$122 Find Cheap Flights from Illinois to Oregon - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Useful Info

Good to know

Low season

January

Cheapest flight

$122
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago O'Hare Airport to Boise

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 (45 flights per week), American Airlines (21 flights per week), and Air Canada (21 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 $240.

  • 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 $350. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $435 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 $338 on average. Morning departures are around 13% 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 $457.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Illinois found in the last 5 days was to Portland, at $246 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 $246.

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

    The cheapest month for flights from Illinois to Oregon is May, when tickets cost $215 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $281 and $271 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 48% 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 203 direct flights each week.

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

    There are around 29 direct flights from within Illinois to Oregon every day. Most flights (41%) depart in the afternoon.

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

    Each week there are around 203 direct flights from within Illinois to Oregon. The most common day for departures is Sunday, with 16% of flights taking off on this day.

  • How long is the flight to Oregon?

    An average nonstop flight from Illinois to Oregon takes 8h 36m, covering a distance of 1670 miles. The shortest route is Chicago Midway Airport (MDW) to Boise (BOI) with an average flight time of 3h 30m.

  • 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 203 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 (68% of total searches to Oregon). The next most popular destinations are Boise (24%) and Medford (4%). Searches for flights to Redmond (4%) 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.
8.0
SouthwestOverall score based on 4204 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

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.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

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.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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.

The flight left almost an hour and a half late because Alaska Airlines didn’t have anyone there who was qualified to drive or tow the airplane from its overnight parking spot to our gate. Because of that debacle, MANY passengers, including me, missed our connecting flights.

I have a good impression with the staff's friendliness and helpfulness and with the confort.

Several gate changes and then the plane kept getting delayed. The delay is understandable but this constant gate change I think twice or three times is just ridiculous.

Gated at different concourse than was supposed to be, with tight connexion

Flight was delayed over an hour. Flight attendant couldn’t get cc machine to work, so on board food was unavailable. Not Alaska’s finest day…

Alaska Airlines is a great airline. I had no idea. Lots of legroom.

I always fly Alaska. Unless they don’t go where I need to go. They are the best

On time departure & early arrival made the long day much better

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.

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.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

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.

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.

Pretty turbulent, but not anyone’s fault. They got us there. Impressed that they carried on with a drink service.

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

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

We were re routed due to a flight cancellation. We did not fly out of Miami. We originally booked first class and were moved to coach without being compensated.

Everything you need to know for your flight to Oregon

Cabin class types available on flights to Illinois