$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 5/20. 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

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Illinois, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% 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$259
Moline
Moline1 stop$311
Chicago
Chicago1 stop$259
Moline
Moline1 stop$311

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, May 20 - Wed, May 27
American Airlines Logo
7:10 am - 1:22 pm
PWM
-
STL
7h 12m
1 stop
American Airlines Logo
6:00 am - 12:40 pm
STL
-
PWM
5h 40m
1 stop
$259American Airlines
Thu, Aug 20 - Sun, Aug 23
Delta Logo
1:35 pm - 8:17 pm
PWM
-
ORD
7h 42m
1 stop
Delta Logo
7:00 am - 1:21 pm
ORD
-
PWM
5h 21m
1 stop
$259Delta
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
5:45 am - 11:50 am
PWM
-
MDW
7h 05m
2 stops
Southwest Logo
7:40 am - 2:15 pm
MDW
-
PWM
5h 35m
1 stop
$259Southwest
Tue, May 19 - Thu, May 21
United Airlines Logo
6:00 am - 7:56 am
PWM
-
ORD
2h 56mnonstop
United Airlines Logo
4:00 pm - 11:51 pm
ORD
-
PWM
6h 51m
1 stop
$263United Airlines
Thu, Aug 20 - Sun, Aug 23
Delta Logo
6:30 am - 4:45 pm
PWM
-
ORD
11h 15m
2 stops
Delta Logo
7:00 am - 1:21 pm
ORD
-
PWM
5h 21m
1 stop
$264Delta
Wed, May 13 - Fri, May 15
United Airlines Logo
3:39 pm - 9:40 pm
PWM
-
ORD
7h 01m
1 stop
United Airlines Logo
5:56 pm - 9:19 pm
ORD
-
PWM
2h 23mnonstop
$268United Airlines
Sat, Jun 6 - Sun, Jun 7
Southwest Logo
3:55 pm - 5:40 pm
PWM
-
MDW
2h 45mnonstop
Southwest Logo
7:55 pm - 11:10 pm
MDW
-
PWM
2h 15mnonstop
$269Southwest
Fri, May 22 - Mon, May 25
United Airlines Logo
4:56 pm - 6:56 pm
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
6:18 pm - 9:51 pm
ORD
-
PWM
2h 33mnonstop
$269United Airlines
Wed, May 13 - Fri, May 15
American Airlines Logo
6:01 pm - 8:14 pm
PWM
-
ORD
3h 13mnonstop
American Airlines Logo
7:44 pm - 11:22 pm
ORD
-
PWM
2h 38mnonstop
$270American Airlines
Sun, May 24 - Wed, May 27
American Airlines Logo
6:00 am - 8:11 am
PWM
-
ORD
3h 11mnonstop
American Airlines Logo
8:11 am - 11:46 am
ORD
-
PWM
2h 35mnonstop
$271American 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, Maine 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, Maine to Illinois departing in August.

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 $269 round-trip. The most popular route is from Portland (PWM) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $269.

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 afternoon, when round-trip flights cost $393 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally at night, which is peak travel time and where the average cost of a ticket is $514.

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 $360, 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 May, when tickets cost $279 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $420 and $401 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.

For Portland to Illinois, Thursday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Illinois back to Portland, the best deals are generally found on Tuesday, with Thursday being the most expensive.

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 3 weeks before departure, which saves you about 28% 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$87
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Portland to Chicago O'Hare Airport

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 $181 one-way - $417 round-trip; Chicago $183 one-way - $367 round-trip

Reviews of the top 3 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 4327 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

10.0 ExcellentJasmine, Apr 2026
LGB - HNL
Read more Southwest reviews

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

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.

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.

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.

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