$180 Find Cheap Flights from Portland to Illinois - Compare and Save

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Cheap Flights from Portland to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicago2 stops$347
Moline
Moline1 stop$469
Chicago
Chicago2 stops$347
Moline
Moline1 stop$469
Booking Insights

Price, demand and travel trends for Portland to Illinois flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Portland to Illinois recently?

The cheapest fares from Portland to Illinois on KAYAK in the last week were to Chicago O'Hare Intl (ORD) from $347 round-trip and to Chicago Midway (MDW) from $369 round-trip.

How do fares into airports in Illinois compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Illinois from Portland are:

• Bloomington-Normal (BMI) (avg. price $334)
• Moline Quad-City (MLI) (avg. price $359)
• Chicago O'Hare Intl (ORD) (avg. price $384)

Are flights from Portland to Illinois cheaper or more expensive than last year?

Fares from Portland to Illinois are about 5% higher than they were in November last year, averaging $385 round-trip.

What's the cheapest month to fly from Portland to Illinois?

May is typically the cheapest month to fly from Portland to Illinois, with round-trip fares averaging $329. November and December are usually the most expensive, averaging $452 and $451, respectively.

How do fares from Portland to Illinois vary by day of the week?

On average, Saturday is the cheapest day to fly from Portland to Illinois and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 44% more expensive to fly on a Sunday compared to Saturday.

What's the best time of day to fly from Portland to Illinois?

It's cheapest to fly to Illinois in the afternoon with average prices of $371. The morning is the most expensive time to fly, with average prices of $396.

What's the best time to book a flight from Portland to Illinois?

Book your flights 26 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 44% compared to booking at the last minute (within 2 weeks of departure).

Key details for Portland to Illinois flights

Low season

February

Cheapest flight

$180
Beat the crowds with an average 37% drop in travelers.
The most popular month to fly with an average 25% increase in travelers.
One-way flight from Portland to Chicago O'Hare Intl Airport

Your Portland to Illinois flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Portland to Illinois?

    Fares from Portland to Illinois are around their usual level right now. A round-trip under $318 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch fare changes.

  • How much should I budget for a flight from Portland to Illinois?

    Over the past 12 months, round-trip fares from Portland to Illinois have typically cost between $318 and $482.

  • What are the main airports serving Illinois?

    Illinois has 17 airports. 93% of KAYAK users choose Chicago O'Hare Intl (ORD) as their arrival airport.

  • Which airlines fly nonstop from Portland to Illinois?

    Based on the flight schedule for the next 3 months, 2 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines

  • Which destinations in Illinois can I fly nonstop from Portland?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Portland to just one destination in Illinois: Chicago.

  • Is it cheaper to fly with a layover from Portland to Illinois?

    Yes, nonstop flights from Portland to Illinois average $387 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • New York John F Kennedy Intl (JFK) (avg. price $188)
    • New York LaGuardia (LGA) (avg. price $301)
    • Washington, D.C. Reagan-National (DCA) (avg. price $345)

  • How long is a flight from Portland to Illinois?

    Nonstop flights from Portland to Illinois take 3h 11m on average. All flights fly into Chicago O'Hare Intl (ORD).

  • Which cabin classes are available from Portland to Illinois?

    On flights from Portland to Illinois you can book Economy Class or First Class.

  • What are some popular landmarks around Illinois?

    Illinois is home to many popular sights. KAYAK travelers' favorites include:

    • Magnificent Mile
    • Grant Park
    • Soldier Field
    • River North

  • What are the earliest and latest flights from Portland to Illinois?

    The earliest nonstop flight from Portland to Illinois departs at 8:00 am and the latest leaves at 5:08 pm. Nonstop flights take about 3h 11m.

Your guide to booking Portland to Illinois flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 26 weeks before your trip. KAYAK data shows fares in this window are around 44% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in May to save some money. It's typically the cheapest month on this route, while flights in November will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Sunday flights, which are about 44% more expensive.
  • If you're watching your budget, fly into Bloomington-Normal (BMI) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Chicago, the most popular destination in Illinois. From there, it's easy to continue on to other popular spots such as Rosemont, Schaumburg and Champaign.
  • Time or money? If speed matters most, fly from Portland to Chicago O'Hare Intl (ORD). If you're after the lowest fares, Bloomington-Normal (BMI) is usually your best bet.

Reviews of the top 4 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
SouthwestOverall score based on 4220 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

2.0 MediocreKevin, Oct 2026
Read more Southwest reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

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.

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.

Requested an aisle seat at the gate and got it. The staff so friendly

Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

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.

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

I appreciate how quickly and kindly the people at the gate at DCA accommodated several of us who wanted to switch from the 6pm flight to the 5pm flight at the last minute. The flight crew was helpful to us too (dealing with luggage).

Waited on tarmac to take off for approximately 15-25 minutes. When landing, the taxi to our gate took a similar amount of time. This happened on both of my United flights.

Fine except from Chicago to moline three different gate changes and flight times

When booking, the connection times seem fine. But in reality, my two connections were cut short by the first leg being delayed due to issues at the destination (too much traffic going into SFO, ORD) and it became extremely stressful.

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

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

All good. Easy check in and boarding. Lovely flight crew

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

The now boarding notification was not updated in the app until I was actually on the plan. This si a massive fail considering my flight was delayed several times. These types of failures add stress that could be avoided since I no longer feel comfortable leaving the boarding area to get food or visit a lounge. Had I used the notification from the app, I would have missed my flight. The secondly, the process of connecting to wifi on aa flights is clunky and could be streamlined better. the copy and past process feels like MVP, and you are well beyond that stage.

Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

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.

More options for your flight from Portland to Illinois

Complete your trip to Illinois with a hotel stay or car rental