$60 Find Cheap Flights from Illinois to Oregon

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Low seasonJanuary
Cheapest flight$60
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from St. Louis to Portland

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?

    Air Canada connects Illinois to Oregon with 19 flights per week. United Airlines also offers 19 flights per week, while Southwest follows with 13 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 $281.

  • What is the cheapest day to fly to Oregon?

    Based on KAYAK data, the cheapest day to fly to Oregon is Wednesday where round-trip tickets can be as cheap as $332. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $401 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 $317 on average. Morning departures are around 15% 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 $474.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Illinois found in the last 72 hours was to Portland, at $198 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 72 hours was $198.

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

    The cheapest month for flights from Illinois to Oregon is October, when tickets cost $342 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $698 and $558 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 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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 118 direct flights each week.

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

    There are around 17 direct flights from within Illinois to Oregon every day. Most flights (68%) depart in the afternoon.

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

    Each week there are around 118 direct flights from within Illinois to Oregon. The most common day for departures is Friday, with 20% of flights taking off on this day.

  • How long is the flight to Oregon?

    An average nonstop flight from Illinois to Oregon takes 8h 57m, covering a distance of 1670 miles. The shortest route is Chicago Midway Airport (MDW) to Boise (BOI) with an average flight time of 3h 35m.

  • 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 118 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 (65% of total searches to Oregon). The next most popular destinations are Boise (19%) and Eugene (6%). Searches for flights to Redmond (5%), to Medford (3%) and to North Bend (1%) 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 4257 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

3 hour delay. Had to change plans and was still delayed.

2.0 MediocreAnonymous, Jan 2026
SFO - SAN
Read more Southwest reviews

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

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.

You need categories to note when food and entertainment are not available. Alaska's system would not update flight info on the board for this flight, so there was some confusion after deplaning from the previous flight as to which gate and depart time were accurate for this flight.

You need categories to denote when food and entertainment are not available.

Alaska is generally the airline I fly nearly all the time. I nearly always have wonderful experiences on Alaska and never a complaint. However, this entire flight felt like we were in the cheap seats the entire time and I had even upgraded to a cushier seat. For an over six hour flight (that became 7 hours) there was no online entertainment. I couldn’t connect to Wi-Fi and we were offered one snack and one drink. We were instructed to go to a particular baggage claim and 30 minutes later our bag still hadn’t come out and it turned out it was the wrong carousel announced. So overall, this flight was a series of mishaps really less than mediocre service even though flight attendants were wonderful.

Alaska is a great airline. Unfortunately, our flight was canceled in a really late hour and it caused a lot of hardship in my travel process.

More comfortable than the flight to Los Angeles. But food was mediocre again. Attendants kind and courteous.

The flight attendants were nice, but the cabin and seats were uncomfortable.

Alaska Airlines has the best service of airlines I have flown the last couple years. I always choose them first.

The snack pretzels have garlic. just use normal pretzels. Tomatoijuice instead of only bloody mary mix

I haven’t flown in over 20 years and had my grandkids, so I had lots of questions. They were very polite and helpful . Thank you.

I know there were a lot of delayed flights, mine from Portland to Eugene was delayed by 3 hours, but not from one employee was there a" we are so sorry about the delay or is there anything we could get you, I thought it was very un-professional and rude.

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

Alaska was fine as usual. My frustration came with accessing boarding passes. On the first trip, I could only get one to print ans took a picture of the second one. On our return trip, the system was down? Friends who booked directly with Alaska had theirs process. I even tried the 800 number and had others try it too. It said something in Spanish and hung up. The agent at the airport succeeded.

Delayed and cancelled flights were hard and very stressful, both ways!

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

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.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

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.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

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

Everything you need to know for your flight to Oregon

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.