$126 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 9/18. 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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Flight Deals

Cheap Flights from Portland to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$322
Moline
Moline1 stop$320
Peoria
Peoria1 stop$331
Bloomington
Bloomington1 stop$349
Champaign
Champaign1 stop$338
Springfield
Springfield1 stop$495
St. Louis
St. Louis1 stop$240
Marion
Marion1 stop$532
Paducah
Paducah1 stop$438
Chicago
Chicago1 stop$322
Moline
Moline1 stop$320
Peoria
Peoria1 stop$331
Bloomington
Bloomington1 stop$349
Champaign
Champaign1 stop$338
Springfield
Springfield1 stop$495
St. Louis
St. Louis1 stop$240
Marion
Marion1 stop$532
Paducah
Paducah1 stop$438

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, Sep 11 - Sun, Sep 13
Frontier Logo
9:34 pm - 11:51 am
PDX
-
STL
12h 17m
1 stop
Frontier Logo
12:46 pm - 8:39 pm
STL
-
PDX
9h 53m
1 stop
$240Frontier
Tue, Jul 14 - Tue, Jul 21
Frontier Logo
5:16 pm - 7:23 pm
PDX
-
STL
24h 07m
1 stop
Frontier Logo
8:08 pm - 4:36 pm
STL
-
PDX
22h 28m
1 stop
$250Frontier
Fri, Jul 17 - Wed, Jul 22
American Airlines Logo
12:45 am - 10:39 am
PDX
-
MLI
7h 54m
1 stop
American Airlines Logo
6:50 pm - 12:50 am
MLI
-
PDX
8h 00m
1 stop
$320American Airlines
Wed, Jul 15 - Wed, Jul 22
United Airlines Logo
2:25 pm - 8:38 pm
PDX
-
ORD
4h 13mnonstop
United Airlines Logo
7:55 pm - 10:30 pm
ORD
-
PDX
4h 35mnonstop
$325United Airlines
Sat, Jul 18 - Sat, Jul 25
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
PDX
4h 25mnonstop
$325Southwest
Thu, Oct 8 - Wed, Oct 14
Delta Logo
6:04 am - 4:22 pm
PDX
-
MLI
8h 18m
1 stop
Delta Logo
11:00 am - 9:53 pm
MLI
-
PDX
12h 53m
2 stops
$325Delta
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
1:28 pm - 11:06 pm
PDX
-
PIA
7h 38m
1 stop
American Airlines Logo
6:30 pm - 10:59 pm
PIA
-
PDX
6h 29m
1 stop
$331American Airlines
Sat, Jul 18 - Sat, Jul 25
Southwest Logo
7:45 pm - 5:00 am
PDX
-
MDW
7h 15m
1 stop
Southwest Logo
8:25 pm - 10:50 pm
MDW
-
PDX
4h 25mnonstop
$335Southwest
Thu, Oct 1 - Tue, Oct 6
United Airlines Logo
11:30 pm - 10:12 am
PDX
-
MLI
8h 42m
1 stop
United Airlines Logo
6:32 am - 11:33 am
MLI
-
PDX
7h 01m
1 stop
$342United Airlines
Tue, Aug 4 - Tue, Aug 18
Delta Logo
12:35 am - 8:39 am
PDX
-
MDW
6h 04m
1 stop
Delta Logo
1:51 pm - 8:17 pm
MDW
-
PDX
8h 26m
1 stop
$345Delta
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 $268 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 $315.

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 $360 on average. Morning departures are around 32% 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 $474.

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 $390, 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 October and August, when the average cost of round-trip tickets is $708 and $694 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 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 51% 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$126
Best time to beat the crowds with an average 19% drop 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 $219 one-way - $398 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 12564 reviews
7.8Comfort
8.1Boarding
7.0Entertainment
7.0Food
8.5Crew
Airline reviews

Although delayed an hour, the gate attendants kept us notified and the rest of the trip went off with no issues.

8.0 ExcellentLisa, Jun 2026
PDX - DEN
Read more Alaska Airlines reviews

Although delayed an hour, the gate attendants kept us notified and the rest of the trip went off with no issues.

We showed up to our gate less than 15 minutes after boarding started and they wouldn’t let us in. It was still 15 minutes even before take off so we’re weren’t even late to the flight.

When I checked in with full service, requesting a wheelchair, as I had asked for ahead of time, the customer service agent said “wait over there, nothing more. I waited in the designated space for about 40 minutes before learning from another passenger that I needed to check in again at a specific assistance desk. I was early, so I made it on time to my flight. Your agent should not assume I knew anything, which I didn’t. This was all new, in a recently remodeled space. New to me, anyway.

Great trip. No complaints. Impressed with the crew’s response to various challenges pre-boarding.

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.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

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.

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

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.

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

Information on your arrival and departure airports