$61 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 11/4. 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

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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$224
Moline
Moline1 stop$251
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$379
Champaign
Champaign1 stop$503
Springfield
Springfield1 stop$453
St. Louis
St. Louis1 stop$249
Marion
Marion1 stop$2,388
Chicago
Chicagononstop$224
Moline
Moline1 stop$251
Peoria
Peoria1 stop$289
Bloomington
Bloomington1 stop$379
Champaign
Champaign1 stop$503
Springfield
Springfield1 stop$453
St. Louis
St. Louis1 stop$249
Marion
Marion1 stop$2,388

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, Nov 19 - Fri, Nov 28
Alaska Airlines Logo
11:00 pm - 5:01 amPDX-ORD
4h 01mnonstop
Alaska Airlines Logo
7:00 am - 9:39 amORD-PDX
4h 39mnonstop
$224Alaska Airlines
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Sun, Dec 14 - Thu, Jan 8
Frontier Logo
7:26 pm - 8:17 pmPDX-ORD
22h 51m1 stop
Frontier Logo
10:01 pm - 10:34 amORD-PDX
14h 33m1 stop
$225Frontier
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Fri, Dec 5 - Sun, Dec 7
Southwest Logo
6:15 am - 12:10 pmPDX-MDW
3h 55mnonstop
Southwest Logo
9:50 pm - 12:20 amMDW-PDX
4h 30mnonstop
$227Southwest
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Sun, Dec 14 - Thu, Dec 18
Delta Logo
7:30 pm - 8:40 amPDX-ORD
11h 10m2 stops
Delta Logo
7:20 am - 12:40 pmORD-PDX
7h 20m1 stop
$228Delta
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Fri, Dec 5 - Mon, Dec 8
Delta Logo
5:30 am - 6:18 pmPDX-MDW
10h 48m2 stops
Delta Logo
10:36 am - 7:35 pmMDW-PDX
10h 59m1 stop
$228Delta
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
6:15 am - 12:10 pmPDX-MDW
3h 55mnonstop
Southwest Logo
3:15 pm - 10:30 pmMDW-PDX
9h 15m1 stop
$230Southwest
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Wed, Dec 10 - Sat, Dec 13
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
United Airlines Logo
9:05 am - 11:48 amORD-PDX
4h 43mnonstop
$231United Airlines
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Sat, Dec 6 - Sat, Dec 13
United Airlines Logo
10:50 am - 4:52 pmPDX-ORD
4h 02mnonstop
United Airlines Logo
9:05 am - 11:48 amORD-PDX
4h 43mnonstop
$232United Airlines
Find Deal
Mon, Dec 15 - Tue, Dec 16
American Airlines Logo
1:28 pm - 7:46 pmPDX-ORD
4h 18mnonstop
American Airlines Logo
8:10 am - 10:47 amORD-PDX
4h 37mnonstop
$241American Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 12
American Airlines Logo
11:43 am - 5:55 pmPDX-ORD
4h 12mnonstop
American Airlines Logo
8:14 am - 10:48 amORD-PDX
4h 34mnonstop
$243American 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 $210 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 $244.

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 $326, 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 $293 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $451 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 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 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$61
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 22% 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 $315 on average. Morning departures are around 57% 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 $495.

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 $173 one-way - $331 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 11150 reviews
7.1Food
7.8Comfort
8.5Crew
8.1Boarding
7.0Entertainment
Airline reviews

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

8.0 ExcellentJ, Oct 2025PDX - SFO
Read more Alaska Airlines reviews

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

One disappointment. There was a gate change from B8 to B10, they had announced it maybe 20 minutes before the boarding time, possibly less. I didn’t hear the announcement as I was listening to music on my head phones at B8. At the boarding time, I got up and asked the gal at the B8 boarding desk, why the destination sign had not changed and if the flight was delayed as there was no plane behind her through the window, she said that perhaps the flight was delayed and the screen will probably update in -5 minutes ( she apparently didn’t know the boarding gate was changed ( 2 down from our location) I put my headphones on and went back to sit down . Just before the B10 door closed, I got a phone call asking me if I was still taking the flight, I said. “Yes” but I was at the gate stated on my ticket B8, then I was informed of the gate change, I got up and ran to the gate, and down the hallway to the jet ramp. I was the last to board!! Very frustrating . I was shocked that I got no emails or text messages from Alaska informing me of a last minute change!!

The crew was the best I’ve ever had HOWEVER when we arrived in Salt Lake City there were no Alaskan Airline employees to be found so we weren’t able to leave the plane until ANOTHER airline took pity on us. How could that possible happen?

The pilot performed the smoothest landing I’ve ever experienced. What a light touch. And I’m an avid traveler!

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

I received several emails about my 3:10 flight. When I showed up to the airport at 12:30 to check my bags I was told the flight was actually at 1 pm. They grudgingly rebooked me for a flight at 5:22 to Vegas to get a connecting to LAX. I did find the gate for my original 3:10 flight but they were booked. I proceeded to receive status updates and gate change information for the 3:10 flight, even though I was apparently never supposed to be on that flight

My flight was delayed three hours and then cancelled. The gate agent proceeded to rebook me in a middle seat without telling me and I was placed between two large individuals who did not fit in their own seats and instead took up most of mine. It was an awful experience.

The food options were limited and very specific. Some type of entertainment option for a 4.5 hour flight would have been nice.

Flight was smooth and comfortable. We were able to check a bag at counter due to full flight and boarded with an earlier group. We were there very early and didn’t hear the gate change just noticed our flight was no longer displayed st the gate. There were two other flights with gate shuffles - may be unavoidable but not desirable. First time I had to print my own luggage tag and attach at arrival. Not a fan of that process.

The crew was EXTREMELY helpful And sweet and the flight was smooth!

I received an email from Kayak with confirmation number for Hawaiian and another for Alaska. I received emails from Kayak for both my outbound and return flight to say "time to check in." Despite trying each number (Hawaiian and Alaska), I could not check in for outbound or return. It was then confusing at the airport - I hda "no place to go" to figure out how to check in. All the kiosks are marked "scan bag,etc." I wandered around with no agent to talk to. That was a bit stressful. Either Kayak, or airline, needed better communication on what to expect and to do.

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

When I purchased my ticket, it said i was flying with Hawaii airlines. Which is now operated by Alaska. Naturally I went to check in with Hawaii airlines once at the airport. However, there was no one at the desk until 7 am and their kiosk couldn’t find my tickets. I went over to Alaska and they said they couldn’t help me and to wait for Hawaii. My flight left at 7:15 so I didn’t have time to wait. They even told me to ask United which was next to the Hawaii desk what time Hawaii opened. I called the Hawaii airlines number and the operator told me to ask Alaska for help since my flight was operated by Alaska. So I went back and almost got brushed off again and sent to Hawaii. The Alaska desk attendant told me to check in at their kiosk but it didn’t work. I ran over to an older lady who was helping check bags and asked for help printing my boarding passes. Thankful she was able to do it right away! This whole debacle took a little over an hour. I wish there was better communication and knowledge between the two airlines because it could have been easily handled if everyone between the two airlines was on the same page. Once I ran through the airport to get to my gate, we were greeted with a smile and they seemed glad we made our flight! We were the last to board and barely made it. After the headache our flight was great! No complaints there.

Biggest issue: awfully narrow seats, + not a lot of leg room. Other than that, everything was good. Cabin crew seemed like very nice people.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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 a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

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