$133 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 9/16. 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, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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
Chicago2 stops$309
Moline
Moline1 stop$319
St. Louis
St. Louis1 stop$333
Chicago
Chicago2 stops$309
Moline
Moline1 stop$319
St. Louis
St. Louis1 stop$333

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

Thu, Aug 20 - Mon, Aug 24
Southwest Logo
10:30 am - 6:55 pm
PWM
-
MDW
9h 25m
2 stops
Southwest Logo
2:35 pm - 10:25 pm
MDW
-
PWM
6h 50m
2 stops
$309Southwest
Tue, Sep 22 - Wed, Sep 23
United Airlines Logo
6:00 am - 7:57 am
PWM
-
ORD
2h 57mnonstop
United Airlines Logo
5:50 pm - 9:23 pm
ORD
-
PWM
2h 33mnonstop
$310United Airlines
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
6:15 pm - 10:20 pm
PWM
-
MDW
5h 05m
1 stop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
$311Southwest
Tue, Sep 22 - Wed, Sep 23
American Airlines Logo
4:31 pm - 9:50 pm
PWM
-
ORD
6h 19m
1 stop
American Airlines Logo
10:13 am - 3:51 pm
ORD
-
PWM
4h 38m
1 stop
$312American Airlines
Thu, Aug 13 - Mon, Aug 17
United Airlines Logo
6:03 am - 8:00 am
PWM
-
ORD
2h 57mnonstop
United Airlines Logo
2:00 pm - 5:42 pm
ORD
-
PWM
2h 42mnonstop
$315United Airlines
Thu, Aug 6 - Mon, Aug 10
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
6:08 pm - 9:41 pm
ORD
-
PWM
2h 33mnonstop
$316United Airlines
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
7:45 am - 9:20 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
$316Southwest
Thu, Aug 20 - Sun, Aug 23
American Airlines Logo
9:08 am - 11:07 am
PWM
-
ORD
2h 59mnonstop
American Airlines Logo
8:05 am - 11:38 am
ORD
-
PWM
2h 33mnonstop
$318American Airlines
Sat, Sep 19 - Mon, Sep 21
Delta Logo
6:00 am - 12:40 pm
PWM
-
ORD
7h 40m
1 stop
Delta Logo
1:55 pm - 11:30 pm
ORD
-
PWM
8h 35m
2 stops
$322Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
6:30 am - 4:15 pm
PWM
-
MDW
10h 45m
2 stops
Delta Logo
9:24 am - 4:01 pm
MDW
-
PWM
5h 37m
1 stop
$322Delta
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 September.

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 $314 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 5 days was $314.

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 18% 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 $494.

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 1 stop layover the cheapest option at $381 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 July, when tickets cost $100 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $209 and $209 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, Wednesday 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 Saturday, with Sunday 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 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low season

February

Cheapest flight

$133
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Portland to Chicago Midway 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 $233 one-way - $399 round-trip; Chicago $232 one-way - $409 round-trip

Reviews of the top 4 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 4242 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

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

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

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

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

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

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

The head rest is too big and cannot be placed differently/removed. Causes one head to tilt forward and increase back pain

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

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.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

My overall flight got delayed by an hour (30 mins late because of late arrival and 30 mins because there was no Jet bridge available), I was supposed to land in Chicago around 9:30 PM CT, but in actual came out of plane around 10:30 PM CT. It was so frustrating and suffocating to sit in plan on runway for around 30 mins.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

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

Information on your arrival and departure airports