durham?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Durham from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Durham?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Durham with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Durham?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Durham from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Durham?

    In the last 5 days, the cheapest one-way ticket between Chicago and Durham found on KAYAK was with Frontier for $53. Frontier offered a round-trip connection from $71 and JetBlue from $166.

Top tips for finding cheap flights from Chicago to Durham

  • There is no airport in Durham. Instead, you’ll be flying into Raleigh-Durham Airport when flying between Chicago and Durham.
  • The cheapest flight from Chicago to Durham was found 63 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be December, January and February. The cheapest month to fly is October.

Reviews of the top 4 airlines serving Chicago to Durham

 
Need help choosing which airline to fly with from Chicago to Durham? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4242 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Crew was kind of grumpy and there was no beverage service at all. Sodas were $4. Disappointing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

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

Complete your trip to Durham with a hotel stay or car rental