$85 Find Cheap Flights from Oregon to Illinois

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Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$85
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Portland to Chicago O'Hare Airport

FAQs for booking flights from Oregon to Illinois

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

    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 Oregon to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oregon to Illinois 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 Oregon to Illinois?

    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 Oregon to Illinois 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 Oregon to Illinois?

    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 Oregon to Illinois 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 Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $241.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Friday where round-trip tickets can be as cheap as $458. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $587 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $311 on average. Morning departures are around 70% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $529.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Oregon found in the last 72 hours was to Chicago Midway Airport, at $236 round-trip. The most popular route is Portland (PDX) to Chicago Midway Airport (MDW) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $236.

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

    The cheapest month for flights from Oregon to Illinois is February, when tickets cost $304 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $919 and $748 respectively.

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

    To get a below average price on the flight from Oregon to Illinois, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

  • How long is the flight to Illinois?

    An average nonstop flight from Oregon to Illinois takes 10h 05m, covering a distance of 1649 miles. The shortest route is Boise (BOI) to Chicago Midway Airport (MDW) with an average flight time of 3h 20m.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (86% of total searches to Illinois). The next most popular destinations are St. Louis (9%) and Peoria (2%). Searches for flights to Moline (1%), to Bloomington (1%) and to Decatur (1%) are also popular.

Top 5 airlines serving from Oregon to Illinois

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

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

10.0 Excellentmarlene, Jun 2025PDX - SMF
Read more Alaska Airlines reviews

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

No WiFi available. It was too late to order food also. Guy next to me was huge (not fat) so had his shoulder & thigh next to me the whole way. Plane was delayed leaving PDX due to 8 other planes waiting. Not my best Alaska airlines flight.

Everyone was very helpful. My only critique was the very hard landing in Seattle. We felt the G force.

Check in, they should have told me that upon arrival i needed to exit the secure area and re-check in with Eva Air. I wasn't sure what to do upon arrival at S.F.

The direct service from Logan to PDX made travel so easy, I really appreciate this route. Pilots were very communicative with passengers about conditions and expectations. Everyone on staff was pleasant and helpful. Boarding was easy and efficient.

Flight last minute delayed 2 hours for crew calling out sick

Husband was new to the wheelchair accommodations this trip. What a blessing that was. All employees were helpful and customer service was excellent

Way too warm for that length of flight!! If the pretzel bag gets any smaller, there won't even be any pretzels to eat!! Crew didn't talk. $99 just for an aisle seat is ludicrous!! Probably won't fly Alaska again.

Seats are still too crowded and uncomfortable on long flights like this cross country one.

Laney was very helpful. I am computer illiterate. She helped me obtain a boarding pass and preferred seat. She was warm, friendly, helpful, and smiled. I was impressed.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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 liked that the flight was nonstop from ORD to CIU for $200 round trip.

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!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

Book cheap flights from Oregon to Illinois

Recent round-trip flight deals

8/21Thu
1 stop
7h 08mPDX-ORD
8/30Sat
1 stop
17h 39mORD-PDX
$171
7/9Wed
1 stopSpirit Airlines
12h 53mPDX-ORD
7/14Mon
1 stopSpirit Airlines
9h 07mORD-PDX
$174
9/6Sat
nonstopAlaska Airlines
4h 09mPDX-ORD
9/10Wed
nonstopAlaska Airlines
4h 29mORD-PDX
$181
9/6Sat
nonstopAlaska Airlines
4h 09mPDX-ORD
9/9Tue
1 stopAlaska Airlines
6h 24mORD-PDX
$191
10/3Fri
1 stopDelta
8h 04mBOI-ORD
10/11Sat
1 stopDelta
9h 59mORD-BOI
$195
7/12Sat
1 stopDelta
6h 26mBOI-MDW
7/19Sat
2 stopsDelta
8h 40mMDW-BOI
$200
7/1Tue
nonstopUnited Airlines
4h 01mPDX-ORD
7/3Thu
nonstopUnited Airlines
4h 33mORD-PDX
$234
7/9Wed
1 stopUnited Airlines
7h 11mEUG-ORD
7/17Thu
1 stopUnited Airlines
7h 54mORD-EUG
$239
9/6Sat
nonstopAmerican Airlines
3h 38mBOI-ORD
9/13Sat
nonstopAmerican Airlines
3h 47mORD-BOI
$255
7/30Wed
nonstopAmerican Airlines
3h 56mPDX-ORD
8/2Sat
nonstopAmerican Airlines
4h 39mORD-PDX
$272

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Recent one-way flight deals

7/1Tue
1 stopSpirit Airlines
9h 33mPDX-ORD
$85
8/31Sun
nonstopUnited Airlines
4h 08mPDX-ORD
$90
8/16Sat
1 stopDelta
6h 33mBOI-MDW
$91
9/2Tue
1 stopDelta
6h 31mBOI-ORD
$91
9/3Wed
nonstopSouthwest
4h 00mPDX-MDW
$91
9/23Tue
1 stopSouthwest
11h 10mBOI-MDW
$96
8/29Fri
nonstopAlaska Airlines
4h 00mPDX-ORD
$104
8/26Tue
1 stopAlaska Airlines
8h 24mEUG-ORD
$107
7/16Wed
1 stopAmerican Airlines
6h 58mRDM-ORD
$130
9/16Tue
1 stopAmerican Airlines
13h 46mPDX-STL
$139

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Last minute flights from Oregon to Illinois

Last minute flight, train and bus deals

6/17Tue
multi-stopSpirit Airlines
14h 11mPDX-ORD
6/23Mon
multi-stopSpirit Airlines
15h 02mORD-PDX
$284
6/13Fri
multi-stopDelta
5h 12mBOI-ORD
6/16Mon
multi-stopDelta
6h 44mORD-BOI
$303
6/13Fri
nonstopAmerican Airlines
3h 37mBOI-ORD
6/16Mon
nonstopAmerican Airlines
3h 59mORD-BOI
$377
6/13Fri
multi-stopAmerican Airlines
7h 08mBOI-ORD
6/16Mon
nonstopAmerican Airlines
3h 59mORD-BOI
$387
6/13Fri
nonstopSouthwest
3h 20mBOI-MDW
6/16Mon
multi-stopSouthwest
7h 50mMDW-BOI
$387
6/13Fri
multi-stopSouthwest
5h 45mBOI-MDW
6/16Mon
multi-stopSouthwest
9h 10mMDW-BOI
$442
6/14Sat
multi-stopAlaska Airlines
8h 39mPDX-STL
7/5Sat
multi-stopAlaska Airlines
12h 48mSTL-PDX
$499
6/14Sat
multi-stopAlaska Airlines
18h 51mPDX-STL
7/5Sat
multi-stopAlaska Airlines
12h 47mSTL-PDX
$539
6/14Sat
multi-stopUnited Airlines
8h 57mEUG-ORD
7/20Sun
multi-stopUnited Airlines
7h 10mORD-EUG
$571
6/14Sat
multi-stopUnited Airlines
6h 30mPDX-STL
6/21Sat
multi-stopUnited Airlines
6h 42mSTL-PDX
$588

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Everything you need to know for your flight to Illinois

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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