$70 Find Cheap Flights from Illinois to Oregon

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Low seasonJanuary
High seasonJuly
Cheapest flight$70
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport 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 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 $202.

  • 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 $304. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $383 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 $212 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 evening, which is peak travel time and where the average cost of a ticket is $385.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Illinois found in the last 72 hours was to Portland, at $223 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 $223.

  • 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 $288 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $705 and $623 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. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

  • How long is the flight to Oregon?

    An average nonstop flight from Illinois to Oregon takes 8h 32m, 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.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Portland (73% of total searches to Oregon). The next most popular destinations are Boise (12%) and Medford (6%). Searches for flights to Eugene (5%), to Redmond (3%) and to North Bend (1%) are also popular.

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
Alaska AirlinesOverall score based on 9968 reviews
7.9Comfort
8.2Boarding
7.1Food
8.5Crew
7.1Entertainment
Airline reviews

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

2.0 MediocreAnonymous, Apr 2025SNA - PDX
Read more Alaska Airlines reviews

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Everything was good. However, the selections of movies and TV shows were boring and unexciting. It was disappointing.

Personal demeanor not good on flight returning to LAX..Great and superb on the way to Portland

Very helpful with my mother who needed a wheelchair at both ends and everything went as expected

The flight was great, the crew was great. Our complaint was that there are no TV screens built into the seats. We used our tablets but drained my battery just watching a movie. The movie and TV selection were okay but not great.

Plane was delayed and got me in past bedtime. But more importantly, my tsa precheck number wasn’t on my ticket so had to deal with the general line. Oh well, guess the delay helped that situation.

The Crew was super nice but the plane was subpar at best. Filthy in some aspects. Internet only worked half the time and not with everything.

They were all very kind, but misinformed. We came from Idaho to Spokane, Washington and were told that my husband and I could get passes to sit with William until his flight took off. (William has special needs.) When we got to the airport we were told only one of us could sit with William, so my husband and I were separated for 2 hours as I sat with William. What is WORSE . . . is I asked for a meet and assist in Portland and they NEVER showed up. NOR did they call me to tell me they hadn't met him. William's grandmother in Portland is disabled and can't walk into find him. Fortunately, some kind citizens helped him to find the meeting point with me on the phone in terror. I have a heart condition, complete with prior heart attack, this type of customer service is UNACCEPTABLE.

Could have had more of a beverage selection than water and apple juice.

Crew was overly aggressive with rules enforcement and not friendly in general.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

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.

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Packed commercial flight was as comfortable as can be expected

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Book cheap flights from Illinois to Oregon

Recent round-trip flight deals

6/3Tue
1 stopSpirit Airlines
6h 55mORD-PDX
6/10Tue
1 stopSpirit Airlines
15h 15mPDX-ORD
$154
9/12Fri
nonstopUnited Airlines
3h 46mORD-BOI
9/19Fri
nonstopUnited Airlines
3h 33mBOI-ORD
$155
7/16Wed
1 stopDelta
5h 53mMDW-BOI
7/26Sat
1 stopDelta
6h 49mBOI-MDW
$175
6/13Fri
1 stopDelta
5h 54mORD-BOI
6/15Sun
1 stopDelta
5h 12mBOI-ORD
$175
5/24Sat
nonstopSouthwest
4h 20mMDW-PDX
5/31Sat
nonstopSouthwest
4h 00mPDX-MDW
$179
9/17Wed
1 stopAlaska Airlines
9h 40mORD-BOI
9/21Sun
1 stopAlaska Airlines
12h 18mBOI-ORD
$210
5/30Fri
1 stopSouthwest
8h 25mMDW-PDX
6/7Sat
nonstopSouthwest
3h 55mPDX-MDW
$213
6/3Tue
nonstopAlaska Airlines
4h 23mORD-PDX
6/11Wed
nonstopAlaska Airlines
4h 05mPDX-ORD
$227
5/28Wed
nonstopAmerican Airlines
4h 24mORD-PDX
6/17Tue
nonstopAmerican Airlines
3h 56mPDX-ORD
$274
6/3Tue
1 stopAmerican Airlines
8h 37mSTL-PDX
6/6Fri
1 stopAmerican Airlines
5h 59mPDX-STL
$277

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Recent one-way flight deals

6/3Tue
1 stopSpirit Airlines
6h 55mORD-PDX
$70
6/7Sat
nonstopUnited Airlines
3h 58mORD-BOI
$78
5/28Wed
1 stopAlaska Airlines
9h 05mORD-BOI
$87
5/30Fri
1 stopDelta
5h 57mMDW-BOI
$88
5/30Fri
1 stopDelta
9h 04mORD-BOI
$88
5/28Wed
nonstopAlaska Airlines
4h 23mORD-PDX
$90
5/30Fri
1 stopSouthwest
8h 25mMDW-PDX
$99
7/4Fri
1 stopSouthwest
10h 35mMDW-PDX
$105
7/4Fri
1 stopAmerican Airlines
8h 54mSTL-PDX
$114
5/31Sat
1 stopAmerican Airlines
6h 19mMLI-PDX
$115

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Last minute flights from Illinois to Oregon

Last minute flight, train and bus deals

5/1Thu
multi-stopFrontier
19h 47mSTL-PDX
5/4Sun
multi-stopFrontier
24h 49mPDX-STL
$188
5/5Mon
multi-stopSpirit Airlines
7h 56mORD-PDX
5/7Wed
multi-stopSpirit Airlines
9h 45mPDX-ORD
$208
5/5Mon
nonstopAlaska Airlines
4h 33mORD-PDX
5/6Tue
multi-stopAlaska Airlines
6h 26mPDX-ORD
$254
5/3Sat
multi-stopDelta
5h 15mORD-BOI
5/6Tue
multi-stopDelta
6h 29mBOI-ORD
$332
5/3Sat
multi-stopAmerican Airlines
7h 33mORD-BOI
5/5Mon
multi-stopAmerican Airlines
6h 34mBOI-ORD
$360
5/1Thu
multi-stopDelta
8h 16mMDW-BOI
5/4Sun
multi-stopDelta
7h 52mBOI-MDW
$387
5/3Sat
nonstopUnited Airlines
4h 10mORD-BOI
5/6Tue
multi-stopUnited Airlines
7h 37mBOI-ORD
$402
5/2Fri
multi-stopAlaska Airlines
6h 22mSTL-PDX
5/5Mon
multi-stopAlaska Airlines
5h 59mPDX-STL
$427
5/3Sat
nonstopUnited Airlines
4h 10mORD-BOI
5/5Mon
multi-stopUnited Airlines
9h 22mBOI-ORD
$430
5/2Fri
multi-stopAmerican Airlines
9h 09mMLI-PDX
5/4Sun
multi-stopAmerican Airlines
7h 26mPDX-MLI
$489

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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.

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