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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 6/6. 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
Sat 6/15
Sat 6/22

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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$58
Moline
Moline1 stop$421
St. Louis
St. Louis1 stop$286

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 16% 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 $205 one-way - $381 round-trip
  • Morning departure is around 14% 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 10673 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

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.

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

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!!

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.

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

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 😕

Book cheap flights from Portland to Illinois

Recent round-trip flight deals

8/6Tue
nonstopFrontier
2h 43mPWM-ORD
8/13Tue
nonstopFrontier
2h 21mORD-PWM
$58
6/13Thu
nonstopFrontier
2h 43mPWM-ORD
6/18Tue
nonstopFrontier
2h 20mORD-PWM
$59
8/4Sun
1 stopDelta
4h 18mPWM-ORD
8/13Tue
1 stopDelta
6h 39mORD-PWM
$216
7/14Sun
1 stopDelta
4h 01mPWM-MDW
7/23Tue
1 stopDelta
4h 41mMDW-PWM
$216
6/13Thu
1 stopJetBlue
8h 58mPWM-ORD
6/18Tue
1 stopJetBlue
7h 24mORD-PWM
$224
7/4Thu
nonstopAmerican Airlines
2h 53mPWM-ORD
7/8Mon
nonstopAmerican Airlines
2h 29mORD-PWM
$239
8/6Tue
1 stopJetBlue
7h 47mPWM-ORD
8/14Wed
1 stopJetBlue
6h 49mORD-PWM
$244
7/12Fri
nonstopAmerican Airlines
2h 48mPWM-ORD
7/16Tue
1 stopAmerican Airlines
6h 08mORD-PWM
$248
7/16Tue
nonstopUnited Airlines
2h 49mPWM-ORD
7/29Mon
nonstopUnited Airlines
2h 28mORD-PWM
$267
9/5Thu
nonstopUnited Airlines
2h 48mPWM-ORD
9/7Sat
nonstopUnited Airlines
2h 31mORD-PWM
$309

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Recent one-way flight deals

6/6Thu
nonstopFrontier
2h 43mPWM-ORD
$40
6/20Thu
nonstopFrontier
2h 43mPWM-ORD
$49
5/21Tue
nonstopFrontier
2h 46mPWM-ORD
$51
7/17Wed
nonstopUnited Airlines
2h 49mPWM-ORD
$105
6/11Tue
1 stopDelta
6h 20mPWM-ORD
$108
7/21Sun
1 stopDelta
4h 18mPWM-ORD
$118
7/17Wed
1 stopJetBlue
7h 47mPWM-ORD
$122
6/3Mon
nonstopUnited Airlines
2h 49mPWM-ORD
$130
9/16Mon
nonstopAmerican Airlines
2h 50mPWM-ORD
$144
8/2Fri
nonstopAmerican Airlines
2h 48mPWM-ORD
$145

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Last minute flights from Portland to Illinois

Last minute flight, train and bus deals

5/21Tue
multi-stopFrontier
9h 48mPWM-ORD
6/11Tue
nonstopFrontier
2h 20mORD-PWM
$148
5/21Tue
multi-stopFrontier
9h 48mPWM-ORD
5/23Thu
nonstopFrontier
2h 20mORD-PWM
$174
5/21Tue
multi-stopAmerican Airlines
7h 52mPWM-ORD
6/11Tue
multi-stopAmerican Airlines
5h 40mORD-PWM
$500
5/21Tue
multi-stopUnited Airlines
16h 46mPWM-ORD
6/11Tue
multi-stopUnited Airlines
6h 58mORD-PWM
$543
5/21Tue
multi-stopDelta
10h 20mPWM-ORD
6/11Tue
multi-stopDelta
8h 35mORD-PWM
$582
5/21Tue
multi-stopUnited Airlines
6h 12mPWM-ORD
5/26Sun
multi-stopUnited Airlines
6h 45mORD-PWM
$593
5/18Sat
multi-stopDelta
5h 19mPWM-STL
5/19Sun
multi-stopDelta
8h 06mSTL-PWM
$644
5/17Fri
multi-stopAmerican Airlines
5h 51mPWM-ORD
5/19Sun
multi-stopAmerican Airlines
8h 04mORD-PWM
$675
5/18Sat
multi-stop
25h 42mPWM-STL
5/19Sun
multi-stop
13h 39mSTL-PWM
$787
5/18Sat
multi-stop
25h 42mPWM-STL
5/19Sun
multi-stop
20h 43mSTL-PWM
$800

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Portland - Illinois Flights

Departure:

Portland (PWM)United States

Return flight deals:

Illinois - Portland

Cabin classes:

$1,039
$1,468
$1,051
$158