$106 Find Cheap Flights from Portland to Illinois - Compare and Save

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 8/4. 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$316
Moline
Moline1 stop$291
Peoria
Peoria1 stop$340
Bloomington
Bloomington2 stops$424
Springfield
Springfield1 stop$495
St. Louis
St. Louis1 stop$211
Paducah
Paducah1 stop$483
Chicago
Chicagononstop$316
Moline
Moline1 stop$291
Peoria
Peoria1 stop$340
Bloomington
Bloomington2 stops$424
Springfield
Springfield1 stop$495
St. Louis
St. Louis1 stop$211
Paducah
Paducah1 stop$483

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

Mon, Aug 10 - Tue, Aug 18
Delta Logo
12:35 am - 8:37 am
PDX
-
STL
6h 02m
1 stop
Delta Logo
8:00 am - 12:09 pm
STL
-
PDX
6h 09m
1 stop
$211Delta
Tue, Aug 4 - Tue, Aug 18
American Airlines Logo
11:15 pm - 8:23 am
PDX
-
STL
7h 08m
1 stop
American Airlines Logo
8:00 am - 1:52 pm
STL
-
PDX
7h 52m
1 stop
$231American Airlines
Thu, Aug 13 - Mon, Aug 17
United Airlines Logo
2:27 pm - 10:59 pm
PDX
-
STL
6h 32m
1 stop
United Airlines Logo
5:30 pm - 10:52 pm
STL
-
PDX
7h 22m
1 stop
$251United Airlines
Tue, Oct 20 - Tue, Nov 10
Southwest Logo
6:00 am - 5:45 pm
PDX
-
STL
9h 45m
2 stops
Southwest Logo
8:25 am - 1:30 pm
STL
-
PDX
7h 05m
1 stop
$258Southwest
Tue, Oct 20 - Tue, Nov 10
Southwest Logo
6:00 am - 5:45 pm
PDX
-
STL
9h 45m
2 stops
Southwest Logo
1:50 pm - 9:20 pm
STL
-
PDX
9h 30m
2 stops
$263Southwest
Tue, Aug 18 - Tue, Aug 18
Alaska Airlines Logo
7:00 am - 1:13 pm
PDX
-
ORD
4h 13mnonstop
Alaska Airlines Logo
3:43 pm - 10:25 pm
ORD
-
PDX
8h 42m
1 stop
$319Alaska Airlines
Tue, Jul 28 - Sat, Aug 1
Alaska Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
Alaska Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
$320Alaska Airlines
Wed, Jul 29 - Wed, Aug 19
Multiple Airlines Logo
5:21 pm - 8:52 pm
PDX
-
ORD
25h 31m
1 stop
Multiple Airlines Logo
2:22 pm - 4:50 pm
ORD
-
PDX
4h 28mnonstop
$323Multiple Airlines
Wed, Jul 15 - Tue, Jul 21
United Airlines Logo
11:40 pm - 5:45 am
PDX
-
ORD
4h 05mnonstop
United Airlines Logo
5:00 am - 9:47 am
ORD
-
PDX
6h 47m
1 stop
$325United Airlines
Thu, Aug 20 - Sun, Aug 23
Multiple Airlines Logo
5:42 pm - 12:23 pm
PDX
-
RFD
16h 41m
2 stops
Multiple Airlines Logo
9:35 pm - 5:24 pm
RFD
-
PDX
21h 49m
1 stop
$433Multiple 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 July.

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 5 days was to Chicago, at $310 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 5 days was $310.

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 $341 on average. Morning departures are around 38% 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 $470.

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 $380, 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 November, when tickets cost $103 (return) on average. On the other hand, the most expensive months are September and October, when the average cost of round-trip tickets is $733 and $701 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 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 18% 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.

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 $209 one-way - $386 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.
7.9
Alaska AirlinesOverall score based on 12478 reviews
7.8Comfort
7.0Entertainment
8.5Crew
7.0Food
8.1Boarding
Airline reviews

We were 35 minutes late because the caterer had not stocked the plane. Plane was fully loaded and ready to go 15 minutes before departure time. We sat there 35 minutes?

6.0 GoodTom, Jun 2026
PDX - ATL
Read more Alaska Airlines reviews

We were 35 minutes late because the caterer had not stocked the plane. Plane was fully loaded and ready to go 15 minutes before departure time. We sat there 35 minutes?

The seats are too small/crowded. It is frustrating to be forced to sit with someone who is overweight as they crown the other seat. Nothing against the person…just the airline companies who continue(over decades!)to reduce seat sizes. Americans are fat. Those of us who are not are tired of being compromised by the airline companies who don’t faces that fact and make adjustments. Maybe have “overweight seats”? Maybe give us a discount for being forced into an uncomfortable flight due to others overweightness? Please, make adjustments…be accountable. Thanks!

I flew standby with my two children and completely forgot it was Memorial Day weekend. We tried to fly from PDX to YVR. Unfortunately, after four attempts, we gave up and tried SEA instead after the holiday. The ground crew was very helpful, checking us in and accommodating us when we were finally able to get on a flight. The sad part was that they accidentally loaded one of my suitcases on the Vancouver flight without us during one of our attempts to get on a flight, even though it had a standby tag on it. I filed a report with baggage services, and thankfully, it was returned to PDX the following day. AS was in touch with us and updated us on the process of returning the luggage to the USA.

Internet was great. It was nice to watch a movie. The crew was very nice.

On this flight there wer only 25 people on board. So no one in 5 rows ahead of me and noone in 7 rows behind me. So very chill.

Considering my flight to Portland was in a broken chair that I had paid extra for, this one was great. So yeah, wonderful.

Some food or at least snacks need to be offered on long flights. I thought I had ordered food for my husband and I prior to the flight, but was told during the flight that I had not. Perhaps, if you must charge extra for food, let people order on board. We did get some food, which evidently others had decided they didn’t want onboard, but it wasn’t very good. We did like the adherence to takeoff and landing times, and the quick return of our luggage.

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

very nice blankets and comfortable seats. great service. Great flights.

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

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

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.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

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.

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

Information on your arrival and departure airports