Find Cheap Flights from Portland to Chicago O'Hare International (PDX - ORD)

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Good to Know

Low Season:
August
Best time to beat the crowds
2%
expected price decrease
High Season:
March
Most popular time to fly
12%
expected price increase
Average Price:
$349
(avg. price over the last 2 weeks)
Good Deal:
$218
or less (round trip)

When to Book Flights from Portland to Chicago O'Hare International

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $218 or less.
The cheapest flight from Portland to Chicago O'Hare International was found 87 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be February, March and April. The cheapest month to fly is August.
Morning departure is around 24% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Portland to Chicago O'Hare International Flights

How long does a flight from Portland to Chicago O'Hare International take?
An average nonstop flight takes 3h 59m, covering a distance of 1735 miles.
How many flights are there between Portland and Chicago O'Hare International?
There are 394 (nonstop) flights between Portland and Chicago O'Hare International per week, averaging 59 per day.
Which airlines provide the cheapest flights from Portland to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on Frontier ($160), Spirit Airlines ($168) and Multiple Airlines ($180).
Do I need a passport to fly between Portland and Chicago O'Hare International?
No.
Which airlines fly most frequently between Portland and Chicago O'Hare International?
United (11 times daily), Lufthansa (6 times daily), SAS (5 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Portland to Chicago O'Hare International?
For Portland to Chicago O'Hare International, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago O'Hare International back to Portland, the best deals are generally found on Wednesday, with Monday being the most expensive.

Book cheap flights from Portland to Chicago O'Hare International (round-trip)

Airports
Origin
Portland
$160
only
$160
Destination
Chicago
$160
only
$160
Wed, Dec 6
PDX
ORD
17h 20m
Wed, Dec 13
ORD
PDX
17h 00m
Trip: 8 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 14 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PDX
ORD
Good 6.0

Drinking water serving was insufficient

AUS
IAD
Mediocre 2.0

2.5 hours delay is what I didn’t like

PDX
ORD
Okay 4.3

I like that they got me from one place to another.

They have new pre-reclined seats that basically hit curve in the middle. These are either made for a specific height or weren't tested. They make it so you have to sit hunched back the whole flight (I'm 5 10). If you have good posture, this airline is not for you.

PDX
ORD
Good 7.0

Seats were extremely uncomfortable

PDX
ORD
Good 6.0

The seats do not recline at all

Tue, May 1
PDX
ORD
6h 41m
Tue, May 8
ORD
PDX
10h 19m
Trip: 8 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

Tue, Dec 12
PDX
ORD
28h 22m
Wed, Dec 13
ORD
PDX
17h 00m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 15
PDX
ORD
3h 59m
Sat, Feb 17
ORD
PDX
4h 34m
Trip: 3 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 24 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PDX
ORD
Excellent 10.0

Nice clean plane prompt w drinks and food great attendants

Nothing. All was excellent

PDX
ORD
Mediocre 2.0

Due to mechanical issues our 8am flight kept getting delayed in 30 minute increments until around 9:45 when the front desk attendants told us the necessary part had to be driven from Seattle and wouldn't be available until noon, and that their was no certainty the part would work, and that we should make other arrangements. So we did, but their earliest we could get us into Chicago was 9:30pm (original arrival was 2pm). We booked the arrangements only to find out that our original flight took off at 10:55 and American didn't even attempt to contact us. The cherry on top was that our flight (which was indirect through SFO) got delayed and we're now going to miss our connection in SFO. So currently looking at 10:30pm arrival in Chicago.

PDX
ORD
Excellent 8.3

Because I could not really check in online early and I even called in to see why I had a very poor seat in the middle and service Of drinks with poor

PDX
ORD
Excellent 10.0

The in flight entertainment was perfect, new, and relevant. I also had an empty seat between myself and another passenger so my legs weren't as cramped.

PDX
ORD
Excellent 8.0

Pretty comfortable

Tue, Jan 9
PDX
ORD
10h 25m
Tue, Jan 16
ORD
PDX
19h 00m
Trip: 8 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 14 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PDX
ORD
Good 7.0

Seats were extremely uncomfortable

PDX
ORD
Good 6.0

Drinking water serving was insufficient

PDX
ORD
Mediocre 2.0

Nothing

The Customer service was horrible. The planes are very uncomfortable, ridiculous baggage fees. I Will never fly with them again.

PDX
ORD
Excellent 10.0

Everything was good

PDX
ORD
Okay 4.3

I like that they got me from one place to another.

They have new pre-reclined seats that basically hit curve in the middle. These are either made for a specific height or weren't tested. They make it so you have to sit hunched back the whole flight (I'm 5 10). If you have good posture, this airline is not for you.

Wed, Dec 6
PDX
ORD
17h 20m
Sat, Dec 9
ORD
PDX
9h 08m
Trip: 4 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 14 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PDX
ORD
Good 6.0

The seats do not recline at all

PDX
ORD
Excellent 10.0

The services on the flight

PDX
ORD
Good 6.0

Drinking water serving was insufficient

MKE
LAS
Okay 5.6

The crew was most friendly and accommodating. Pilots very informative made a could be turbulent flight very smooth.

Seats are very uncomfortable had a bar straight across bottom of my back. Lack of food and beverages. The plane should always be stocked.

PDX
ORD
Mediocre 2.0

Nothing. Frontier is simply dismal. Don't make the mistake of ever flying with them.

I had flown with Frontier previously, and so I didn't have initial qualms about booking a flight with them again. What I discovered is that in the past few years, Frontier was sold and the new owner has turned it into the worst airline on earth (literally ranked). Frontier's new game is to deceptively price their flights low so they are selected by people who book through 3rd party websites (we booked through Kayak). Around 35% of all flights are booked through 3rd party sites as of 2016. Then, once the flights are booked and are non-refundable, Frontier tells you during the check in process that you will have to pay through the nose for things that are free of charge on nearly every other airline in the world. For instance, we were told that unless we paid at least $16 per seat, my wife and I would be assigned random seats and would be unable to sit together. We were also told that it would cost us $40 for each CARRY-ON item we wanted to take on board with us. Yes, that is for carry-on items, not checked baggage, which they also charge you for. And the $40 mark is actually the internet discount, if you wait to check in at the airport, the price actually goes up to $60 per carry-on item. As would be expected, people don't like being deliberately deceived and fleeced like this, and they call customer service to complain. When I did this, the agent that I spoke to figured out quickly that I had a problem that would be moderately difficult to solve and simply hung up on me a minute or two into our conversation. This wasn't a fluke either, because when I called back, another agent did the same thing. I tried contacting them via twitter and got something similar. The agents simply stop responding to you when the realize the problem they might need to solve is more than moderately difficult. I would imagine that with the amount of complaints Frontier gets (highest in the industry by a wide margin), their reps are simply overworked and without hope. In fact, the only reason Frontier eventually responded to me was when I began reaching out to other disgruntled Frontier customers and suggesting that they could file complaints with the FAA. After 15 minutes of that, a somewhat senior customer service rep called me from Frontier's home office in Colorado and tried to explain to me why it was my fault for not reading the fine print and not assuming that an airline would deliberately try to deceive and then extort travelers. Ultimately, Frontier decided that they would refund our non-refundable tickets and we had a very pleasant experience flying on United. Even last minute, the tickets were only about $25 more apiece and we also were not charged $112 for the unheard of luxuries of sitting together and taking our carry-ons with us. So ultimately a huge savings. In my opinion, Kayak should remove Frontier and similar airlines (there are two-Spirit and Allegiant) from their search results as they are deliberately preying upon customers.

Thu, May 3
PDX
ORD
6h 41m
Mon, May 14
ORD
PDX
4h 17m
Trip: 12 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

Fri, Apr 20
PDX
ORD
4h 01m
Sun, Apr 22
ORD
PDX
4h 17m
Trip: 3 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

Tue, Mar 13
PDX
ORD
6h 16m
Fri, Mar 16
ORD
PDX
4h 25m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 13
PDX
ORD
6h 16m
Tue, Mar 20
ORD
PDX
7h 57m
Trip: 8 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

Fri, Feb 16
PDX
ORD
17h 53m
Mon, Feb 19
ORD
PDX
15h 45m
Trip: 4 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 14 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PDX
ORD
Excellent 10.0

Everything was good

PDX
ORD
Excellent 10.0

The services on the flight

PDX
ORD
Excellent 9.0

Great Service, On time.

Seats are pretty thin cushioned

PDX
ORD
Okay 4.3

I like that they got me from one place to another.

They have new pre-reclined seats that basically hit curve in the middle. These are either made for a specific height or weren't tested. They make it so you have to sit hunched back the whole flight (I'm 5 10). If you have good posture, this airline is not for you.

AUS
IAD
Mediocre 2.0

2.5 hours delay is what I didn’t like

Fri, Nov 24
PDX
ORD
7h 46m
Sun, Nov 26
ORD
PDX
6h 40m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Mon, Nov 27
PDX
ORD
24h 37m
Wed, Nov 29
ORD
PDX
9h 08m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 3
PDX
ORD
12h 46m
Sun, Jan 7
ORD
PDX
7h 36m
Trip: 5 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

Fri, Nov 24
PDX
ORD
5h 45m
Sun, Nov 26
ORD
PDX
24h 47m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Dec 22
PDX
ORD
6h 07m
Mon, Jan 1
ORD
PDX
7h 36m
Trip: 11 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.