$80 Find Cheap Flights from Oregon to Illinois

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Low seasonJanuary
High seasonAugust
Cheapest flight$80
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Boise 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 Midway Airport (MDW), with an average flight price of $239.

  • 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 $457. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $572 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 $310 on average. Morning departures are around 67% 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 $518.

  • 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 $188 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 $188.

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

    The cheapest month for flights from Oregon to Illinois is August, when tickets cost $282 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $477 and $475 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 18m, 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 (91% of total searches to Illinois). The next most popular destinations are St. Louis (6%) and Peoria (1%). Searches for flights to Moline (1%), to Bloomington (0%) and to Decatur (0%) are also popular.

Reviews of the 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
7.1Food
7.1Entertainment
8.5Crew
7.8Comfort
8.1Boarding
Airline reviews

Friendly staff, everything went smoothly. Gluten free snacks would would be the cherry on top!

10.0 ExcellentAnonymous, Jul 2025RDM - PDX
Read more Alaska Airlines reviews

Friendly staff, everything went smoothly. Gluten free snacks would would be the cherry on top!

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

I'm a platinum member with American Airlines, however, my ticket did not display status and thus I did not board with an early group. I traveled with my two daughters and we were given a row of seats that did not recline. Not the treatment I would have expected for a platinum customer. The flight was also a bit late leaving Portland. Also on my flight to Portland we were not given premium seats. In fact, we were in the last row of the aircraft.

It was fine. 2 hour delay due to mechanical issue. I understand issues will occur, just wish instead of Capt repeatedly telling us we will be getting off the ground “momentarily” they would just be honest and either say they have no idea-or it’s going to be a few hours! All in all FAs are usually pretty nice :)

I was at risk of not getting on the flight, as when I presented my boarding pass at the gate, it showed me as not having checked in. I was sent to the desk as the last of the other passengers boarded. The agent there said he could see that I had done all of my part and allowed times recommended, but it showed me as not checked in and he couldn't figure out how to correct it. He actually asked them to hold the flight as he struggled with it. He called for support, someone corrected it, and he printed boarding passes for both flights to reduce further issues. I did get on, and needed to ask someone to exit my seat.

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

5 hour delay from Portland to Newark. Boarded and then were told we had to get off and wait five hours for flight. No food vouchers or any other compensation because they said it was an air traffic control issue. Plane is bare minimum like a discount airline. They have free entertainment but you have to get to it on your own device no screens in the seats

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

Very good. Gate personnel were excellent flight attendants were also able to change my seat at the last minute everyone, courteous, polite, and.

It was horrible. Last minute gate change, delays, more delays and then we had to wait for a stweardess to onboard. No explanation for the wait. No apologies. We got to RDM way past schedule @ 1:30 am!!!! Stressful and exhausting. We'd avoid flying Alaska ever again.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

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.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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 flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

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

Book cheap flights from Oregon to Illinois

Recent round-trip flight deals

8/30Sat
nonstopAmerican Airlines
3h 33mBOI-ORD
9/2Tue
nonstopAmerican Airlines
3h 39mORD-BOI
$159
8/23Sat
1 stopFrontier
15h 12mPDX-ORD
8/25Mon
1 stopFrontier
7h 23mORD-PDX
$159
9/24Wed
1 stopAlaska Airlines
6h 29mBOI-ORD
9/30Tue
1 stopAlaska Airlines
8h 30mORD-BOI
$178
8/30Sat
1 stopSouthwest
6h 55mBOI-MDW
9/6Sat
1 stopSouthwest
8h 40mMDW-BOI
$179
9/26Fri
1 stopSpirit Airlines
13h 20mBOI-ORD
9/29Mon
1 stopSpirit Airlines
15h 21mORD-BOI
$182
9/17Wed
1 stopSpirit Airlines
14h 42mPDX-ORD
9/24Wed
1 stopSpirit Airlines
12h 04mORD-PDX
$183
9/3Wed
1 stopSouthwest
6h 15mBOI-MDW
9/5Fri
nonstopSouthwest
3h 45mMDW-BOI
$185
9/24Wed
1 stopAlaska Airlines
6h 29mBOI-ORD
9/29Mon
1 stopAlaska Airlines
9h 40mORD-BOI
$188
8/30Sat
nonstopUnited Airlines
4h 10mPDX-ORD
9/3Wed
nonstopUnited Airlines
4h 36mORD-PDX
$203
8/23Sat
1 stopUnited Airlines
7h 15mEUG-ORD
8/28Thu
1 stopUnited Airlines
8h 20mORD-EUG
$309

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Recent one-way flight deals

8/20Wed
nonstopAmerican Airlines
3h 33mBOI-ORD
$80
8/18Mon
1 stopSpirit Airlines
9h 44mBOI-ORD
$81
8/30Sat
nonstopUnited Airlines
4h 01mPDX-ORD
$90
8/20Wed
1 stopSouthwest
6h 15mBOI-MDW
$90
8/30Sat
nonstopSouthwest
4h 00mPDX-MDW
$90
8/19Tue
1 stopDelta
6h 22mBOI-ORD
$90
10/11Sat
nonstopUnited Airlines
3h 39mBOI-ORD
$94
8/30Sat
2 stopsDelta
10h 37mBOI-MDW
$95
8/5Tue
nonstopAlaska Airlines
4h 04mPDX-ORD
$116
1/9Fri
1 stopAlaska Airlines
7h 00mBOI-ORD
$117

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Last minute flights from Oregon to Illinois

Last minute flight, train and bus deals

7/18Fri
multi-stopSpirit Airlines
12h 53mPDX-ORD
7/19Sat
multi-stopSpirit Airlines
15h 29mORD-PDX
$222
7/16Wed
multi-stopFrontier
9h 45mPDX-ORD
7/31Thu
multi-stopFrontier
6h 31mORD-PDX
$231
7/17Thu
multi-stopAmerican Airlines
7h 11mBOI-ORD
7/19Sat
multi-stopAmerican Airlines
6h 54mORD-BOI
$365
7/17Thu
multi-stopAmerican Airlines
7h 11mBOI-ORD
7/19Sat
nonstopAmerican Airlines
3h 51mORD-BOI
$373
7/18Fri
nonstopSouthwest
3h 20mBOI-MDW
7/21Mon
multi-stopSouthwest
8h 30mMDW-BOI
$398
7/18Fri
nonstopSouthwest
3h 20mBOI-MDW
7/21Mon
multi-stopSouthwest
11h 35mMDW-BOI
$403
7/15Tue
multi-stopUnited Airlines
9h 24mBOI-ORD
7/22Tue
nonstopUnited Airlines
4h 07mORD-BOI
$430
7/19Sat
nonstopUnited Airlines
3h 26mBOI-ORD
7/23Wed
multi-stopUnited Airlines
9h 47mORD-BOI
$434
7/16Wed
multi-stopAlaska Airlines
8h 21mRDM-ORD
7/19Sat
multi-stopAlaska Airlines
9h 21mORD-RDM
$676
7/16Wed
multi-stopAlaska Airlines
12h 06mMFR-ORD
7/20Sun
multi-stopAlaska Airlines
6h 47mORD-MFR
$720

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Everything you need to know for your flight to Illinois

Cabin class types available on flights to Oregon

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