$104 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 4/4. 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

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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Cheap Flights from Chicago to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$201
Eugene
Eugene1 stop$217
Redmond
Redmond1 stop$265
Medford
Medford2 stops$270
Boise
Boisenonstop$222
Portland
Portland1 stop$201
Eugene
Eugene1 stop$217
Redmond
Redmond1 stop$265
Medford
Medford2 stops$270
Boise
Boisenonstop$222

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, May 14 - Mon, May 18
Frontier Logo
7:21 pm - 11:57 am
ORD
-
PDX
18h 36m
1 stop
Frontier Logo
9:53 am - 5:50 am
PDX
-
ORD
17h 57m
1 stop
$201Frontier
Mon, Apr 13 - Fri, Apr 24
Frontier Logo
2:29 pm - 1:02 pm
ORD
-
PDX
24h 33m
1 stop
Frontier Logo
9:54 am - 5:50 am
PDX
-
ORD
17h 56m
1 stop
$203Frontier
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
9:44 pm - 12:15 am
ORD
-
PDX
4h 31mnonstop
American Airlines Logo
3:16 pm - 9:34 pm
PDX
-
ORD
4h 18mnonstop
$207American Airlines
Sat, Apr 4 - Sat, Apr 11
United Airlines Logo
9:08 am - 11:44 am
ORD
-
PDX
4h 36mnonstop
United Airlines Logo
12:50 pm - 10:58 pm
PDX
-
ORD
8h 08m
1 stop
$217United Airlines
Sun, Apr 12 - Thu, Apr 16
Southwest Logo
6:00 am - 10:15 am
MDW
-
EUG
6h 15m
1 stop
Southwest Logo
2:50 pm - 11:40 pm
EUG
-
MDW
6h 50m
1 stop
$217Southwest
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
7:00 am - 9:24 am
ORD
-
PDX
4h 24mnonstop
American Airlines Logo
1:20 pm - 7:18 pm
PDX
-
ORD
3h 58mnonstop
$220American Airlines
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
12:35 pm - 10:00 pm
MDW
-
EUG
11h 25m
1 stop
Southwest Logo
5:20 pm - 5:00 am
EUG
-
MDW
9h 40m
1 stop
$222Southwest
Wed, Apr 22 - Tue, Apr 28
Alaska Airlines Logo
3:52 pm - 10:54 pm
ORD
-
EUG
9h 02m
1 stop
Alaska Airlines Logo
1:23 pm - 11:59 pm
EUG
-
ORD
8h 36m
1 stop
$227Alaska Airlines
Wed, Apr 22 - Tue, Apr 28
Alaska Airlines Logo
8:00 am - 1:52 pm
ORD
-
BOI
6h 52m
1 stop
Alaska Airlines Logo
6:00 am - 4:56 pm
BOI
-
ORD
9h 56m
1 stop
$249Alaska Airlines
Tue, Apr 14 - Wed, Apr 22
United Airlines Logo
6:25 am - 11:55 am
ORD
-
RDM
7h 30m
1 stop
United Airlines Logo
1:55 pm - 12:59 am
RDM
-
ORD
9h 04m
1 stop
$272United 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.

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 72 hours was to Portland, at $176 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 $176.

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 $302 on average. Morning departures are around 17% 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 $448.

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 $301, 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 January, when tickets cost $257 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $428 and $385 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 Mondays 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 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 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$104
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 8% 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.
8.0
Alaska AirlinesOverall score based on 12018 reviews
7.0Entertainment
7.8Comfort
7.1Food
8.1Boarding
8.5Crew
Airline reviews

Not bad. Due to not buying a seat, on the way back, my seat was not assigned till 2 hrs before the flight left. Got me worried I wouldn’t have a seat.

6.0 GoodAnonymous, Mar 2026
ONT - PDX
Read more Alaska Airlines reviews

Not bad. Due to not buying a seat, on the way back, my seat was not assigned till 2 hrs before the flight left. Got me worried I wouldn’t have a seat.

It was not a good experience, the flight was delayed 3 hours, the gate staff were super pushy to get bags checked claiming it was a full flight, there were about a dozen open seats from what I could tell. The intercom from the pilot seemed to be broken, it sounded like the pilot was speaking with a mouth full of marbles.

There was an issue with the plane and it was late getting in. This caused me to miss my connecting flight from PDX to BOI. I had to ask if they would provide me with a food voucher and they did but didn’t seem to concerned about my delay.

The flight was delayed by 2 hours for “routine maintenance”and because of that I arrived much later iso my Uber ride home was $100 when it’s normally $50.

More or less, this seemed like a mismanaged group of great people who would crush at this job, if only they were given the resources to do so.

Plane destination at the Gates were mixed up at Spokane airport. Text from website didn't match rithet

It was fine. I upgraded to premium economy & lived the extra legroom. Unfortunately, I was seated next to a man who sniffled A LOT during the flight and had his earphones on so loud that I could hear the music sitting next to him!

I enjoyed the feet space in comparison to other airlines. The snacks were also better, great service and the pilot greeted and said hi which made me feel safer.

Well the seats were very tight but the plane was very clean, the attendance great and good entertainment. Maybe they had it, but I wanted a map on the app. Thanks

had to be rerouted due to a medical emergency onboard. Alaska crew treated the patient with utmost respect and continued to keep the passengers updated the entire way through, which I appreciate. But it took 4 hours from landing until we were able to be airborne again, causing us to not get into SFO until ~2 am. I understand it was a tough situation for everyone, but that was an indecent wait.

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

Alaska was fine as usual. My frustration came with accessing boarding passes. On the first trip, I could only get one to print ans took a picture of the second one. On our return trip, the system was down? Friends who booked directly with Alaska had theirs process. I even tried the 800 number and had others try it too. It said something in Spanish and hung up. The agent at the airport succeeded.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

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.