$69 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 5/17. 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.
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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$139
Moline
Moline2 stops$335
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$379
Champaign
Champaign1 stop$506
Springfield
Springfield1 stop$423
St. Louis
St. Louis1 stop$227
Chicago
Chicago1 stop$139
Moline
Moline2 stops$335
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$379
Champaign
Champaign1 stop$506
Springfield
Springfield1 stop$423
St. Louis
St. Louis1 stop$227

Cheap Flight Deals from Portland to Illinois (PDX-USIL)

 
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.

Recent round-trip flight deals from Portland to Illinois

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Portland to Illinois.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
1:37 pm - 5:25 amPDX-ORD
13h 48m1 stop
Spirit Airlines Logo
11:50 am - 4:45 pmORD-PDX
6h 55m1 stop
$139Spirit Airlines
Find Deal
Thu, May 29 - Tue, Jun 3
Spirit Airlines Logo
5:40 pm - 5:25 amPDX-ORD
9h 45m1 stop
Spirit Airlines Logo
11:50 am - 4:45 pmORD-PDX
6h 55m1 stop
$150Spirit Airlines
Find Deal
Thu, May 29 - Tue, Jun 3
Alaska Airlines Logo
7:00 am - 1:07 pmPDX-ORD
4h 07mnonstop
Alaska Airlines Logo
7:00 am - 9:23 amORD-PDX
4h 23mnonstop
$218Alaska Airlines
Find Deal
Sat, May 10 - Wed, May 21
Alaska Airlines Logo
5:51 pm - 11:56 pmPDX-ORD
4h 05mnonstop
Alaska Airlines Logo
7:00 am - 9:23 amORD-PDX
4h 23mnonstop
$219Alaska Airlines
Find Deal
Mon, May 19 - Sat, May 24
American Airlines Logo
3:14 pm - 12:32 amPDX-ORD
7h 18m1 stop
American Airlines Logo
8:22 pm - 11:04 pmORD-PDX
4h 42mnonstop
$252American Airlines
Find Deal
Thu, Jun 5 - Sat, Jun 14
Southwest Logo
2:30 pm - 8:25 pmPDX-MDW
3h 55mnonstop
Southwest Logo
10:05 pm - 12:25 amMDW-PDX
4h 20mnonstop
$253Southwest
Find Deal
Thu, Jun 5 - Mon, Jun 9
Southwest Logo
2:30 pm - 8:25 pmPDX-MDW
3h 55mnonstop
Southwest Logo
8:00 pm - 1:05 amMDW-PDX
7h 05m1 stop
$259Southwest
Find Deal
Thu, Jun 5 - Mon, Jun 9
United Airlines Logo
11:59 pm - 9:31 amPDX-STL
7h 32m1 stop
United Airlines Logo
5:00 am - 9:42 amSTL-PDX
6h 42m1 stop
$264United Airlines
Find Deal
Tue, Jul 29 - Sun, Aug 3
American Airlines Logo
12:09 am - 6:05 amPDX-ORD
3h 56mnonstop
American Airlines Logo
7:17 am - 9:39 amORD-PDX
4h 22mnonstop
$272American Airlines
Find Deal
Fri, Jun 20 - Wed, Jun 25
United Airlines Logo
5:00 am - 1:15 pmPDX-ORD
6h 15m1 stop
United Airlines Logo
4:02 pm - 6:34 pmORD-PDX
4h 32mnonstop
$274United Airlines
Find Deal
Tue, May 20 - Fri, May 23
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 $238 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 $238.

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.

No, with an average price for the route of $658, prices are generally cheapest when you fly direct.

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 $417 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 Wednesday and more expensive on a Sunday. On your return trip to Portland, you should consider flying back on a Wednesday, and avoid Mondays 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 seasonMay
Cheapest flight$69
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 3% 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 $356 on average. Morning departures are around 57% 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 $560.

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 $170 one-way - $358 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 9968 reviews
7.9Comfort
8.2Boarding
7.1Entertainment
7.1Food
8.5Crew
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025PDX - PHX
Read more Alaska Airlines reviews

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

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

It was a short flight so no refreshments or entertainment which was fine.

Flying in both directions across country the gate designated on my boarding pass was wrong. From w to e across the country the passenger next to me coughed the entire way.

Although both planes (flights) had mechanical issue delaying both of my flights, the crew members handled everything with ease. Both flights had the smoothest take off and landing. I opted to upgrade my seat to first class and really lucked out getting the seat at the very front of the plane. Awesome treat to myself. I really enjoyed my flight.

The staff from check-in counter to the flight crew were great. Flight was right on schedule. 10/10

Changed flight from San Fran to Seattle Then with a Delayed takeoff barely made my connection Waited over an hour for luggage 😜

It was good. There was a mistake made in Seattle. Somehow we were bumped out of our seats as if we weren't on the flight anymore. The woman at the gate caught it and announced our name to come up and she fixed it.

I wouldn’t fly with Alaska again if you paid me.

I appreciated Alaska Airlines very much, they are expanding traveling locations globally as they partnered with another company and am excited and looking forward to our next traveling adventure with this great Airline. Thank you kindly

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

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.

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.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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.

Paid extra for a “comfy seat” which was anything but!

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

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