$69 Find Cheap Flights from Oregon to Illinois

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Low seasonJanuary
High seasonMay
Cheapest flight$69
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 10% 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 $224.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Wednesday where round-trip tickets can be as cheap as $468. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $620 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 $356 on average. Morning departures are around 57% 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 $560.

  • 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 $238 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 $238.

  • 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 April and June, when the average cost of round-trip tickets is $845 and $845 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 12m, 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 (82% of total searches to Illinois). The next most popular destinations are St. Louis (14%) and Peoria (2%). Searches for flights to Moline (1%), to Decatur (0%) and to Springfield (0%) 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 9968 reviews
7.1Food
8.2Boarding
8.5Crew
7.1Entertainment
7.9Comfort
Airline reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

8.0 ExcellentAnonymous, Apr 2025PDX - PHX
Read more Alaska Airlines reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

Boarding was quick and easy as always the crew is on their game as always I always have an enjoyable flight so I’m good.

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

It was a short flight so no refreshments or entertainment which was fine.

Flying in both directions across country the gate designated on my boarding pass was wrong. From w to e across the country the passenger next to me coughed the entire way.

Although both planes (flights) had mechanical issue delaying both of my flights, the crew members handled everything with ease. Both flights had the smoothest take off and landing. I opted to upgrade my seat to first class and really lucked out getting the seat at the very front of the plane. Awesome treat to myself. I really enjoyed my flight.

The staff from check-in counter to the flight crew were great. Flight was right on schedule. 10/10

Changed flight from San Fran to Seattle Then with a Delayed takeoff barely made my connection Waited over an hour for luggage 😜

It was good. There was a mistake made in Seattle. Somehow we were bumped out of our seats as if we weren't on the flight anymore. The woman at the gate caught it and announced our name to come up and she fixed it.

I wouldn’t fly with Alaska again if you paid me.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

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

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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.

Paid extra for a “comfy seat” which was anything but!

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

Book cheap flights from Oregon to Illinois

Recent round-trip flight deals

5/29Thu
1 stopSpirit Airlines
13h 48mPDX-ORD
6/3Tue
1 stopSpirit Airlines
6h 55mORD-PDX
$139
5/29Thu
1 stopSpirit Airlines
9h 45mPDX-ORD
6/3Tue
1 stopSpirit Airlines
6h 55mORD-PDX
$150
5/20Tue
1 stopAlaska Airlines
9h 34mBOI-ORD
5/31Sat
1 stopAlaska Airlines
9h 05mORD-BOI
$174
6/10Tue
1 stopDelta
9h 01mBOI-MDW
6/17Tue
1 stopDelta
5h 34mMDW-BOI
$175
5/21Wed
1 stopDelta
6h 45mBOI-ORD
5/30Fri
1 stopDelta
6h 52mORD-BOI
$175
5/20Tue
1 stopUnited Airlines
9h 14mBOI-ORD
5/24Sat
nonstopUnited Airlines
3h 58mORD-BOI
$201
5/19Mon
1 stopAlaska Airlines
7h 41mBOI-ORD
5/28Wed
1 stopAlaska Airlines
7h 05mORD-BOI
$210
9/7Sun
1 stopUnited Airlines
7h 27mBOI-ORD
9/10Wed
nonstopUnited Airlines
3h 46mORD-BOI
$228
6/5Thu
1 stopAmerican Airlines
7h 18mPDX-ORD
6/14Sat
nonstopAmerican Airlines
4h 42mORD-PDX
$252
6/10Tue
nonstopAmerican Airlines
3h 37mBOI-ORD
6/17Tue
nonstopAmerican Airlines
3h 59mORD-BOI
$255

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Recent one-way flight deals

5/17Sat
1 stopSpirit Airlines
13h 48mPDX-ORD
$69
5/29Thu
1 stopSpirit Airlines
9h 45mPDX-ORD
$70
8/13Wed
nonstopUnited Airlines
3h 26mBOI-ORD
$78
7/16Wed
1 stopUnited Airlines
9h 24mBOI-ORD
$83
9/23Tue
1 stopAlaska Airlines
9h 17mBOI-ORD
$87
5/31Sat
1 stopDelta
6h 55mBOI-MDW
$88
5/30Fri
1 stopDelta
7h 50mBOI-ORD
$88
7/15Tue
nonstopAlaska Airlines
4h 04mPDX-ORD
$114
10/8Wed
nonstopAmerican Airlines
3h 37mBOI-ORD
$130
8/18Mon
nonstopAmerican Airlines
3h 40mBOI-ORD
$147

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Last minute flights from Oregon to Illinois

Last minute flight, train and bus deals

5/5Mon
multi-stop
13h 55mPDX-ORD
5/7Wed
nonstop
4h 33mORD-PDX
$209
5/2Fri
multi-stopFrontier
15h 21mPDX-ORD
5/4Sun
multi-stopFrontier
11h 34mORD-PDX
$235
5/5Mon
multi-stopFrontier
13h 55mPDX-ORD
5/12Mon
multi-stopFrontier
9h 17mORD-PDX
$238
5/5Mon
multi-stopAlaska Airlines
5h 59mPDX-ORD
5/10Sat
nonstopAlaska Airlines
4h 33mORD-PDX
$254
5/5Mon
multi-stopAlaska Airlines
8h 40mPDX-ORD
5/13Tue
multi-stopAlaska Airlines
6h 52mORD-PDX
$263
5/5Mon
nonstopUnited Airlines
4h 03mPDX-ORD
5/13Tue
nonstopUnited Airlines
4h 35mORD-PDX
$269
5/5Mon
nonstopUnited Airlines
4h 03mPDX-ORD
5/14Wed
multi-stopUnited Airlines
6h 41mORD-PDX
$299
5/2Fri
multi-stopSpirit Airlines
11h 19mPDX-ORD
5/5Mon
multi-stopSpirit Airlines
7h 56mORD-PDX
$313
5/4Sun
multi-stopSpirit Airlines
9h 32mPDX-ORD
5/6Tue
multi-stopSpirit Airlines
36h 50mORD-PDX
$363
5/2Fri
multi-stopAmerican Airlines
9h 08mPDX-ORD
5/3Sat
multi-stopAmerican Airlines
8h 37mORD-PDX
$575

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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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