$128 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 8/31. 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
Portlandnonstop$309
Eugene
Eugene1 stop$309
Redmond
Redmond1 stop$369
Medford
Medford1 stop$357
Boise
Boise1 stop$339
Portland
Portlandnonstop$309
Eugene
Eugene1 stop$309
Redmond
Redmond1 stop$369
Medford
Medford1 stop$357
Boise
Boise1 stop$339

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

Mon, Jun 29 - Tue, Jul 7
United Airlines Logo
6:10 am - 12:01 pm
ORD
-
EUG
7h 51m
1 stop
United Airlines Logo
12:50 pm - 7:00 pm
EUG
-
ORD
4h 10mnonstop
$309United Airlines
Wed, Jul 22 - Tue, Jul 28
Alaska Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Alaska Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
$309Alaska Airlines
Wed, Jul 15 - Sun, Jul 19
Alaska Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Alaska Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
$310Alaska Airlines
Sat, Jul 4 - Thu, Jul 9
United Airlines Logo
9:00 am - 11:44 am
ORD
-
EUG
4h 44mnonstop
United Airlines Logo
12:50 pm - 7:00 pm
EUG
-
ORD
4h 10mnonstop
$314United Airlines
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$315Southwest
Sat, Jul 11 - Sat, Jul 18
American Airlines Logo
10:15 pm - 12:50 am
ORD
-
PDX
4h 35mnonstop
American Airlines Logo
6:07 am - 12:17 pm
PDX
-
ORD
4h 10mnonstop
$316American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
8:20 am - 10:49 am
ORD
-
PDX
4h 29mnonstop
American Airlines Logo
11:46 am - 5:52 pm
PDX
-
ORD
4h 06mnonstop
$317American Airlines
Tue, Jul 28 - Tue, Aug 4
Southwest Logo
9:10 pm - 11:35 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$320Southwest
Sat, Sep 26 - Fri, Oct 2
Delta Logo
1:47 pm - 8:16 pm
MDW
-
PDX
8h 29m
1 stop
Delta Logo
12:20 am - 8:50 am
PDX
-
MDW
6h 30m
1 stop
$335Delta
Thu, Jul 2 - Thu, Jul 9
Delta Logo
7:37 pm - 11:58 pm
ORD
-
EUG
6h 21m
1 stop
Delta Logo
6:15 am - 6:57 pm
EUG
-
ORD
10h 42m
2 stops
$339Delta
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 July.

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 $250 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 $305.

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 $329 on average. Morning departures are around 7% 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 $467.

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 $393, 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 $909 and $756 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 55% 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$128
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 5% 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
SouthwestOverall score based on 4258 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

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.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Couldn’t order food for the family because all the good food was unavailable. We opted for bringing something on with us. I also didn’t like that I had to have T-mobile for online movies. Stupid.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

The flight crew home was so, so friendly and HILARIOUS. I’ll keep flying Alaska like I have for the last 30+ years!

Deboarding the plane was chaos. The passengers in the back of the plane started deplaning before the passengers in the middle of the plane could even retrieve their overhead bags. The staff of the plane did nothing to help.

Enforce the one bag rule for carry ons. Don't allow people to have 2 and 3 carry ons. Make baggage gets loaded onto the correct plane. My bag didn't get put onto my last flight so I didn't get it until the next day.

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

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

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.

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.

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 airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

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.

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.