$90 Find Cheap Flights from Oregon to Illinois

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Good to know

Low seasonJanuary
Cheapest flight$85
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Portland to St. Louis

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 airlines fly most frequently to Illinois?

    Oregon and Illinois are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (23 flights per week), Air Canada (21 flights per week), and Alaska Airlines (19 flights per week).

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 91% of all flights arriving there.

  • 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 $219.

  • 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 $430. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $533 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 $320 on average. Morning departures are around 51% 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 $483.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Oregon found in the last 72 hours was to Chicago O'Hare Intl Airport, at $198 round-trip. The most popular route is Eugene (EUG) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $198.

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

    The cheapest month for flights from Oregon to Illinois is May, when tickets cost $371 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $858 and $584 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, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Oregon, there are direct flights to Illinois from 1 city. This city is Portland and there are 148 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 26 direct flights from within Oregon to Illinois every day. Most flights (79%) depart in the morning.

  • How many direct flights to Illinois are there each week?

    Each week there are around 180 direct flights from within Oregon to Illinois. The most common day for departures is Friday, with 19% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Oregon to Illinois takes 9h 41m, covering a distance of 1649 miles. The shortest route is Boise (BOI) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 24m.

  • How many long-haul flights are there to Illinois each week?

    Each week, there are 141 medium-haul flights (3-6 hour flight duration) and 7 short-haul flights (up to 3 hour flight duration) to Illinois. There aren't any long-haul flights (6-12 hour flight duration).

  • 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 (11%) and Peoria (1%). Searches for flights to Springfield (1%), to Moline (1%) and to Bloomington (1%) 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 11648 reviews
7.8Comfort
7.0Entertainment
8.1Boarding
7.1Food
8.5Crew
Airline reviews

Before I even boarded this old white man , a fat Samoan lady, and a short brown guy were at the desk. They asked if we could have 15 volunteers to get free checked bags cause it was a full flight. I waited in line, I got up to the short brown guy and he asked for my boarding pass and I showed him, he said that he can’t check my bag because I wasn’t given a seat yet. So he had me go to the next line with the old white guy, but before I switched lines I asked him, well if I go to that line, will I be able to check my bag so I waited in line and he said yeah, it doesn’t matter , I’m good. So I switch lines and wait in the line of the old white man, with every guest before me he was very sweet , making small talk, smiling and had great eye contact( all of the people he was talking to was white) I come up and he doesn’t look at me , then says I’ll be right with you, I wait for him to initiate and when he does he’s like what’s up? I was like the man next to you told me I needed to get checked in before I can check my bag. He’s like what’s your last name and I say Valenzuela , and he said we’re not there yet, all while not smiling, no eye contact like he was with the other guests. He said we’re will call you when I get to you. So I go sit down and I’m sitting down for less than a minute and he calls me and someone else. I go up and say Valenzuela and he’s like who are you and I’m like Valenzuela , he’s like hmm and says don’t go anywhere and calls someone else. I finally get my seat and I go back to the short brown man and ask if I can check my bag and he said there isn’t any room available and I was like? Wait you told me and then the fat Samoan lady said yeah we don’t need anymore bags thank you. I was dumbfounded and just walked away. So rude. Terrible experience and terrible communication on their end.

2.0 MediocreAnonymous, Jan 2026
PDX - BUR
Read more Alaska Airlines reviews

Before I even boarded this old white man , a fat Samoan lady, and a short brown guy were at the desk. They asked if we could have 15 volunteers to get free checked bags cause it was a full flight. I waited in line, I got up to the short brown guy and he asked for my boarding pass and I showed him, he said that he can’t check my bag because I wasn’t given a seat yet. So he had me go to the next line with the old white guy, but before I switched lines I asked him, well if I go to that line, will I be able to check my bag so I waited in line and he said yeah, it doesn’t matter , I’m good. So I switch lines and wait in the line of the old white man, with every guest before me he was very sweet , making small talk, smiling and had great eye contact( all of the people he was talking to was white) I come up and he doesn’t look at me , then says I’ll be right with you, I wait for him to initiate and when he does he’s like what’s up? I was like the man next to you told me I needed to get checked in before I can check my bag. He’s like what’s your last name and I say Valenzuela , and he said we’re not there yet, all while not smiling, no eye contact like he was with the other guests. He said we’re will call you when I get to you. So I go sit down and I’m sitting down for less than a minute and he calls me and someone else. I go up and say Valenzuela and he’s like who are you and I’m like Valenzuela , he’s like hmm and says don’t go anywhere and calls someone else. I finally get my seat and I go back to the short brown man and ask if I can check my bag and he said there isn’t any room available and I was like? Wait you told me and then the fat Samoan lady said yeah we don’t need anymore bags thank you. I was dumbfounded and just walked away. So rude. Terrible experience and terrible communication on their end.

The flight was delayed, but once it arrived everything moved right along.

Coke zero offered...good. The proptness of flight was late. This has been a everytime thing for my last 9 flights. And is putting alot of pressure on my connecting flights. Not a bit punctual. I am always early, but Ak. Airlines is not. And people i happen fly beside, parrot the same thing. The baggage delivery to baggage claim, is not prompt. Its slowwwww. The seats are poorly padded, very crowd. We need more room, not padding the airlines bottom line. Its like a cattle car. More leg room, more side to side room. And attendants need upgrade of verbal skills. I have been faithful to Ak. A., but it will change if changes are not made. Not the only planes in the sky.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Everything was great except for one piece of our luggage was severely damaged and crushed. There were no agents available at baggage claim and the hold time on the phone was over 3 hours. So therefore we were unable to file a complaint. We will be speaking to Alaska Airlines about replacing our luggage when we check in for our return flight.

Great airline. Sat next to a really big person tho

I always choose Alaska when I can. Every thing seems to run more efficiently with them.

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.