$68 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 1/16. 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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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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Cheap Flights from Portland to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$227
Moline
Moline1 stop$310
Peoria
Peoria1 stop$309
Bloomington
Bloomington1 stop$564
Springfield
Springfield2 stops$801
St. Louis
St. Louis1 stop$193
Paducah
Paducah1 stop$298
Chicago
Chicagononstop$227
Moline
Moline1 stop$310
Peoria
Peoria1 stop$309
Bloomington
Bloomington1 stop$564
Springfield
Springfield2 stops$801
St. Louis
St. Louis1 stop$193
Paducah
Paducah1 stop$298

Book Cheap Portland to Illinois Plane Tickets

 
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, Jan 29 - Sun, Feb 1
Frontier Logo
11:28 am - 9:06 pm
PDX
-
STL
7h 38m1 stop
Frontier Logo
9:32 pm - 11:18 am
STL
-
PDX
15h 46m1 stop
$193Frontier
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
11:28 am - 9:06 pm
PDX
-
STL
7h 38m1 stop
Multiple Airlines Logo
9:32 pm - 8:27 pm
STL
-
PDX
24h 55m2 stops
$223Multiple Airlines
Sat, Feb 14 - Tue, Feb 17
Alaska Airlines Logo
7:00 am - 1:11 pm
PDX
-
ORD
4h 11mnonstop
Alaska Airlines Logo
5:29 pm - 10:41 pm
ORD
-
PDX
7h 12m1 stop
$227Alaska Airlines
Sat, Jan 24 - Sat, Jan 31
Southwest Logo
6:00 am - 11:55 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
9:45 am - 4:40 pm
MDW
-
PDX
8h 55m2 stops
$227Southwest
Sat, Jan 24 - Sat, Jan 31
Southwest Logo
12:05 pm - 10:35 pm
PDX
-
ORD
8h 30m1 stop
Southwest Logo
2:15 pm - 8:40 pm
ORD
-
PDX
8h 25m1 stop
$228Southwest
Thu, May 21 - Wed, May 27
Alaska Airlines Logo
11:18 am - 5:06 pm
PDX
-
STL
3h 48mnonstop
Alaska Airlines Logo
6:20 pm - 8:37 pm
STL
-
PDX
4h 17mnonstop
$229Alaska Airlines
Sat, Jan 17 - Tue, Jan 20
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
3:53 pm - 10:53 pm
ORD
-
PDX
9h 00m1 stop
$232United Airlines
Wed, Jan 28 - Fri, Jan 30
United Airlines Logo
1:24 pm - 9:15 pm
PDX
-
ORD
5h 51m1 stop
United Airlines Logo
9:10 am - 11:57 am
ORD
-
PDX
4h 47mnonstop
$233United Airlines
Wed, Feb 4 - Sat, Feb 7
American Airlines Logo
5:14 am - 9:43 pm
PDX
-
PIA
14h 29m2 stops
American Airlines Logo
4:20 pm - 10:11 pm
PIA
-
PDX
7h 51m1 stop
$368American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
11:59 pm - 10:15 am
PDX
-
EVV
8h 16m1 stop
American Airlines Logo
4:13 pm - 11:37 pm
EVV
-
PDX
9h 24m1 stop
$379American Airlines
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Portland found in the last 72 hours was to Chicago, at $198 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 $233.

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 $341, 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 August, when tickets cost $291 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $451 and $422 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 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, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Portland to St. Louis

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 $320 on average. Morning departures are around 52% 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 $486.

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 $181 one-way - $348 round-trip

Reviews of the 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 11555 reviews
7.0Entertainment
8.1Boarding
7.8Comfort
7.1Food
8.5Crew
Airline reviews

Coke zero offered...good. The proptness of flight was late. This has been a everytime thing for my last 9 flights. And is putting alot of pressure on my connecting flights. Not a bit punctual. I am always early, but Ak. Airlines is not. And people i happen fly beside, parrot the same thing. The baggage delivery to baggage claim, is not prompt. Its slowwwww. The seats are poorly padded, very crowd. We need more room, not padding the airlines bottom line. Its like a cattle car. More leg room, more side to side room. And attendants need upgrade of verbal skills. I have been faithful to Ak. A., but it will change if changes are not made. Not the only planes in the sky.

4.0 OkayJim, Dec 2025
PDX - ANC
Read more Alaska Airlines reviews

Coke zero offered...good. The proptness of flight was late. This has been a everytime thing for my last 9 flights. And is putting alot of pressure on my connecting flights. Not a bit punctual. I am always early, but Ak. Airlines is not. And people i happen fly beside, parrot the same thing. The baggage delivery to baggage claim, is not prompt. Its slowwwww. The seats are poorly padded, very crowd. We need more room, not padding the airlines bottom line. Its like a cattle car. More leg room, more side to side room. And attendants need upgrade of verbal skills. I have been faithful to Ak. A., but it will change if changes are not made. Not the only planes in the sky.

Everything was great except for one piece of our luggage was severely damaged and crushed. There were no agents available at baggage claim and the hold time on the phone was over 3 hours. So therefore we were unable to file a complaint. We will be speaking to Alaska Airlines about replacing our luggage when we check in for our return flight.

Great airline. Sat next to a really big person tho

I always choose Alaska when I can. Every thing seems to run more efficiently with them.

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

I would have liked if the flight existed. To be fair the federal government canceled it. But, since it WAS canceled, I would have liked it if Alaska Airlines had moved a finger to assist me rather then abandoning me with my luggage, unable to check it, for 14 hours in Portland. So federal regulations forbid them from storing my bag? Then at least help me find storage or SOMETHING.

It was all good, no delays which was a worry. All great

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

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.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

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.

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.

I had to cancel the flight because with a 3 hour delay for 'unexpected maintenance' in getting to LAX, I couldn't connect to an overseas flight that I had booked on Scandinavian Air.

The flight was CANCELED!!! Can’t get much more “poor” than that. I had to switch to American Airlines, add another layover and got home in Honolulu 4 hours later than I was supposed to be home. One bright spot was Josh with Alaska Airlines at SFO. He got me on a United Flight that got me home a few hours before I would have. Without him I would have gotten home almost 7 hours after my originally scheduled flight.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

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 was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Everything you need to know for your flight from Portland to Illinois

Information on your arrival and departure airports