$104 Find Cheap Flights from Chicago O'Hare Airport to Oregon - 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 O'Hare Intl to Oregon departing on 12/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Oregon

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from O'Hare Intl to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$312
Eugene
Eugene1 stop$297
Redmond
Redmond1 stop$367
Medford
Medford1 stop$345
North Bend
North Bend1 stop$349
Boise
Boise1 stop$340
Portland
Portlandnonstop$312
Eugene
Eugene1 stop$297
Redmond
Redmond1 stop$367
Medford
Medford1 stop$345
North Bend
North Bend1 stop$349
Boise
Boise1 stop$340

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

Tue, Oct 20 - Tue, Oct 27
Delta Logo
6:00 pm - 11:47 pm
ORD
-
EUG
7h 47m
1 stop
Delta Logo
6:15 am - 5:14 pm
EUG
-
ORD
8h 59m
1 stop
$297Delta
Tue, Oct 20 - Tue, Oct 27
Delta Logo
9:30 am - 3:58 pm
ORD
-
EUG
8h 28m
2 stops
Delta Logo
6:15 am - 5:14 pm
EUG
-
ORD
8h 59m
1 stop
$302Delta
Mon, Aug 3 - Fri, Aug 7
American Airlines Logo
10:15 pm - 12:50 am
ORD
-
PDX
4h 35mnonstop
American Airlines Logo
5:59 am - 12:12 pm
PDX
-
ORD
4h 13mnonstop
$312American Airlines
Thu, Jul 2 - Mon, Jul 6
Frontier Logo
7:20 am - 5:24 pm
ORD
-
PDX
12h 04m
1 stop
Frontier Logo
5:49 pm - 5:37 am
PDX
-
ORD
9h 48m
1 stop
$314Frontier
Sat, Aug 8 - Sat, Aug 15
Alaska Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Alaska Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
$315Alaska Airlines
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
10:15 pm - 12:50 am
ORD
-
PDX
4h 35mnonstop
American Airlines Logo
11:15 pm - 5:14 am
PDX
-
ORD
3h 59mnonstop
$316American Airlines
Fri, Jul 31 - Fri, Aug 7
Alaska Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Alaska Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
$317Alaska Airlines
Fri, Jul 3 - Tue, Jul 7
United Airlines Logo
3:26 pm - 10:59 pm
ORD
-
EUG
9h 33m
1 stop
United Airlines Logo
12:50 pm - 7:00 pm
EUG
-
ORD
4h 10mnonstop
$319United Airlines
Sat, Jun 27 - Tue, Jul 7
Frontier Logo
9:48 pm - 4:57 pm
ORD
-
PDX
21h 09m
1 stop
Frontier Logo
5:16 pm - 8:52 pm
PDX
-
ORD
25h 36m
1 stop
$320Frontier
Tue, Sep 29 - Wed, Sep 30
United Airlines Logo
7:00 am - 9:31 am
ORD
-
PDX
4h 31mnonstop
United Airlines Logo
12:45 pm - 9:18 pm
PDX
-
ORD
6h 33m
1 stop
$321United Airlines
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Oregon?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Oregon departing in August.

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 5 days was to Portland, at $308 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 5 days was $308.

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

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Oregon depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Oregon is generally at night, when round-trip flights cost $334 on average. Morning departures are around 10% 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 $458.

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 $446, 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 $94 (return) on average. On the other hand, the most expensive months are June and February, when the average cost of round-trip tickets is $742 and $180 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 Tuesday and more expensive on a Sunday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Wednesday, and avoid Mondays 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 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$104
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 20% 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.

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.
7.9
Alaska AirlinesOverall score based on 12522 reviews
7.1Food
8.1Boarding
8.5Crew
7.8Comfort
7.0Entertainment
Airline reviews

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

10.0 ExcellentAnonymous, Jun 2026
LAX - EUG
Read more Alaska Airlines reviews

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

Flight delayed Didn’t send second leg of trip itemerary First class was fair, but not great.

Short trip, was nice to have a drink on the short flight still.

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Couldn’t order food for the family because all the good food was unavailable. We opted for bringing something on with us. I also didn’t like that I had to have T-mobile for online movies. Stupid.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

The flight crew home was so, so friendly and HILARIOUS. I’ll keep flying Alaska like I have for the last 30+ years!

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

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.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

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.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight from O'Hare Intl to Oregon

Information on your arrival and departure airports