$136 Find Cheap Flights from Illinois to Oregon - Compare and Save

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Low season

January

Cheapest flight

$136
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to Eugene

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 airlines fly most frequently to Oregon?

    Illinois and Oregon are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (49 flights per week), Air Canada (37 flights per week), and American Airlines (24 flights per week).

  • How many airports are there in Oregon?

    There are 6 airports in Oregon. The busiest airport is Portland Airport (PDX), with 74% of all flights arriving there.

  • 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 $261.

  • What is the cheapest day to fly to Oregon?

    Based on KAYAK data, the cheapest day to fly to Oregon is Tuesday where round-trip tickets can be as cheap as $358. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $450 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 $348 on average. Morning departures are around 9% 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 $461.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Illinois found in the last 5 days was to Portland, at $317 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 5 days was $317.

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

    The cheapest month for flights from Illinois to Oregon is February, when tickets cost $203 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $294 and $282 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 4 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

  • How many cities have direct flights to Oregon?

    From Illinois, there are direct flights to Oregon from 1 city. This city is Chicago and there are 223 direct flights each week.

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

    There are around 32 direct flights from within Illinois to Oregon every day. Most flights (49%) depart in the afternoon.

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

    Each week there are around 223 direct flights from within Illinois to Oregon. The most common day for departures is Sunday, with 17% of flights taking off on this day.

  • How long is the flight to Oregon?

    An average nonstop flight from Illinois to Oregon takes 8h 52m, covering a distance of 1670 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Boise (BOI) with an average flight time of 3h 51m.

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

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Oregon. Instead, there are 223 medium-haul flights (3-6 hour flight duration), with the most arriving from Chicago.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Portland (71% of total searches to Oregon). The next most popular destinations are Boise (22%) and Medford (4%). Searches for flights to Redmond (3%) and to Yakima (0%) 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.
7.9
Alaska AirlinesOverall score based on 13125 reviews
7.0Food
7.8Comfort
8.5Crew
7.0Entertainment
8.1Boarding
Airline reviews

I bought this flight for my mom to come to Houston to see her grandkids and on the way here, their flight was delayed over and over and she didn't get until midnight and she was supposed to be in at 5: 30pm. My mom is almost 70 with a bad knee so that's a long time to be stuck in an airport because her first flight was delayed and she missed her second flight and had to wait for the last fight of the day just to make it. Not only that, which is ridiculous because if a flight is delayed the next fight should have waited for them, on the way home, once again her flight was delayed and by the time she would have gotten to Portland she would have missed her flight to Redmond. So we called and had to get her flight changed because of that. Thankfully she was flexible and flew out the next day, but the Portland trip didn't happen. I am happy that Alaska did make it right by getting her a new flight and upgrading her seats but there should be holding the next flights if the flight is getting there within a few minutes of them boarding. If one flight is delayed, the next flight should be delayed just to accommodate people. Older people having to wait in the airport in uncomfortable chairs for hours on end is not the best for my almost 70-year-old mom.

6.0 GoodHannah, Oct 2026
Read more Alaska Airlines reviews

I bought this flight for my mom to come to Houston to see her grandkids and on the way here, their flight was delayed over and over and she didn't get until midnight and she was supposed to be in at 5: 30pm. My mom is almost 70 with a bad knee so that's a long time to be stuck in an airport because her first flight was delayed and she missed her second flight and had to wait for the last fight of the day just to make it. Not only that, which is ridiculous because if a flight is delayed the next fight should have waited for them, on the way home, once again her flight was delayed and by the time she would have gotten to Portland she would have missed her flight to Redmond. So we called and had to get her flight changed because of that. Thankfully she was flexible and flew out the next day, but the Portland trip didn't happen. I am happy that Alaska did make it right by getting her a new flight and upgrading her seats but there should be holding the next flights if the flight is getting there within a few minutes of them boarding. If one flight is delayed, the next flight should be delayed just to accommodate people. Older people having to wait in the airport in uncomfortable chairs for hours on end is not the best for my almost 70-year-old mom.

If you had direct flights to Denver from Santa Rosa, I would be a frequent flyer. Nice experience.

There is not enough space in the cabin for bags and so I had to have my check to the last second.

My experience was great with Alaska Airlines. Fantastic customer care

Overall, excellent, including the warmth, friendliness and equanimity of all the employees,

People were friendly and helpful, and even under stress of a short time between connecting flights, kept their equanimity.

Significant unexplained delay in boarding caused me to nearly miss connecting flight. Cabin crew was helpful in expediting deplaning and gate notification .

Super narrow seats, no in flight entertainment for long direct flight and limited snacks of 1 packet of cookies. Nice crew and patient staff.

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

It was as expected and I was grateful for the wheel chair help and ease of use.

Tight seats. Be prepared to sit in the middle if you are in boarding group C.

This was a connecting flight for me and I had already traveled for 7 hours. First, the Pilot didn’t show up and then the gate changed twice, after which the flight was rescheduled for 2 hours later. This made me late and I had to make other transportation arrangements to get home to Astoria another 1 hour & 45 minutes away. This cost me $250 more than it should have. Will not fly southwest again.

Long layover in Chicago. Wish that could have been lessened.

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

The Pilot was one of the best I've had, very informative about turbulence and got us to our destination early

Friendly boarding crew. Better could have been a bit more substantial food for this 3 plus hour flight.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Pilot Erika DeLong made us feel safe and at ease in a frankly scary time to be flying. Her warm smile and greeting and excellent command of the aircraft in foggy bumpy weather helped us all to calm our nerves and get us home safely.

Not enough room between rows and food was gross. $160 baggage charge?! Never again.

East Lounge in Denver was terrible. Turning away active military on orders? Really? Sad.

Clean and plenty of room for handbaggage. Leg room was cramped compared with the 777 from Frankfurt.

they made me check my carryon. There was space in the overhead bins.

Cramped and uncomfortable seats. Not enough room for 6’2” person such as myself.

We were delayed a long time. We waited for “catering”. We didn’t get any food or accommodation for our wait. It made us land well after dinner time at our destination.

It was my first time flying with Alaska Airlines and it was a pleasure!

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

Packed commercial flight was as comfortable as can be expected

My seat was very worn. Otherwise I had an excellent flight

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