$87 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 9/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$176
Moline
Moline1 stop$335
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$507
Champaign
Champaign1 stop$506
Springfield
Springfield2 stops$422
St. Louis
St. Louis1 stop$229
Chicago
Chicago1 stop$176
Moline
Moline1 stop$335
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$507
Champaign
Champaign1 stop$506
Springfield
Springfield2 stops$422
St. Louis
St. Louis1 stop$229

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

Wed, Sep 10 - Sun, Sep 14
 Logo
12:07 pm - 9:32 pmPDX-ORD
7h 25m1 stop
 Logo
6:00 am - 12:12 amORD-PDX
20h 12m1 stop
Fri, Sep 26 - Mon, Sep 29
Frontier Logo
6:05 am - 3:53 pmPDX-MDW
7h 48m1 stop
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
$177Frontier
Find Deal
Fri, Oct 31 - Sun, Nov 2
Southwest Logo
2:05 pm - 10:35 pmPDX-MDW
6h 30m1 stop
Southwest Logo
9:50 pm - 12:20 amMDW-PDX
4h 30mnonstop
$224Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30
United Airlines Logo
8:30 am - 2:38 pmPDX-ORD
4h 08mnonstop
United Airlines Logo
7:55 pm - 10:30 pmORD-PDX
4h 35mnonstop
$227United Airlines
Find Deal
Wed, Oct 29 - Sat, Nov 1
Southwest Logo
1:25 pm - 7:20 pmPDX-MDW
3h 55mnonstop
Southwest Logo
3:45 pm - 6:05 pmMDW-PDX
4h 20mnonstop
$227Southwest
Find Deal
Tue, Sep 16 - Wed, Oct 1
American Airlines Logo
1:40 pm - 7:49 pmPDX-ORD
4h 09mnonstop
American Airlines Logo
7:25 am - 9:47 amORD-PDX
4h 22mnonstop
$229American Airlines
Find Deal
Tue, Sep 16 - Sat, Sep 20
American Airlines Logo
11:18 am - 5:28 pmPDX-ORD
4h 10mnonstop
American Airlines Logo
8:05 am - 10:28 amORD-PDX
4h 23mnonstop
$231American Airlines
Find Deal
Fri, Sep 26 - Sat, Sep 27
Alaska Airlines Logo
10:55 pm - 5:00 amPDX-ORD
4h 05mnonstop
Alaska Airlines Logo
7:00 am - 9:25 amORD-PDX
4h 25mnonstop
$232Alaska Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27
United Airlines Logo
5:00 am - 12:43 pmPDX-STL
5h 43m1 stop
United Airlines Logo
1:40 pm - 8:50 pmSTL-PDX
9h 10m2 stops
$234United Airlines
Find Deal
Sat, Feb 21 - Wed, Feb 25
Alaska Airlines Logo
7:00 am - 5:34 pmPDX-MLI
8h 34m1 stop
Alaska Airlines Logo
11:32 am - 4:39 pmMLI-PDX
7h 07m1 stop
$379Alaska Airlines
Find Deal
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 $139 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 $200.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $692 on average.

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 $281 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $448 and $420 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 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$87
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 13% 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 $309 on average. Morning departures are around 64% 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 $506.

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 $174 one-way - $321 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 10000 reviews
8.5Crew
7.8Comfort
7.1Food
7.0Entertainment
8.1Boarding
Airline reviews

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

8.0 ExcellentAnonymous, Aug 2025PDX - SMF
Read more Alaska Airlines reviews

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

I booked a round trip. I ordered a lunch going and a lunch for the return but got both lunches going. Could have been my error. Both lunches were good.

Well the flight being delayed multiple time really was frustrating. But the crew and flight was good.

generally good. No snacks or drinks on the flight 3379 from Portland to San Jose, CA. Sad.

Everything except for the lack of a choice of the snack provided was great.

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

First time flying with Alaska, and it went great. Thank you for a great experience flying to PDX.

There was a very drunk man behind me who kept talking loudly to no one in particular. He was slurring his words and at times he didn’t know where we were going or whether or not we landed. He was also loudly using a lot of profanity. The attendants didn’t seem to notice or care and in fact continued to serve him alcohol. He was allowed to purchase 4 little bottles.

We did not realize there wasn't any food apart from a small packet of pretzels - I dropped one and nearly cried.

I recently flew with Alaska Airlines on a trip to Oregon and had a very frustrating experience that I hope the airline can learn from. I purchased upgraded seats with extra legroom for my flight, paying the additional fees for the comfort and space. During my trip planning, I called customer service to inquire about their pet travel policies and conditions, as I was considering bringing my dogs. However, I ultimately decided NOT to bring my pets and never authorized or confirmed any pet travel arrangements. Despite this, Alaska Airlines took it upon themselves to change my seat assignment without any notification or contact. When I arrived for my flight, I discovered that my paid upgrade had been downgraded to a regular seat - presumably because they assumed I would be traveling with pets based on my inquiry call. I hope Alaska Airlines will improve their communication processes and ensure that customer inquiries don’t automatically trigger booking changes without explicit customer authorization. Better staff training on distinguishing between inquiries and actual bookings would prevent this type of situation in the future. While I appreciate that the airline tries to accommodate pet travelers, making assumptions and changes without customer consent is poor service that needs to be addressed.

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.