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Find cheap flights from Portland to Illinois from $40

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 6/25. 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
0 bags
Fri 6/7
Fri 6/14

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Best Illinois Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicagononstop$79
Moline
Moline1 stop$435
St. Louis
St. Louis1 stop$284

Good to know

Low season

January

High season

October

Cheapest flight

$40
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 17% 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 to Illinois from Portland 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 to Illinois with an airline and back to Portland 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 to Illinois from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $227 one-way - $387 round-trip
  • Morning departure is around 25% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Portland to Illinois

 
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
DeltaOverall score based on 10789 reviews
7.9Comfort
8.6Crew
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Everything was good except for deplaning in NY. Took way too long!!

Jet Blue keeps getting iit wrong. 4 hour mechanical delay followed by terrible boarding experience. This is my third horrific jet blue flight in 2024. I am going to try to avoid this loser in the sky

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

Flight was delayed by over an hour and gate checked bags took 15 minutes to be delivered to the jet bridge.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

Book cheap flights from Portland to Illinois

Recent round-trip flight deals

6/11Tue
nonstopFrontier
2h 43mPWM-ORD
6/13Thu
nonstopFrontier
2h 20mORD-PWM
$79
6/11Tue
nonstopFrontier
2h 43mPWM-ORD
6/13Thu
nonstopFrontier
2h 20mORD-PWM
$81
7/2Tue
1 stopDelta
5h 04mPWM-ORD
7/9Tue
1 stopDelta
6h 28mORD-PWM
$196
7/2Tue
1 stopDelta
4h 12mPWM-MDW
7/9Tue
1 stopDelta
4h 39mMDW-PWM
$196
6/28Fri
1 stop
7h 30mPWM-ORD
6/30Sun
nonstop
2h 20mORD-PWM
$203
10/24Thu
1 stop
6h 54mPWM-ORD
10/29Tue
nonstop
2h 21mORD-PWM
$204
8/15Thu
nonstopAmerican Airlines
2h 49mPWM-ORD
8/17Sat
nonstopAmerican Airlines
2h 31mORD-PWM
$229
8/15Thu
nonstopAmerican Airlines
2h 49mPWM-ORD
8/17Sat
1 stopAmerican Airlines
5h 45mORD-PWM
$237
5/29Wed
1 stopUnited Airlines
5h 05mPWM-ORD
5/29Wed
nonstopUnited Airlines
2h 30mORD-PWM
$284
9/5Thu
nonstopUnited Airlines
2h 46mPWM-ORD
9/7Sat
nonstopUnited Airlines
2h 31mORD-PWM
$309

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Recent one-way flight deals

6/25Tue
nonstopFrontier
2h 43mPWM-ORD
$40
5/21Tue
nonstopFrontier
2h 46mPWM-ORD
$49
6/12Wed
nonstopUnited Airlines
2h 49mPWM-ORD
$95
5/30Thu
1 stopSun Country Air
20h 53mPWM-ORD
$108
6/9Sun
1 stopDelta
4h 11mPWM-MDW
$119
5/29Wed
nonstopUnited Airlines
2h 51mPWM-ORD
$120
6/13Thu
2 stopsDelta
7h 18mPWM-MDW
$124
6/8Sat
1 stopAmerican Airlines
5h 47mPWM-ORD
$128
5/23Thu
1 stopAmerican Airlines
5h 53mPWM-ORD
$138
6/30Sun
1 stopSun Country Air
6h 27mPWM-ORD
$143

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Last minute flights from Portland to Illinois

Last minute flight, train and bus deals

5/10Fri
multi-stopFrontier
10h 35mPWM-MDW
5/12Sun
multi-stopFrontier
12h 40mMDW-PWM
$334
5/11Sat
nonstopUnited Airlines
2h 59mPWM-ORD
5/12Sun
multi-stopUnited Airlines
7h 13mORD-PWM
$438
5/9Thu
multi-stopAmerican Airlines
7h 52mPWM-ORD
5/11Sat
multi-stopAmerican Airlines
8h 04mORD-PWM
$446
5/9Thu
multi-stopAmerican Airlines
7h 52mPWM-ORD
5/12Sun
multi-stopAmerican Airlines
4h 10mORD-PWM
$448
5/9Thu
multi-stopDelta
11h 20mPWM-ORD
5/11Sat
multi-stopDelta
5h 18mORD-PWM
$453
5/9Thu
multi-stopDelta
7h 35mPWM-ORD
5/11Sat
multi-stopDelta
9h 00mORD-PWM
$458
5/9Thu
nonstopUnited Airlines
3h 03mPWM-ORD
5/12Sun
multi-stopUnited Airlines
7h 13mORD-PWM
$480
5/10Fri
multi-stopAmerican Airlines
7h 55mPWM-ORD
5/12Sun
multi-stopAmerican Airlines
4h 46mORD-PWM
$486
5/10Fri
multi-stop
29h 21mPWM-ORD
5/12Sun
multi-stop
22h 40mORD-PWM
$808
5/10Fri
multi-stop
29h 21mPWM-ORD
5/12Sun
multi-stop
25h 39mORD-PWM
$885

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Portland - Illinois Flights

Departure:

Portland (PWM)United States

Return flight deals:

Illinois - Portland

Cabin classes:

$1,069
$1,290
$762
$178