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

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Good to Know

Low Season:
January
Best time to beat the crowds
3%
expected price decrease
High Season:
July
Most popular time to fly
11%
expected price increase
Average Price:
$452
(avg. price over the last 2 weeks)
Good Deal:
$311
or less (round trip)

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

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 $311 or less.
The cheapest flight from Chicago O'Hare International to Portland was found 31 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 June, July and August. The cheapest month to fly is January.
Morning departure is around 2% 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 Chicago O'Hare International to Portland Flights

How long does a flight from Chicago O'Hare International to Portland take?
An average nonstop flight takes 3h 57m, covering a distance of 898 miles.
How many flights are there between Chicago O'Hare International and Portland?
There are 34 (nonstop) flights between Chicago O'Hare International and Portland per week, averaging 5 per day.
Which airlines provide the cheapest flights from Chicago O'Hare International to Portland?
In the past 3 days, the cheapest round-trip tickets were found on JetBlue ($188), Multiple Airlines ($237) and Delta ($286).
Do I need a passport to fly between Chicago O'Hare International and Portland?
No.
Which airlines fly most frequently between Chicago O'Hare International and Portland?
United (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago O'Hare International to Portland?
For Chicago O'Hare International to Portland, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Portland back to Chicago O'Hare International, the best deals are generally found on Monday, with Friday being the most expensive.

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

Airports
Origin
Chicago
$188
only
$188
Destination
Portland
$188
only
$188
Mon, May 14
ORD
PWM
4h 19m
Tue, May 22
PWM
ORD
5h 54m
Trip: 9 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
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.

JFK
SYR
Good 7.0

TV didn't work

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.

FLL
LAS
Good 6.3

The flight was delayed by 2 hours

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

Fri, Jun 1
ORD
PWM
4h 47m
Wed, Jun 6
PWM
ORD
5h 54m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Apr 13
ORD
PWM
5h 47m
Mon, Apr 16
PWM
ORD
5h 44m
Trip: 4 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
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

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.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Sun, Dec 31
ORD
PWM
5h 51m
Fri, Jan 5
PWM
ORD
6h 04m
Trip: 6 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
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.

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.

PHL
ATL
Okay 5.3

On time

Rude flight attendant

ORD
LAX
Excellent 9.5

Easy, smooth.

CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

Tue, May 22
ORD
PWM
8h 27m
Wed, May 30
PWM
ORD
5h 54m
Trip: 9 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
FLL
LAS
Good 6.3

The flight was delayed by 2 hours

BOS
PBI
Excellent 8.3

my attendant

MCO
PVD
Excellent 10.0

Great flight great experience

Long lines at TSA checkpoint.

FLL
KIN
Okay 4.0

The flight attendants were pleasant and courteous

The boarding was delayed and the boarding area was crowded, Boarding was delayed due to high number of wheelchair passengers. I was seated in an Even More Space seat, yet was placed beside a woman who was obviously suffering from some degenerative condition, and was slumped over towards my seat. The result was that I was uncomfortable the whole way back to Kingston.

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.

Wed, Jun 6
ORD
PWM
8h 27m
Tue, Jun 12
PWM
ORD
7h 40m
Trip: 7 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
FLL
LAS
Good 6.3

The flight was delayed by 2 hours

BOS
PBI
Excellent 8.3

my attendant

SEA
JFK
Excellent 8.0

no power outlets

BOS
DCA
Mediocre 2.0

There was a huge glitch in your ticketing, resulting in me confirming the same ticket 3 times. After calling Jetblue for customer service per your advice, they first suggested to give Jetblue credits for extra tickets. When I insisted that the issue was solely caused by kayak-jetblue ticketing connection issues, they supervisor approved to cancel 2 credit card payments... BUT I have to wait for 2 weeks to see the cancellation on my credit card. Unfair and ridiculous, if you as me.

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.

Thu, Jan 25
ORD
PWM
5h 01m
Tue, Jan 30
PWM
ORD
6h 55m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 9
ORD
PWM
4h 09m
Mon, Mar 12
PWM
ORD
7h 24m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 14
ORD
PWM
5h 52m
Tue, Apr 17
PWM
ORD
4h 44m
Trip: 4 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
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Fri, Feb 2
ORD
PWM
4h 34m
Sun, Feb 4
PWM
ORD
5h 35m
Trip: 3 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
DCA
Excellent 10.0

Left on time and arrived early both ways.

BOS
PBI
Excellent 8.3

my attendant

SEA
JFK
Excellent 8.0

no power outlets

FLL
KIN
Okay 4.0

The flight attendants were pleasant and courteous

The boarding was delayed and the boarding area was crowded, Boarding was delayed due to high number of wheelchair passengers. I was seated in an Even More Space seat, yet was placed beside a woman who was obviously suffering from some degenerative condition, and was slumped over towards my seat. The result was that I was uncomfortable the whole way back to Kingston.

JFK
ABQ
Good 7.3

I know it's hard to make a 14+ hour flight in economy enjoyable, but more varied food selections and better/more current movies to choose from would have helped.

Tue, Jan 9
ORD
PWM
4h 34m
Wed, Jan 10
PWM
ORD
5h 37m
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
BOS
PBI
Excellent 8.3

my attendant

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

MCO
PVD
Excellent 10.0

Great flight great experience

Long lines at TSA checkpoint.

FLL
KIN
Okay 4.0

The flight attendants were pleasant and courteous

The boarding was delayed and the boarding area was crowded, Boarding was delayed due to high number of wheelchair passengers. I was seated in an Even More Space seat, yet was placed beside a woman who was obviously suffering from some degenerative condition, and was slumped over towards my seat. The result was that I was uncomfortable the whole way back to Kingston.

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.

Thu, Dec 21
ORD
PWM
5h 20m
Sat, Dec 30
PWM
ORD
7h 23m
Trip: 10 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
CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

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.

YUL
MIA
Excellent 10.0

First time flyer with American airlines and the service was impeccable

Nothing to dislike

JFK
CDG
Mediocre 2.0

Nothing. From the plane to the awful delay and poor service.

Lack of communication. Old plane, no comfort and 6 HOURS DELAYED. Truly disappointed by the airline

ORD
LAX
Excellent 9.5

Easy, smooth.

Fri, Mar 2
ORD
PWM
3h 57m
Wed, Mar 7
PWM
ORD
5h 04m
Trip: 6 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
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

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.

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