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

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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
August
Most popular time to fly
4%
expected price increase
Average Price:
$433
(avg. price over the last 2 weeks)
Good Deal:
$283
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 $282 or less.
The cheapest flight from Portland to Chicago O'Hare International was found 48 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
High season is considered to be July, August and September. The cheapest month to fly is January.
Morning departure is around 15% 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

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 5h 02m, covering a distance of 898 miles.
How many flights are there between Portland and Chicago O'Hare International?
There are 47 (nonstop) flights between Portland and Chicago O'Hare International per week, averaging 6 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 JetBlue ($213), Multiple Airlines ($248) and American Airlines ($259).
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 (6 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, Monday 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 Tuesday, with Friday being the most expensive.

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

Airports
Origin
Portland
$213
only
$213
Destination
Chicago
$213
only
$213
Mon, Jan 22
PWM
ORD
5h 37m
Tue, Jan 23
ORD
PWM
4h 34m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 7213 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
MCO
PVD
Excellent 10.0

Great flight great experience

Long lines at TSA checkpoint.

SFO
FLL
Good 7.0

Once again the system for my seat did not work. Fortunately, the middle seat was empty and I wa able to watch that screen.

Entertainment System did not work at my seat. WiFi signal was not strong enough for me to watch any videos on my device.

FLL
RDU
Excellent 8.3

The departure and arrival times were accurate. Actually we arrived about 15 minutes early.

There was only one individual checking people boarding. Two individuals at the boarding gate would have been even more efficient.

PHX
JFK
Good 7.6

The staff is friendlier than most airlines. More room than American.

Screaming child entire flight. Not sure there is a solution. But, for a redeye, trying to get sleep before a days work, not great.

BOS
PBI
Excellent 8.3

my attendant

Thu, Mar 8
PWM
ORD
7h 24m
Mon, Mar 12
ORD
PWM
12h 52m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 19
PWM
ORD
6h 18m
Thu, Jan 25
ORD
PWM
7h 08m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ORD
LAX
Excellent 9.5

Easy, smooth.

DFW
PBI
Okay 5.6

Free movies, and crew were helpful once we were in the air

Gate agent did not start forcing check in, which caused delay in boarding. Ground crew did not stock aircraft until 20 minutes after scheduled departure time. and DFW did the usual 20 minute taxi and then 15 minute hold prior to take off.

SFO
DFW
Excellent 10.0

On time. Comfortable seat. Courteous crew. Easy transfer.

JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

LAX
LHR
Excellent 9.2

Easy and efficient boarding for a busy flight. Efficient, attentive and intuitive cabin crew. Good in-flight entertainment and facilities.

The aircraft was extremely cold throughout the duration of the flight. Of all of the long haul airlines I've flown with, I find that American Airlines offers the least leg room.

Wed, Feb 28
PWM
ORD
5h 30m
Sat, Mar 3
ORD
PWM
5h 22m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SFO
DFW
Excellent 10.0

On time. Comfortable seat. Courteous crew. Easy transfer.

JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

YUL
MIA
Excellent 10.0

First time flyer with American airlines and the service was impeccable

Nothing to dislike

DFW
PBI
Okay 5.6

Free movies, and crew were helpful once we were in the air

Gate agent did not start forcing check in, which caused delay in boarding. Ground crew did not stock aircraft until 20 minutes after scheduled departure time. and DFW did the usual 20 minute taxi and then 15 minute hold prior to take off.

LAX
AKL
Okay 5.6

Smooth operation, on time

Seat pitch on the plane unbelievably cramped. When seats are so close that if you drop something on the floor you have to be a contortionist to get it, you know it's a problem NEVER fly the 787-900 economy.

Mon, Mar 5
PWM
ORD
5h 10m
Thu, Mar 8
ORD
PWM
7h 08m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DFW
PBI
Okay 5.6

Free movies, and crew were helpful once we were in the air

Gate agent did not start forcing check in, which caused delay in boarding. Ground crew did not stock aircraft until 20 minutes after scheduled departure time. and DFW did the usual 20 minute taxi and then 15 minute hold prior to take off.

JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

YUL
MIA
Excellent 10.0

First time flyer with American airlines and the service was impeccable

Nothing to dislike

LAX
LHR
Excellent 9.2

Easy and efficient boarding for a busy flight. Efficient, attentive and intuitive cabin crew. Good in-flight entertainment and facilities.

The aircraft was extremely cold throughout the duration of the flight. Of all of the long haul airlines I've flown with, I find that American Airlines offers the least leg room.

CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

Fri, Jan 26
PWM
ORD
5h 02m
Sun, Jan 28
ORD
PWM
3h 48m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Thu, Dec 28
PWM
ORD
5h 02m
Thu, Jan 4
ORD
PWM
5h 51m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DFW
PBI
Okay 5.6

Free movies, and crew were helpful once we were in the air

Gate agent did not start forcing check in, which caused delay in boarding. Ground crew did not stock aircraft until 20 minutes after scheduled departure time. and DFW did the usual 20 minute taxi and then 15 minute hold prior to take off.

CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

BNA
DFW
Good 7.3

Everything else

PHL
ATL
Okay 5.3

On time

Rude flight attendant

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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.