$79 Find Cheap Flights from Chicago 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 Chicago to Oregon departing on 7/1. 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

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.
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Flights Deals

Best Oregon Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$172
Eugene
Eugene1 stop$224
Redmond
Redmond1 stop$222
Medford
Medford1 stop$206
Boise
Boise1 stop$181
Portland
Portland1 stop$172
Eugene
Eugene1 stop$224
Redmond
Redmond1 stop$222
Medford
Medford1 stop$206
Boise
Boise1 stop$181

Cheap Flights from Chicago to Oregon

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

Wed, Jul 9 - Tue, Jul 15
Spirit Airlines Logo
7:08 am - 2:15 pmORD-PDX
9h 07m1 stop
Spirit Airlines Logo
3:10 pm - 6:03 amPDX-ORD
12h 53m1 stop
$172Spirit Airlines
Find Deal
Tue, Jul 1 - Tue, Jul 8
Spirit Airlines Logo
11:50 am - 5:44 pmORD-PDX
7h 54m1 stop
Spirit Airlines Logo
6:39 pm - 6:03 amPDX-ORD
9h 24m1 stop
$174Spirit Airlines
Find Deal
Tue, Aug 26 - Sun, Aug 31
Alaska Airlines Logo
2:07 pm - 4:36 pmORD-PDX
4h 29mnonstop
Alaska Airlines Logo
11:00 pm - 5:00 amPDX-ORD
4h 00mnonstop
$180Alaska Airlines
Find Deal
Sat, Aug 9 - Sat, Aug 16
United Airlines Logo
4:13 pm - 6:45 pmORD-PDX
4h 32mnonstop
United Airlines Logo
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
$181United Airlines
Find Deal
Wed, Sep 10 - Sat, Sep 13
Southwest Logo
8:30 am - 10:50 amMDW-PDX
4h 20mnonstop
Southwest Logo
6:00 am - 12:00 pmPDX-MDW
4h 00mnonstop
$181Southwest
Find Deal
Tue, Sep 16 - Sat, Sep 20
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
Southwest Logo
11:00 am - 7:05 pmPDX-MDW
6h 05m1 stop
$191Southwest
Find Deal
Sun, Aug 31 - Sun, Sep 7
Alaska Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
Alaska Airlines Logo
11:00 pm - 5:00 amPDX-ORD
4h 00mnonstop
$200Alaska Airlines
Find Deal
Mon, Aug 18 - Thu, Aug 28
United Airlines Logo
6:30 am - 12:10 pmORD-EUG
7h 40m1 stop
United Airlines Logo
3:59 pm - 11:59 pmEUG-ORD
6h 00m1 stop
$239United Airlines
Find Deal
Sat, Oct 25 - Wed, Oct 29
American Airlines Logo
9:45 am - 12:44 pmORD-BOI
3h 59mnonstop
American Airlines Logo
1:17 pm - 5:54 pmBOI-ORD
3h 37mnonstop
$255American Airlines
Find Deal
Sat, Jul 26 - Tue, Jul 29
American Airlines Logo
7:25 am - 9:49 amORD-PDX
4h 24mnonstop
American Airlines Logo
11:54 pm - 5:50 amPDX-ORD
3h 56mnonstop
$272American Airlines
Find Deal
Useful Info

KAYAK's insights & trends for Chicago to Oregon flights

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

What is the cheapest Chicago to Oregon flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Oregon.

The cheapest ticket to Oregon from Chicago found in the last 72 hours was to Portland, at $207 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 $207.

Can I save money by flying with a layover from Chicago 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $433 on average.

What is the cheapest month to fly from Chicago to Oregon?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Oregon is September, when tickets cost $267 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $425 and $418 respectively.

What’s the cheapest day of the week to fly from Chicago to Oregon?

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

When flying from Chicago to Oregon, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

How far in advance should I book a flight from Chicago 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 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 to Oregon, you should book around 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$79
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago O'Hare Airport to Portland

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Chicago 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 to Oregon.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 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 $248 on average. Morning departures are around 9% 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 $381.

Top 5 airlines serving from Chicago 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 Chicago 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 10000 reviews
8.5Crew
7.1Food
7.8Comfort
7.1Entertainment
8.1Boarding
Airline reviews

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

6.0 GoodAnonymous, Jun 2025OGG - PDX
Read more Alaska Airlines reviews

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

It was a quick flight, but coffee would have been great!

I can honestly say in the 54 years of my life this was the worst flying experience I have ever had. I was delayed on the tarmac going into Dallas for an hour and 2 hours on the tarmac leaving Dallas. a 4 hour flight turned into a 6 hour flight due to Alaska incompetence. To be honest I will never take another Alaska flight.

So much better coming back to Seattle than my trip TO Chicago. This crew actually communicated with the passengers!! Rebecca, one of the crew, stopped and visited with me about sign language. She should get a bonus of some kind!! She's a very neat gal!! It was still warm inside the plane, but it was packed! I still think you could do better than those teeny tiny pretzels! These were spicy and tasted terrible! All in all, still a better ride coming home. Go Seahawks!!

Arrival delay waiting for another flight to be towed and deboarded

I am mobility challenged and ground crew were accommodating to my needs. One must walk up a ramp to board Alaska planes. Terminal to tarmac to ramp to plane.

The attendances were very thorough and pleasant during the entire trip. The pilots did an excellent job keeping us posted on what to expect. The landing in Portland was executed professionally and perfectly. Boarding was delayed a half hour. But given the times were in, that was no surprise. All in all, my preference is to fly only Alaska Airlines for their reliability and professional service.

Awesome just like that we have a timeline flying Alaska.

All good! No entertainment on this new plane yet but ok for this short flight. Great on time flight! Thanks

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

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

Cabin class types available on flights to Oregon

Cabin classes available on flights to Oregon. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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