$62 Find Cheap Flights from Illinois to Oregon

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Low seasonJanuary
High seasonJuly
Cheapest flight$62
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to Portland

FAQs for booking flights from Illinois to Oregon

  • How does KAYAK find such low prices on flights from Illinois 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 Illinois to Oregon.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Oregon?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois 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 Illinois 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 Illinois 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 Illinois 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 Illinois to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Oregon?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Oregon is Portland Airport (PDX), with an average flight price of $223.

  • What is the cheapest day to fly to Oregon?

    Based on KAYAK data, the cheapest day to fly to Oregon is Wednesday where round-trip tickets can be as cheap as $325. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $394 on average.

  • 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 $271 on average. Morning departures are around 10% 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 $399.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Illinois found in the last 72 hours was to Portland, at $203 round-trip. The most popular route is Chicago Midway Airport (MDW) to Portland (PDX) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $203.

  • What is the cheapest month to fly from Illinois to Oregon?

    The cheapest month for flights from Illinois to Oregon is October, when tickets cost $301 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $705 and $623 respectively.

  • How far in advance should I book a flight from Illinois to Oregon?

    To get a below average price on the flight from Illinois to Oregon, you should book around 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

  • How long is the flight to Oregon?

    An average nonstop flight from Illinois to Oregon takes 9h 05m, covering a distance of 1670 miles. The shortest route is Chicago Midway Airport (MDW) to Boise (BOI) with an average flight time of 3h 35m.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Portland (78% of total searches to Oregon). The next most popular destinations are Boise (10%) and Eugene (4%). Searches for flights to Medford (4%), to Redmond (3%) and to North Bend (1%) are also popular.

Reviews of the top 5 airlines serving from Illinois to Oregon

 
Need help choosing which airline to fly with from Illinois 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
7.1Entertainment
7.1Food
8.5Crew
7.8Comfort
8.1Boarding
Airline reviews

Wonderful staff who honored sleepy overnight travelers and still met needs quietly and quickly!

10.0 ExcellentAnonymous, Jun 2025HNL - PDX
Read more Alaska Airlines reviews

Wonderful staff who honored sleepy overnight travelers and still met needs quietly and quickly!

The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.

1. On time flights. All of our, three separate, flights for three families were late 2. No food on the 5 1/2 hour flight. A substantial snack would have been good. 3. Seat upgrades are expensive 4. No place to move around or stretch on the 5 1/2 hour flight

I like the new adjustable headrest. Unfortunately 2 crying children were in front of us. But it was the first time and not holding Alaska accountable for that. Alaska always seems to have everything in order professional but comfortable.

We had a birthday one day off and almost missed the plane Our fault

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

Thank you still providing bags for vomit. My son had a migraine and needed a bag to vomit in and it was right there behind the seat in front of us. Thank you!

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

It was a quick flight, but coffee would have been great!

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

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

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

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.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

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.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

This was the first time I use Spirit Airlines and was pleasantly surprised. It was a last-minute booking and I was happy to see there was availability on your airline for a price that was affordable. The staff was friendly. The only things I thought were missing, were the ability to recline the seats, although I don’t use that very often, and it would’ve been nice to have power access at the seats to plug in my devices.

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

Not very good because of an almost 3 hour delay for an hour long flight.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Book cheap flights from Illinois to Oregon

Recent round-trip flight deals

8/2Sat
1 stopFrontier
6h 30mORD-PDX
8/4Mon
1 stopFrontier
8h 06mPDX-ORD
$132
8/7Thu
1 stopFrontier
6h 31mORD-PDX
8/11Mon
1 stopFrontier
8h 06mPDX-ORD
$138
7/19Sat
1 stopSpirit Airlines
15h 29mORD-PDX
7/22Tue
1 stopSpirit Airlines
12h 53mPDX-ORD
$174
9/15Mon
1 stopSpirit Airlines
15h 21mORD-BOI
9/19Fri
1 stopSpirit Airlines
13h 20mBOI-ORD
$181
10/25Sat
1 stopAlaska Airlines
8h 10mORD-BOI
10/29Wed
1 stopAlaska Airlines
11h 41mBOI-ORD
$214
9/18Thu
1 stopAlaska Airlines
8h 18mORD-BOI
9/23Tue
1 stopAlaska Airlines
9h 14mBOI-ORD
$224
8/26Tue
1 stopUnited Airlines
7h 19mMLI-PDX
8/31Sun
1 stopUnited Airlines
6h 24mPDX-MLI
$240
8/26Tue
2 stopsUnited Airlines
8h 33mMLI-PDX
8/31Sun
1 stopUnited Airlines
6h 05mPDX-MLI
$245
7/30Wed
1 stopAmerican Airlines
6h 27mMLI-PDX
8/6Wed
1 stopAmerican Airlines
8h 13mPDX-MLI
$251
8/14Thu
nonstopAmerican Airlines
3h 39mORD-BOI
8/21Thu
nonstopAmerican Airlines
3h 33mBOI-ORD
$256

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Recent one-way flight deals

8/2Sat
1 stopFrontier
6h 30mORD-PDX
$62
9/7Sun
1 stopFrontier
7h 49mORD-PDX
$63
7/29Tue
1 stopSpirit Airlines
9h 07mORD-PDX
$79
8/31Sun
nonstopUnited Airlines
4h 25mORD-PDX
$90
9/14Sun
1 stopSpirit Airlines
13h 50mORD-BOI
$90
10/14Tue
1 stopUnited Airlines
10h 03mORD-PDX
$118
7/29Tue
1 stopAlaska Airlines
8h 58mORD-BOI
$125
9/14Sun
nonstopAmerican Airlines
3h 47mORD-BOI
$128
9/18Thu
nonstopAmerican Airlines
3h 47mORD-BOI
$136
8/13Wed
1 stopAlaska Airlines
6h 42mORD-EUG
$139

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Last minute flights from Illinois to Oregon

Last minute flight, train and bus deals

7/5Sat
multi-stopFrontier
6h 30mORD-PDX
7/9Wed
multi-stopFrontier
9h 45mPDX-ORD
$183
7/5Sat
multi-stopFrontier
18h 24mORD-PDX
7/8Tue
multi-stopFrontier
15h 35mPDX-ORD
$192
7/5Sat
multi-stopFrontier
18h 24mORD-PDX
7/11Fri
multi-stopFrontier
28h 20mPDX-ORD
$195
7/4Fri
nonstopAmerican Airlines
3h 56mORD-BOI
7/7Mon
nonstopAmerican Airlines
3h 37mBOI-ORD
$316
7/4Fri
nonstopAmerican Airlines
3h 56mORD-BOI
7/7Mon
multi-stopAmerican Airlines
7h 01mBOI-ORD
$326
7/4Fri
nonstopUnited Airlines
4h 07mORD-BOI
7/7Mon
multi-stopUnited Airlines
10h 00mBOI-ORD
$386
7/4Fri
nonstopUnited Airlines
3h 58mORD-BOI
7/6Sun
nonstopUnited Airlines
3h 40mBOI-ORD
$396
7/3Thu
multi-stopAlaska Airlines
10h 52mORD-MFR
7/5Sat
multi-stopAlaska Airlines
5h 53mMFR-ORD
$489
7/2Wed
multi-stopAlaska Airlines
8h 13mORD-MFR
7/4Fri
multi-stopAlaska Airlines
22h 27mMFR-ORD
$494
7/3Thu
multi-stopSpirit Airlines
23h 29mORD-BOI
7/7Mon
multi-stopSpirit Airlines
20h 08mBOI-ORD
$990

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Everything you need to know for your flight to Oregon

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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