$127 Find Cheap Flights from Chicago 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 Chicago to Oregon departing on 9/10. 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.
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Cheap Flights from Chicago to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$311
Eugene
Eugenenonstop$329
Redmond
Redmond1 stop$413
Medford
Medford2 stops$328
Boise
Boise1 stop$335
Portland
Portlandnonstop$311
Eugene
Eugenenonstop$329
Redmond
Redmond1 stop$413
Medford
Medford2 stops$328
Boise
Boise1 stop$335

Book Cheap Chicago 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 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

Thu, Aug 6 - Wed, Aug 12
Multiple Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Multiple Airlines Logo
5:21 pm - 8:52 pm
PDX
-
ORD
25h 31m
1 stop
$311Multiple Airlines
Thu, Aug 6 - Sat, Aug 15
Multiple Airlines Logo
9:13 pm - 11:35 am
ORD
-
PDX
16h 22m
1 stop
Multiple Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
$312Multiple Airlines
Fri, Aug 14 - Tue, Aug 18
United Airlines Logo
10:25 am - 1:10 pm
ORD
-
EUG
4h 45mnonstop
United Airlines Logo
2:19 pm - 8:30 pm
EUG
-
ORD
4h 11mnonstop
$329United Airlines
Fri, Aug 14 - Fri, Aug 21
Alaska Airlines Logo
2:20 pm - 9:46 pm
ORD
-
EUG
9h 26m
1 stop
Alaska Airlines Logo
2:29 pm - 11:59 pm
EUG
-
ORD
7h 30m
1 stop
$331Alaska Airlines
Fri, Aug 14 - Fri, Aug 21
Alaska Airlines Logo
2:20 pm - 9:46 pm
ORD
-
EUG
9h 26m
1 stop
Alaska Airlines Logo
2:29 pm - 11:59 pm
EUG
-
ORD
7h 30m
1 stop
$332Alaska Airlines
Wed, Aug 12 - Tue, Aug 18
Southwest Logo
10:30 am - 7:45 pm
MDW
-
BOI
10h 15m
2 stops
Southwest Logo
7:05 am - 5:10 pm
BOI
-
MDW
9h 05m
2 stops
$337Southwest
Fri, Aug 14 - Tue, Aug 18
United Airlines Logo
5:55 am - 12:55 pm
ORD
-
EUG
9h 00m
1 stop
United Airlines Logo
2:19 pm - 8:30 pm
EUG
-
ORD
4h 11mnonstop
$339United Airlines
Mon, Aug 10 - Tue, Aug 11
American Airlines Logo
11:39 am - 2:29 pm
ORD
-
BOI
3h 50mnonstop
American Airlines Logo
1:55 pm - 12:28 am
BOI
-
ORD
9h 33m
1 stop
$340American Airlines
Tue, Jul 28 - Thu, Aug 6
Southwest Logo
6:10 am - 1:25 pm
MDW
-
BOI
8h 15m
1 stop
Southwest Logo
12:10 pm - 4:30 pm
BOI
-
MDW
3h 20mnonstop
$340Southwest
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
5:00 am - 1:03 pm
ORD
-
EUG
10h 03m
1 stop
American Airlines Logo
2:07 pm - 12:28 am
EUG
-
ORD
8h 21m
1 stop
$350American Airlines
Booking Insights

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.

How much is a round-trip flight from Chicago 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 to Oregon departing in August.

What is the cheapest Chicago 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 found in the last 5 days was to Portland, at $231 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 $289.

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

The average price for all round-trip flights from Chicago 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 $456.

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.

No, with an average price for the route of $410, prices are generally cheapest when you fly direct.

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 May, when tickets cost $115 (return) on average. On the other hand, the most expensive months are October and September, when the average cost of round-trip tickets is $817 and $742 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 Tuesday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

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 4 weeks before departure, which saves you about 59% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$127
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 9% 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 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.

Reviews of the 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.
7.9
Alaska AirlinesOverall score based on 12607 reviews
7.1Food
8.1Boarding
8.5Crew
7.0Entertainment
7.8Comfort
Airline reviews

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.

10.0 ExcellentAnonymous, May 2026
ORD - SEA
Read more Alaska Airlines reviews

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.

Thanks for all you do to keep us safe and on time!

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

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

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Long layover in Chicago. Wish that could have been lessened.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

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.

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

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

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 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.

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.