$60 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 3/6. 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.
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$214
Moline
Moline1 stop$305
Peoria
Peoria1 stop$309
Bloomington
Bloomington1 stop$357
Champaign
Champaign1 stop$388
St. Louis
St. Louis1 stop$183
Paducah
Paducah1 stop$495
Chicago
Chicagononstop$214
Moline
Moline1 stop$305
Peoria
Peoria1 stop$309
Bloomington
Bloomington1 stop$357
Champaign
Champaign1 stop$388
St. Louis
St. Louis1 stop$183
Paducah
Paducah1 stop$495

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

Fri, Mar 6 - Sun, Mar 8
Frontier Logo
12:04 pm - 9:49 am
PDX
-
STL
19h 45m
1 stop
Frontier Logo
6:19 pm - 9:13 am
STL
-
PDX
16h 54m
1 stop
$183Frontier
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
11:35 pm - 5:32 am
PDX
-
ORD
3h 57mnonstop
American Airlines Logo
9:46 pm - 12:17 am
ORD
-
PDX
4h 31mnonstop
$214American Airlines
Tue, Mar 3 - Sat, Mar 7
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 12m
1 stop
$217Alaska Airlines
Tue, Apr 14 - Sat, Apr 18
Southwest Logo
5:40 am - 11:35 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:00 am - 10:15 am
MDW
-
PDX
6h 15m
1 stop
$217Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:00 pm - 5:25 am
PDX
-
MDW
10h 25m
1 stop
Southwest Logo
8:50 pm - 11:10 pm
MDW
-
PDX
4h 20mnonstop
$223Southwest
Wed, Mar 4 - Wed, Mar 11
Delta Logo
12:40 am - 9:06 am
PDX
-
MDW
6h 26m
1 stop
Delta Logo
2:05 pm - 8:25 pm
MDW
-
PDX
8h 20m
1 stop
$227Delta
Sat, May 2 - Wed, May 6
United Airlines Logo
2:24 pm - 10:59 pm
PDX
-
STL
6h 35m
1 stop
United Airlines Logo
5:59 pm - 10:54 pm
STL
-
PDX
6h 55m
1 stop
$232United Airlines
Mon, Feb 16 - Tue, Feb 24
Delta Logo
12:40 am - 9:06 am
PDX
-
MDW
6h 26m
1 stop
Delta Logo
1:49 pm - 8:30 pm
MDW
-
PDX
8h 41m
1 stop
$234Delta
Tue, Mar 3 - Tue, Mar 10
United Airlines Logo
12:57 pm - 10:14 pm
PDX
-
STL
7h 17m
1 stop
United Airlines Logo
6:51 am - 12:33 pm
STL
-
PDX
7h 42m
1 stop
$237United Airlines
Sun, May 24 - Sat, May 30
Alaska Airlines Logo
5:00 am - 3:50 pm
PDX
-
STL
8h 50m
1 stop
Alaska Airlines Logo
6:20 pm - 8:37 pm
STL
-
PDX
4h 17mnonstop
$239Alaska 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 $217 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 $217.

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 $319, 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 $289 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $409 and $398 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 Monday. On your return trip to Portland, you should consider flying back on a Tuesday, 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 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$60
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 4% 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 $314 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 $478.

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 $166 one-way - $318 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 11834 reviews
7.0Entertainment
7.1Food
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

Alaska used to be a top notch airline. With it's growth it is now in line with the big airlines. Not bad, not great.

6.0 GoodJack, Feb 2026
PDX - SFO
Read more Alaska Airlines reviews

Alaska used to be a top notch airline. With it's growth it is now in line with the big airlines. Not bad, not great.

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

Everything from the time I booked my flight through to the end when I got home was smooth and wonderful. Service was great, the flight attendants were attentive and there were no outstanding delays.

Delayed and no entertainment? I also forgot my headphones and immediately reported it and have not heard back yet.

The crew was very friendly. Boarding was quick and efficient.

You need categories to note when food and entertainment are not available. Alaska's system would not update flight info on the board for this flight, so there was some confusion after deplaning from the previous flight as to which gate and depart time were accurate for this flight.

we waited for 50 minutes to check a bag and missed a flight. do better.

The flight crew was very professional and pleasant. Our flight was delayed 3 hours, but Kayak informed me in advance

Before I even boarded this old white man , a fat Samoan lady, and a short brown guy were at the desk. They asked if we could have 15 volunteers to get free checked bags cause it was a full flight. I waited in line, I got up to the short brown guy and he asked for my boarding pass and I showed him, he said that he can’t check my bag because I wasn’t given a seat yet. So he had me go to the next line with the old white guy, but before I switched lines I asked him, well if I go to that line, will I be able to check my bag so I waited in line and he said yeah, it doesn’t matter , I’m good. So I switch lines and wait in the line of the old white man, with every guest before me he was very sweet , making small talk, smiling and had great eye contact( all of the people he was talking to was white) I come up and he doesn’t look at me , then says I’ll be right with you, I wait for him to initiate and when he does he’s like what’s up? I was like the man next to you told me I needed to get checked in before I can check my bag. He’s like what’s your last name and I say Valenzuela , and he said we’re not there yet, all while not smiling, no eye contact like he was with the other guests. He said we’re will call you when I get to you. So I go sit down and I’m sitting down for less than a minute and he calls me and someone else. I go up and say Valenzuela and he’s like who are you and I’m like Valenzuela , he’s like hmm and says don’t go anywhere and calls someone else. I finally get my seat and I go back to the short brown man and ask if I can check my bag and he said there isn’t any room available and I was like? Wait you told me and then the fat Samoan lady said yeah we don’t need anymore bags thank you. I was dumbfounded and just walked away. So rude. Terrible experience and terrible communication on their end.

The flight was delayed, but once it arrived everything moved right along.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

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.

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

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

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

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

Information on your arrival and departure airports