$74 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 9/30. 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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Cheap Flights from Chicago to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$203
Eugene
Eugene1 stop$209
Redmond
Redmond1 stop$233
Medford
Medford1 stop$245
Boise
Boise1 stop$157
Portland
Portland1 stop$203
Eugene
Eugene1 stop$209
Redmond
Redmond1 stop$233
Medford
Medford1 stop$245
Boise
Boise1 stop$157

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

Tue, Mar 3 - Wed, Mar 4
Delta Logo
9:20 am - 2:09 pmMDW-BOI
5h 49m1 stop
Delta Logo
5:40 am - 1:08 pmBOI-MDW
6h 28m1 stop
$157Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
7:30 am - 4:26 pmORD-BOI
9h 56m1 stop
Delta Logo
2:00 pm - 11:44 pmBOI-ORD
8h 44m1 stop
$157Delta
Find Deal
Wed, Nov 12 - Sat, Nov 15
Southwest Logo
5:25 am - 2:05 pmMDW-BOI
9h 40m1 stop
Southwest Logo
5:00 am - 11:45 amBOI-MDW
5h 45m1 stop
$160Southwest
Find Deal
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
9:45 am - 12:40 pmORD-BOI
3h 55mnonstop
American Airlines Logo
1:20 pm - 5:55 pmBOI-ORD
3h 35mnonstop
$163American Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
6:00 am - 10:40 amMDW-BOI
5h 40m1 stop
Southwest Logo
1:30 pm - 9:50 pmBOI-MDW
7h 20m1 stop
$163Southwest
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
7:45 am - 4:20 pmORD-BOI
9h 35m1 stop
Alaska Airlines Logo
6:00 am - 1:04 pmBOI-ORD
6h 04m1 stop
$178Alaska Airlines
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Fri, Oct 3 - Sun, Oct 5
United Airlines Logo
4:05 pm - 6:47 pmORD-BOI
3h 42mnonstop
United Airlines Logo
3:10 pm - 7:40 pmBOI-ORD
3h 30mnonstop
$179United Airlines
Find Deal
Wed, Nov 12 - Sat, Nov 15
United Airlines Logo
4:17 pm - 11:28 pmORD-BOI
8h 11m1 stop
United Airlines Logo
12:35 pm - 5:10 pmBOI-ORD
3h 35mnonstop
$201United Airlines
Find Deal
Sat, Jan 24 - Mon, Jan 26
Alaska Airlines Logo
2:05 pm - 4:39 pmORD-PDX
4h 34mnonstop
Alaska Airlines Logo
7:00 am - 1:04 pmPDX-ORD
4h 04mnonstop
$207Alaska Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
9:56 am - 12:46 pmORD-BOI
3h 50mnonstop
American Airlines Logo
1:40 pm - 6:27 pmBOI-ORD
3h 47mnonstop
$207American Airlines
Find Deal
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 $136 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 $179.

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 $298, 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 September, when tickets cost $271 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $418 and $414 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 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 4 weeks before departure, which saves you about 39% 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$74
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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.

  • 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 $324 on average. Morning departures are around 12% 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 $444.

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 10000 reviews
8.1Boarding
7.1Food
7.8Comfort
7.0Entertainment
8.5Crew
Airline reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

10.0 ExcellentAnonymous, Sep 2025ONT - PDX
Read more Alaska Airlines reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

Planes were on time. Pilot kept everyone updated. Crew was friendly and helpful

Flight was switched to a different airline. Caused scheduling issues. Flight delayed an hour, but arrived only 20 minutes late thanks to tail winds.

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

You no longer give receipts for baggage at the counter. And it is next to impossible to get it on your webpage. Spent 20 min trying and gave up... I need receipt to submit for reimbursement and don't have time to waste on your poor webpage Disappointing .....

The flight attendants were unkempt and show no customer service skills. They avoided eye contact. There were no smiles and they were dismissive and snarky.

Complete flight rebooked and 6 hours delayed. Zero accountability from the airline or Kayak for the issues and I’m injured which is why I opted to pay more to fly than drive because it’s painful to sit or stand too long. What was supposed to be a 3ish hour travel day turned into a 9 hour excruciatingly painful experience that has left me in worse pain than when I initially started.

It was a good flight, short so there was no food or water service

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 🤙

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.

All was good and they were able to seat my travel companion next to me. Thank you.

Like the ample leg room. May as well not bother with snacks if it's only a two ounce bag of pretzels. Didn't use the entertainment option. Was there one?

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Kayak sold me a ticket after check in time. Could not check in. Could not get on flight.

Love you guys are so friendly and kind and wonderful

Agents talk too fast over intercom. I know it’s memorized and we’ve all heard it before. Just slow down a little. Stop charging for checked bags. I was pleased to get my bags promptly at each end of my flight.

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

It was clean and the crew was great. I wish the chairs could recline just a little more and you would provide small pillows for people with bad backs. My back is fused and a little support would be great.

I accidentally made this purchase and they wouldn’t refund me even though I called immediately to cancel it.

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.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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.

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.

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

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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