$106 Find Cheap Flights from Illinois to Oregon

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Illinois to Oregon departing on 8/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 13% 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?

    Illinois and Oregon are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (46 flights per week), American Airlines (29 flights per week), and Air Canada (29 flights per week).

  • How many airports are there in Oregon?

    There are 6 airports in Oregon. The busiest airport is Portland Airport (PDX), with 73% 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 Eugene Airport (EUG), with an average flight price of $228.

  • 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 $331. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $407 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 $329 on average. Morning departures are around 7% 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 $466.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Illinois found in the last 3 days was to Portland, at $244 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 3 days was $244.

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

    The cheapest month for flights from Illinois to Oregon is April, when tickets cost $327 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $644 and $493 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 56% 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 217 direct flights each week.

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

    There are around 31 direct flights from within Illinois to Oregon every day. Most flights (44%) depart in the evening.

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

    Each week there are around 217 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 05m, 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 217 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 (72% of total searches to Oregon). The next most popular destinations are Boise (12%) and Eugene (7%). Searches for flights to Medford (5%), to Redmond (4%) and to North Bend (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 4262 reviews
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

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.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Couldn’t order food for the family because all the good food was unavailable. We opted for bringing something on with us. I also didn’t like that I had to have T-mobile for online movies. Stupid.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

The flight crew home was so, so friendly and HILARIOUS. I’ll keep flying Alaska like I have for the last 30+ years!

Deboarding the plane was chaos. The passengers in the back of the plane started deplaning before the passengers in the middle of the plane could even retrieve their overhead bags. The staff of the plane did nothing to help.

Enforce the one bag rule for carry ons. Don't allow people to have 2 and 3 carry ons. Make baggage gets loaded onto the correct plane. My bag didn't get put onto my last flight so I didn't get it until the next day.

onboard snack was pretzels, but the FA was super nice when my neighbor asked for cookies instead and also brought some for me. :)

On time. .breakfast was especially good. First class service was special

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

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.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

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.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

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.