$85 Find Cheap Flights from Portland to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Illinois departing on 7/1. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Illinois.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Illinois.
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Best Illinois Flight Deals from Portland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$171
Moline
Moline1 stop$251
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$419
Champaign
Champaign1 stop$506
St. Louis
St. Louis1 stop$244
Marion
Marion2 stops$537
Chicago
Chicago1 stop$171
Moline
Moline1 stop$251
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$419
Champaign
Champaign1 stop$506
St. Louis
St. Louis1 stop$244
Marion
Marion2 stops$537

Cheap Flights from Portland to Illinois

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Illinois

Thu, Aug 21 - Sat, Aug 30
 Logo
2:35 pm - 11:43 pmPDX-ORD
7h 08m1 stop
 Logo
7:00 am - 10:39 pmORD-PDX
17h 39m1 stop
Wed, Jul 9 - Mon, Jul 14
Spirit Airlines Logo
3:10 pm - 6:03 amPDX-ORD
12h 53m1 stop
Spirit Airlines Logo
7:08 am - 2:15 pmORD-PDX
9h 07m1 stop
$174Spirit Airlines
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Sat, Sep 6 - Wed, Sep 10
Alaska Airlines Logo
5:50 pm - 11:59 pmPDX-ORD
4h 09mnonstop
Alaska Airlines Logo
2:07 pm - 4:36 pmORD-PDX
4h 29mnonstop
$181Alaska Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
1:30 pm - 7:30 pmPDX-MDW
4h 00mnonstop
Southwest Logo
3:50 pm - 6:05 pmMDW-PDX
4h 15mnonstop
$181Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Alaska Airlines Logo
5:50 pm - 11:59 pmPDX-ORD
4h 09mnonstop
Alaska Airlines Logo
8:00 am - 12:24 pmORD-PDX
6h 24m1 stop
$191Alaska Airlines
Find Deal
Wed, Aug 20 - Tue, Aug 26
Southwest Logo
9:05 pm - 7:10 amPDX-MDW
8h 05m1 stop
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
$191Southwest
Find Deal
Tue, Jul 1 - Thu, Jul 3
United Airlines Logo
11:59 pm - 6:00 amPDX-ORD
4h 01mnonstop
United Airlines Logo
9:10 am - 11:43 amORD-PDX
4h 33mnonstop
$234United Airlines
Find Deal
Sat, Aug 30 - Tue, Sep 2
American Airlines Logo
5:34 am - 4:58 pmPDX-MLI
9h 24m1 stop
American Airlines Logo
5:50 pm - 10:59 pmMLI-PDX
7h 09m1 stop
$251American Airlines
Find Deal
Fri, Jul 4 - Fri, Jul 11
United Airlines Logo
7:00 am - 3:07 pmPDX-MLI
6h 07m1 stop
United Airlines Logo
3:45 pm - 10:29 pmMLI-PDX
8h 44m1 stop
$259United Airlines
Find Deal
Fri, Aug 29 - Tue, Sep 2
American Airlines Logo
11:59 pm - 10:12 amPDX-MLI
8h 13m1 stop
American Airlines Logo
6:18 pm - 11:20 pmMLI-PDX
7h 02m1 stop
$270American Airlines
Find Deal
Useful Info

KAYAK's insights & trends for Portland to Illinois flights

Get data-powered insights and trends into flights from Portland to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Portland to Illinois flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Portland to Illinois.

The cheapest ticket to Illinois from Portland found in the last 72 hours was to Chicago, at $236 round-trip. The most popular route is from Portland (PDX) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $236.

Can I save money by flying with a layover from Portland to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $396 on average.

What is the cheapest month to fly from Portland to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Illinois is January, when tickets cost $263 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $445 and $420 respectively.

What’s the cheapest day of the week to fly from Portland to Illinois?

The average price of all round-trip flights from Portland to Illinois clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Illinois on a Friday and more expensive on a Sunday. On your return trip to Portland, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

How far in advance should I book a flight from Portland to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Illinois, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Illinois, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$85
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Portland to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Portland to Illinois?

    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 Portland to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Illinois 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 Portland to Illinois?

    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 Portland to Illinois 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 Portland to Illinois?

    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 Portland to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $311 on average. Morning departures are around 70% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $529.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Portland to the following destinations at these prices or less: Chicago $171 one-way - $342 round-trip

Top 5 airlines serving from Portland to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Portland to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Illinois? 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 10000 reviews
8.1Boarding
7.8Comfort
7.1Food
7.1Entertainment
8.5Crew
Airline reviews

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

10.0 Excellentmarlene, Jun 2025PDX - SMF
Read more Alaska Airlines reviews

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

No WiFi available. It was too late to order food also. Guy next to me was huge (not fat) so had his shoulder & thigh next to me the whole way. Plane was delayed leaving PDX due to 8 other planes waiting. Not my best Alaska airlines flight.

Check in, they should have told me that upon arrival i needed to exit the secure area and re-check in with Eva Air. I wasn't sure what to do upon arrival at S.F.

The direct service from Logan to PDX made travel so easy, I really appreciate this route. Pilots were very communicative with passengers about conditions and expectations. Everyone on staff was pleasant and helpful. Boarding was easy and efficient.

Flight last minute delayed 2 hours for crew calling out sick

Husband was new to the wheelchair accommodations this trip. What a blessing that was. All employees were helpful and customer service was excellent

Seats are still too crowded and uncomfortable on long flights like this cross country one.

Laney was very helpful. I am computer illiterate. She helped me obtain a boarding pass and preferred seat. She was warm, friendly, helpful, and smiled. I was impressed.

The actual flight I was rescheduled onto was from Seattle to Bozeman. The flight itself was fine, but due to delays/air traffic issues i spent the day hanging out at the Seattle airport and had to miss a day of work.

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

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.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

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