$89 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 6/3. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$240
Eugene
Eugene1 stop$177
Redmond
Redmond1 stop$357
Medford
Medford2 stops$318
Boise
Boise1 stop$236
Portland
Portlandnonstop$240
Eugene
Eugene1 stop$177
Redmond
Redmond1 stop$357
Medford
Medford2 stops$318
Boise
Boise1 stop$236

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 28 - Tue, Jun 2
Delta Logo
7:12 am - 12:55 pm
ORD
-
EUG
7h 43m
1 stop
Delta Logo
12:35 pm - 11:55 pm
EUG
-
ORD
9h 20m
1 stop
$177Delta
Thu, May 28 - Tue, Jun 2
Delta Logo
7:12 am - 12:55 pm
ORD
-
EUG
7h 43m
1 stop
Delta Logo
6:15 am - 9:50 pm
EUG
-
ORD
13h 35m
2 stops
$182Delta
Thu, May 28 - Tue, Jun 2
Southwest Logo
5:15 pm - 10:45 pm
MDW
-
EUG
7h 30m
1 stop
Southwest Logo
11:20 am - 8:40 pm
EUG
-
MDW
7h 20m
1 stop
$207Southwest
Tue, Jul 14 - Mon, Jul 20
Southwest Logo
5:30 am - 1:00 pm
MDW
-
EUG
9h 30m
2 stops
Southwest Logo
6:40 pm - 5:00 am
EUG
-
MDW
8h 20m
1 stop
$212Southwest
Wed, May 13 - Sun, May 17
Frontier Logo
9:37 pm - 12:27 pm
ORD
-
BOI
15h 50m
1 stop
Frontier Logo
1:22 pm - 8:32 pm
BOI
-
ORD
6h 10m
1 stop
$236Frontier
Wed, Aug 19 - Wed, Aug 26
Alaska Airlines Logo
7:00 am - 9:28 am
ORD
-
PDX
4h 28mnonstop
Alaska Airlines Logo
2:00 pm - 11:57 pm
PDX
-
ORD
7h 57m
1 stop
$240Alaska Airlines
Wed, May 13 - Mon, May 18
Frontier Logo
8:56 pm - 11:50 am
ORD
-
PDX
16h 54m
1 stop
Frontier Logo
5:31 pm - 6:39 am
PDX
-
ORD
11h 08m
1 stop
$241Frontier
Tue, May 12 - Sat, May 16
United Airlines Logo
8:00 pm - 10:35 pm
ORD
-
PDX
4h 35mnonstop
United Airlines Logo
7:45 pm - 5:40 am
PDX
-
ORD
7h 55m
1 stop
$245United Airlines
Sat, Aug 22 - Wed, Aug 26
Alaska Airlines Logo
7:00 am - 9:28 am
ORD
-
PDX
4h 28mnonstop
Alaska Airlines Logo
5:35 pm - 11:41 pm
PDX
-
ORD
4h 06mnonstop
$250Alaska Airlines
Sat, Jul 18 - Sat, Jul 25
United Airlines Logo
6:10 pm - 11:37 pm
ORD
-
RDM
7h 27m
1 stop
United Airlines Logo
7:39 pm - 5:57 am
RDM
-
ORD
8h 18m
1 stop
$359United 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 72 hours was to Portland, at $283 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 $283.

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 $321 on average. Morning departures are around 5% 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 $462.

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 $349, 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 $427 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 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 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$89
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago O'Hare Airport to Eugene

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
SouthwestOverall score based on 4330 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

onboard snack was pretzels, but the FA was super nice when my neighbor asked for cookies instead and also brought some for me. :)

On time. .breakfast was especially good. First class service was special

Had to buy a snack box as I am gluten free. They should be free in extra comfort. Food they provided was awful. Not enough water stops.

Tight hot cramped seating. Gate change plus a board and de plane request with two hour delay

We treated ourselves to first class and were underwhelmed by the experience. No screen for entertainment. Food was not great...only one or two options, small portions, dry. We won't waste our money upgrading again. Good news was we made it to PDX safe and sound. Crew was attentive.

The flight would have been very good , if not dor the constantly screaming baby in the row behind me. Is there a way to isolate people traveling with infants? This is not the first time this has happened to me.

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

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

it was good except the too big men in my personal space.

We were on the ground for over 2hrs Flt scheduled to leave at 5:40pm, actual departure was at 9:00pm. Around 8:00pm we were offered an option to deplane,some did while others stayed.

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

The Honolulu Hub needs 2 to 3 times the amount of things to do as well as shuttles that transport to/from gates and terminals. Arriving from OCONUS locations; transferring to CONUS locations its a miserable experience. Fetching and re-checking bags, then returning to a gate across the airport take longer than any other large airport. If youre confused by what I mean, the process goes like this: Disembark plane Walk a mile to the main terminal Walk half a mile to baggage claim Wait 40 minutes for baggage Walk a mile to re-check-in baggage Wait 20 minutes for checking in those bags Fo back through the wrong TSA line because the signage is poor Almost miss the connecting flight because your gate is across the airport.

The checking was disaster, the crew wasn't behave well. It took us two hours to check in, after that thr line at the TSA was long, we barely make the flight. Bad airline

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

The crew were exceptionally nice and accommodating. My wife was tired after the flight from Haneda, Tokyo. They let her sleep and served her dinner later after she woke up, before we landed in PDX.

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.

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.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

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.

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.