$65 Find Cheap Flights from Chicago O'Hare Airport to Oregon

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Oregon departing on 12/4. 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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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon.
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Cheap Flights from O'Hare Intl to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$208
Eugene
Eugene1 stop$277
Redmond
Redmond1 stop$283
Medford
Medford1 stop$332
North Bend
North Bend1 stop$414
Boise
Boise1 stop$269
Portland
Portland1 stop$208
Eugene
Eugene1 stop$277
Redmond
Redmond1 stop$283
Medford
Medford1 stop$332
North Bend
North Bend1 stop$414
Boise
Boise1 stop$269

Book Cheap O'Hare Intl to Oregon Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Oregon 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 O'Hare Intl to Oregon

Sun, Nov 16 - Sun, Nov 16
Frontier Logo
6:00 am - 11:56 amORD-PDX
7h 56m1 stop
Frontier Logo
3:26 pm - 12:15 amPDX-ORD
6h 49m1 stop
$208Frontier
Find Deal
Sat, Dec 6 - Sat, Dec 13
Frontier Logo
2:26 pm - 11:56 amORD-PDX
23h 30m2 stops
Frontier Logo
9:48 am - 12:13 amPDX-ORD
12h 25m1 stop
$209Frontier
Find Deal
Thu, Dec 11 - Sun, Jan 18
Frontier Logo
7:00 am - 11:56 amORD-PDX
30h 56m1 stop
Frontier Logo
11:29 am - 10:38 amPDX-ORD
21h 09m1 stop
$210Frontier
Find Deal
Wed, Dec 10 - Tue, Dec 16
Alaska Airlines Logo
2:05 pm - 4:48 pmORD-PDX
4h 43mnonstop
Alaska Airlines Logo
7:04 am - 1:09 pmPDX-ORD
4h 05mnonstop
$217Alaska Airlines
Find Deal
Sat, Dec 13 - Sat, Jan 10
United Airlines Logo
9:05 am - 11:48 amORD-PDX
4h 43mnonstop
United Airlines Logo
1:24 pm - 9:15 pmPDX-ORD
5h 51m1 stop
$223United Airlines
Find Deal
Wed, Dec 10 - Tue, Dec 16
United Airlines Logo
6:55 am - 2:47 pmORD-PDX
9h 52m1 stop
United Airlines Logo
7:00 am - 1:02 pmPDX-ORD
4h 02mnonstop
$227United Airlines
Find Deal
Thu, Nov 27 - Wed, Dec 3
Alaska Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
Alaska Airlines Logo
10:30 am - 7:54 pmPDX-ORD
7h 24m1 stop
$236Alaska Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
American Airlines Logo
9:59 am - 1:06 pmORD-BOI
4h 07mnonstop
American Airlines Logo
1:36 pm - 6:19 pmBOI-ORD
3h 43mnonstop
$272American Airlines
Find Deal
Fri, Dec 5 - Sat, Dec 13
American Airlines Logo
10:25 am - 1:27 pmORD-BOI
4h 02mnonstop
American Airlines Logo
1:57 pm - 6:40 pmBOI-ORD
3h 43mnonstop
$273American Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Hawaiian Airlines Logo
8:55 am - 6:15 pmORD-EUG
11h 20m1 stop
Hawaiian Airlines Logo
9:00 am - 10:30 pmEUG-ORD
11h 30m1 stop
$342Hawaiian Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Oregon flights

Get data-powered insights and trends into flights from O'Hare Intl to Oregon to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Oregon flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Oregon from Chicago O'Hare Intl Airport found in the last 72 hours was to Portland, at $209 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Portland (PDX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $209.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Oregon?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $325, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Oregon?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Oregon, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Oregon is August, when tickets cost $293 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $469 and $394 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Oregon?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Oregon clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Oregon on a Wednesday and more expensive on a Monday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Friday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Oregon?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Oregon, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Oregon, you should book around 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$65
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago O'Hare Airport to Boise

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Oregon?

    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 O'Hare Airport to Oregon.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Oregon 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 O'Hare Airport to Oregon?

    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 from Chicago O'Hare Airport to Oregon with an airline and back with another airline.

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

    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 from Chicago O'Hare Airport to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Oregon?

    The cheapest time of day to fly to Oregon is generally at night, when round-trip flights cost $325 on average. Morning departures are around 13% cheaper than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $488.

Reviews of the top 5 airlines serving from O'Hare Intl to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oregon. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Oregon? 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.
8.0
Alaska AirlinesOverall score based on 11210 reviews
8.1Boarding
8.5Crew
7.1Food
7.8Comfort
7.0Entertainment
Airline reviews

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

4.0 OkayAnonymous, Oct 2025LAX - MFR
Read more Alaska Airlines reviews

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

Late. Too long a flight for a 737. 0.5 oz of pretzels for a 5+ hour flight at dinner time. One step above Ryan Air/ several below Delta.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight delay caused me to miss my connecting flight home, but I was put up at a nearby motel, and it was great

My seat. The reprentative on the phone was bad. The passengers screamed at each other and no one stopped them. The directions boarding the plane were unclear. There was a medical incident and the ICU nurse present said the women was having a cardic incident. Cooler heads determined it was a UTI. I had a allergy attack and a guy got a mask from the flight attendent and told me to wear it. He "had kidney failure". Why didnt they tell him to wear the mask, why was he even on the plane? It was embarrassing, he said hurtful things. By the way, I have a degree in Medical Micrbiology from Northwestern Medical school. MT(ASCP). Look it up. I Know the difference between allergies and an infection. But we had to listen to the unstable screaming man.

My flight got canceled never left san diego and miss out my fam event

Terrible. My flight was pushed out three times finally the fourth time it was canceled completely. They sent me to a hotel that would not accept the voucher. And I had to pay for my cab and Uber . I arrived at the airport at five and didn’t get into my hotel until 1145.

Wouldve liked a meal option (that you didnt have to prepay for) for such a long flight. But otherwise staff was friendly and boarding/un boarding was as efficient as it could be

The flight attendants were friendly. I liked that I got a mini soda can, not just a small cup. No issues with our flight departure, etc.

5 hours delay, while seated moved passengers around on the plane. We were out on the runway, had to return to the gate. Changed tires.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The flight was CANCELED!!! Can’t get much more “poor” than that. I had to switch to American Airlines, add another layover and got home in Honolulu 4 hours later than I was supposed to be home. One bright spot was Josh with Alaska Airlines at SFO. He got me on a United Flight that got me home a few hours before I would have. Without him I would have gotten home almost 7 hours after my originally scheduled flight.

Canceled my flight within 24 hours, causing me arriving home midnight. Will never book Hawaiian airlines anymore

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

I always love flying Hawaii and I have nothing to add

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

I received several emails about my 3:10 flight. When I showed up to the airport at 12:30 to check my bags I was told the flight was actually at 1 pm. They grudgingly rebooked me for a flight at 5:22 to Vegas to get a connecting to LAX. I did find the gate for my original 3:10 flight but they were booked. I proceeded to receive status updates and gate change information for the 3:10 flight, even though I was apparently never supposed to be on that flight

My flight was delayed three hours and then cancelled. The gate agent proceeded to rebook me in a middle seat without telling me and I was placed between two large individuals who did not fit in their own seats and instead took up most of mine. It was an awful experience.

The food options were limited and very specific. Some type of entertainment option for a 4.5 hour flight would have been nice.

Flight was smooth and comfortable. We were able to check a bag at counter due to full flight and boarded with an earlier group. We were there very early and didn’t hear the gate change just noticed our flight was no longer displayed st the gate. There were two other flights with gate shuffles - may be unavoidable but not desirable. First time I had to print my own luggage tag and attach at arrival. Not a fan of that process.

The crew was EXTREMELY helpful And sweet and the flight was smooth!

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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