$92 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 5/11. 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
Chicago1 stop$273
Moline
Moline1 stop$291
Peoria
Peoria1 stop$331
Bloomington
Bloomington1 stop$469
Champaign
Champaign1 stop$406
Springfield
Springfield1 stop$495
Marion
Marion2 stops$742
Paducah
Paducah1 stop$458
Chicago
Chicago1 stop$273
Moline
Moline1 stop$291
Peoria
Peoria1 stop$331
Bloomington
Bloomington1 stop$469
Champaign
Champaign1 stop$406
Springfield
Springfield1 stop$495
Marion
Marion2 stops$742
Paducah
Paducah1 stop$458

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

Tue, Aug 18 - Tue, Aug 25
Delta Logo
5:05 pm - 12:36 am
PDX
-
STL
5h 31m
1 stop
Delta Logo
7:30 am - 12:31 pm
STL
-
PDX
7h 01m
1 stop
$205Delta
Mon, May 11 - Thu, May 14
Frontier Logo
8:46 pm - 6:06 pm
PDX
-
STL
19h 20m
1 stop
Frontier Logo
12:36 pm - 8:51 pm
STL
-
PDX
10h 15m
1 stop
$216Frontier
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
11:30 pm - 9:35 am
PDX
-
STL
8h 05m
1 stop
Southwest Logo
5:35 am - 3:25 pm
STL
-
PDX
11h 50m
2 stops
$237Southwest
Sat, May 23 - Sat, May 30
American Airlines Logo
10:59 pm - 8:32 am
PDX
-
STL
7h 33m
1 stop
American Airlines Logo
7:20 pm - 12:50 am
STL
-
PDX
7h 30m
1 stop
$243American Airlines
Wed, Jun 3 - Sat, Jun 6
American Airlines Logo
5:49 am - 5:20 pm
PDX
-
STL
9h 31m
1 stop
American Airlines Logo
2:22 pm - 9:50 pm
STL
-
PDX
9h 28m
1 stop
$271American Airlines
Wed, May 13 - Sat, May 16
United Airlines Logo
10:55 pm - 5:02 am
PDX
-
ORD
4h 07mnonstop
United Airlines Logo
9:00 am - 11:37 am
ORD
-
PDX
4h 37mnonstop
$275United Airlines
Fri, Aug 14 - Mon, Aug 17
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
8:50 pm - 11:05 pm
MDW
-
PDX
4h 15mnonstop
$275Southwest
Sat, May 23 - Fri, May 29
United Airlines Logo
12:50 pm - 9:39 pm
PDX
-
ORD
6h 49m
1 stop
United Airlines Logo
7:05 am - 9:39 am
ORD
-
PDX
4h 34mnonstop
$276United Airlines
Sat, May 23 - Wed, May 27
Alaska Airlines Logo
10:37 am - 4:37 pm
PDX
-
STL
4h 00mnonstop
Alaska Airlines Logo
5:33 pm - 7:50 pm
STL
-
PDX
4h 17mnonstop
$277Alaska Airlines
Wed, Sep 2 - Sat, Sep 5
Alaska Airlines Logo
9:29 pm - 11:03 am
PDX
-
MLI
11h 34m
2 stops
Alaska Airlines Logo
11:33 am - 4:50 pm
MLI
-
PDX
7h 17m
1 stop
$406Alaska 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.

How much is a round-trip flight from Portland to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Illinois departing in May.

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 $274 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 $289.

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

The average price for all round-trip flights from Portland to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $315 on average. Morning departures are around 47% 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 $465.

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 $387, 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 $237 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $398 and $387 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 Monday. On your return trip to Portland, you should consider flying back on a Tuesday, 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, which saves you about 53% 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$92
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 6% 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.

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 $211 one-way - $372 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
SouthwestOverall score based on 4331 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

great experience just at the end, we got in early and there wasn't anyone at the gate for 30 min so we had to just sit on the tarmac

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

I was seating in 26A and the children in 27A and B were kicking me non-stop. They kicked me for hours nonstop and the parents refused to get off their phones or correct them. I kindly asked multiple times and got screamed at by the mom that her son is disabled. I told her I get it, but that I matter too and she is responsible for her child. He then kicked me so hard my drink spilled. Not one crew member or other passenger said or did a thing. It was so horrible.

Birding was slow. extremely slow; please do experiments on efficient plane boarding experiences; especially regarding passengers that pass their seat number…

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

I like not much people. Could tell the kids to be quiet.

I liked everything except, I left a brand new Switch 2 on the plane and talking to anybody about it is nearly impossible. I had to fill out a form and hope they get back to me in the next 2 weeks. I really hope they contact me. I saved for that thing for over a year and my son is heart broken.

Fight attendant excellent Food very good, not great Seats were stiff and uncomfortable Flight was overall very nice. Last three flights were burdened with miserably uncomfortable seats. Hard stiff no padding.

The ground crew was very good. They communicated clearly and continued updating. The flight crew was fine. The flight crew on the March 20th flight from MCI to Portland was excellent.

Flight on time. Easy boarding. Changing my seat was very easy.

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

The Honolulu Hub needs 2 to 3 times the amount of things to do as well as shuttles that transport to/from gates and terminals. Arriving from OCONUS locations; transferring to CONUS locations its a miserable experience. Fetching and re-checking bags, then returning to a gate across the airport take longer than any other large airport. If youre confused by what I mean, the process goes like this: Disembark plane Walk a mile to the main terminal Walk half a mile to baggage claim Wait 40 minutes for baggage Walk a mile to re-check-in baggage Wait 20 minutes for checking in those bags Fo back through the wrong TSA line because the signage is poor Almost miss the connecting flight because your gate is across the airport.

The checking was disaster, the crew wasn't behave well. It took us two hours to check in, after that thr line at the TSA was long, we barely make the flight. Bad airline

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

The crew were exceptionally nice and accommodating. My wife was tired after the flight from Haneda, Tokyo. They let her sleep and served her dinner later after she woke up, before we landed in PDX.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

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.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Boarding was quick and efficient. We arrived at our destination early.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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

Information on your arrival and departure airports