$90 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 9/17. 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$182
Eugene
Eugene1 stop$278
Redmond
Redmond1 stop$278
Medford
Medford1 stop$278
Boise
Boise2 stops$220
Portland
Portland1 stop$182
Eugene
Eugene1 stop$278
Redmond
Redmond1 stop$278
Medford
Medford1 stop$278
Boise
Boise2 stops$220

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, Sep 11 - Sun, Sep 14
Frontier Logo
6:00 am - 12:12 amORD-PDX
20h 12m1 stop
Frontier Logo
10:17 am - 10:40 pmPDX-ORD
10h 23m1 stop
$182Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
Frontier Logo
6:00 am - 12:12 amORD-PDX
20h 12m1 stop
Frontier Logo
6:05 am - 11:59 pmPDX-ORD
15h 54m1 stop
$184Frontier
Find Deal
Fri, Oct 31 - Sat, Nov 8
Alaska Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
Alaska Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
$203Alaska Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
Southwest Logo
3:45 pm - 6:05 pmMDW-PDX
4h 20mnonstop
Southwest Logo
10:15 am - 9:30 pmPDX-MDW
9h 15m1 stop
$213Southwest
Find Deal
Fri, Sep 5 - Thu, Sep 25
United Airlines Logo
1:05 pm - 3:25 pmORD-PDX
4h 20mnonstop
United Airlines Logo
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
$214United Airlines
Find Deal
Fri, Oct 31 - Thu, Nov 6
Alaska Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
Alaska Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
$218Alaska Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
Southwest Logo
5:15 am - 9:50 amMDW-PDX
6h 35m1 stop
Southwest Logo
2:05 pm - 10:35 pmPDX-MDW
6h 30m1 stop
$222Southwest
Find Deal
Wed, Oct 29 - Sat, Nov 1
United Airlines Logo
4:05 pm - 6:40 pmORD-PDX
4h 35mnonstop
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
$227United Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
American Airlines Logo
9:56 am - 12:46 pmORD-BOI
3h 50mnonstop
American Airlines Logo
1:26 pm - 6:14 pmBOI-ORD
3h 48mnonstop
$255American Airlines
Find Deal
Sat, Oct 4 - Tue, Oct 7
American Airlines Logo
9:40 am - 12:27 pmORD-BOI
3h 47mnonstop
American Airlines Logo
1:26 pm - 6:14 pmBOI-ORD
3h 48mnonstop
$264American 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.

How much is a round-trip flight from Chicago to Oregon?

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 $183.

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 $656, 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 December and March, when the average cost of round-trip tickets is $422 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 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 38% 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$90
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 $317 on average. Morning departures are around 13% 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 $435.

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

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

10.0 ExcellentAnonymous, Aug 2025BIL - PDX
Read more Alaska Airlines reviews

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

Plane was delayed getting boarded and then again delayed in take-off order. Alaska Airlines must have very little clout at JFK so they don't get priority treatment. All the delays meant we missed the last flight from Portland to Eugene. Alaska did give us hotel voucher for the night...but sent us to a downtown Portland hotel rather than to a nearby airport motel which made for a longer ride at night and then again in the morning. Just made an already long, late night even longer. Hotel was an old outdated Hilton in a slightly seedy part of town. Alaska gave us Lyft vouchers for getting to the hotel, but the return voucher for getting back to the airport in the morning didn't work.

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.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Attendants seemed un-engaged and indifferent when asked for assistance.

Overall it was a good flight. The thing I most appreciated was that you eliminated plastic cups and water bottles and stir sticks and had paper cups, wood stir sticks and cans. Plus, I saw that the airline staff were actually keeping the used paper cups separate and unfolding the used cardboard meal boxes and keeping those items separate from the trash. Good for them! This makes me want to support Alaska Airlines and fly Alaska again. Thank for taking this step in working to reduce single use plastics! Kudos!

It was pretty good except there was no food, which was understandable because it was a short flight but I would have liked to at least have a snack; otherwise it was great. Staff/crew, great. Thank you

I was on Alaska and its backup airline. I was scheduled for wheelchair service but ON ONE SHOWED UP. When I asked, desk attendant said they didn’t have any.

As noted above, getting on to the plane was rushed and upsetting since no boarding passes were available to me prior to boarding. Others were in line waiting as well. The flight and experience itself was fine. Very large plane. Two seats near windows; 4 seats in the middle aisles. Good leg room though and comfortable seats.

The trip was fine, however once we reached Seattle, our next flight only had an hour turn-around time and we had to cross the entire Seattle airport, taking three shuttles. Once there, Alaska/Hawaiian Air had still not issued my boarding passes to us and we had to wait at the counter for them. Boarding was already started and at the second to last seating level when we finally got our boarding passes. This was a bit nuts.

I am disappointed with Alaska. They are just like the cheapo airlines, nickle and dimeing us for everything. We now have to pay extra to pick our seats? Really?

I could not use my Hawaiian airlines confirmation number to check in. I figured out on my own that I had to use Alaska airlines confirmation number to check in on the Alaska airlines site. I called Hawaiian airlines and they told me that they could not help me.

Alaska Airlines crew had the empty two people seats but they lied to us and said they can adjust us , so we have to seat apart

Ok but why they need to sell the ear buds?

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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