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Find Cheap Flights from Portland to Chicago (PWM - CHI)

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Portland to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Portland
Flight Price $223
Distance 886 miles
Airlines American Airlines, JetBlue, Frontier, Delta, United

Good to Know

Average Price:
$326
(avg. price over the last 2 weeks)
Good Deal:
$279
or less (round trip)

When to Book Flights from Portland to Chicago

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $279 or less.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 29% 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 Flights

How long does a flight from Portland to Chicago take?
An average nonstop flight takes 3h 53m, covering a distance of 886 miles.
How many flights are there between Portland and Chicago?
There are 75 (nonstop) flights between Portland and Chicago per week, averaging 10 per day.
Which airlines provide the cheapest flights from Portland to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($223), JetBlue ($223) and Frontier ($242).
Do I need a passport to fly between Portland and Chicago?
No.
Which airlines fly most frequently between Portland and Chicago?
United (8 times daily), American Airlines (2 times daily), Southwest (0 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Portland to Chicago?
For Portland to Chicago, Thursday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Portland, the best deals are generally found on Thursday, with Wednesday being the most expensive.

Book cheap flights from Portland to Chicago (round-trip)

Airports
Origin
Portland
$223
only
$223
Destination
Chicago
$223
only
$223
$288
only
$288
Thu, Oct 25
PWM
Portland
ORD
Chicago O'Hare International
5h 08m
Wed, Oct 31
ORD
Chicago O'Hare International
PWM
Portland
6h 36m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 33,700 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.8
Food
6.7
BUD
PHL
Mediocre 3.0

Let's take a minute to thank American Airlines for assigning a 34 year old US Air plane without power outlets, entertainment options or even working personal lights for a trans-Atlantic flight. On the positive side, the seats were also very uncomfortable and had ashtrays!

PHL
BUD
Mediocre 3.6

The food was pretty good.

They had no accommodations for our baby, and didn’t let us board first. It was an old plane with basic entertainment, TVs above the middle row and not all do them worked. It was particularly freezing on board. Some of the crew was nice but overall not very friendly or welcoming.

ISP
PHL
Mediocre 2.0

Flight cancelled and had to travel 60 miles at my expense to a different airport to get another flight same day

MIA
MEX
Excellent 8.6

One of the stewardess felt like she was at her house with unwanted visitors, I guess. Very senile and careless attitude

BUD
PHL
Okay 5.0

We left on time and we arrived before schedule. They did let us board first with the baby.

The crew was not friendly and they didn’t come when we called for them. They did not have any accommodations for our baby. It was an old plane with very basic entertainment.

Wed, Nov 28
PWM
Portland
ORD
Chicago O'Hare International
5h 06m
Sun, Dec 2
ORD
Chicago O'Hare International
PWM
Portland
7h 15m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 13,247 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
PAP
JFK
Excellent 10.0

Crew staff is excellent

I enjoyed flying with jetblue

LAX
JFK
Excellent 10.0

Jetblue can't be beat! They are simply the best.

SFO
BOS
Excellent 8.0

Easy and comfortable. No issues. Got there without a problem.

BOS
BUF
Excellent 10.0

Boarded, departed and landed on time.

MBJ
JFK
Excellent 10.0

Departed on time arrived early Good legroom and ambiance

Fri, Dec 7
PWM
Portland
ORD
Chicago O'Hare International
7h 54m
Mon, Dec 10
ORD
Chicago O'Hare International
PWM
Portland
4h 39m
Trip: 4 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 35,383 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
DEN
Excellent 10.0

Customer service from check in and in flight was awesome.

LAS
CLE
Good 6.0

Smooth boarding, price was reasonable.

Seats stiff, no food, no entertainment

TTN
TPA
Mediocre 3.0

Boarding in a heavy rain. The flight was delayed hours. All passengers were extremely wet and the air conditioning was so high you could not even see through the fog in the cabin. I couldn’t see my seat number. We sat delayed on the plane with wet clothes for at least 90 min.

MCO
ONT
Okay 4.0

Clean smooth flight and nice crew

Rude woman at check in counter

MSY
DEN
Mediocre 2.0

Flight attendants were friendly

Delayed, broke down on runway, waiting for hours to take off. The bath rooms where dirty. Once we landed ,we had to wait a long time before we get off the plane.

Sat, Oct 27
PWM
Portland
MDW
Chicago Midway
7h 04m
Mon, Oct 29
MDW
Chicago Midway
PWM
Portland
5h 09m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

SFO
JFK
Good 7.0

Food was unexpectedly good.

The flight was delayed for 40 minutes. We could hardly catch connecting flight

BWI
JFK
Excellent 10.0

Excellent

ATL
MAD
Good 6.6

Crew was kind and responsive.

Older plane so seats were very crammed. My screen was not calibrated correctly so I couldn’t rewind or pause movies. No charging option for phone. WiFi was spotty.

Thu, Nov 1
PWM
Portland
ORD
Chicago O'Hare International
4h 36m
Sun, Nov 4
ORD
Chicago O'Hare International
PWM
Portland
7h 15m
Trip: 4 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 32 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
PWM
ORD
Good 7.0

Kayak did not provide me with confirming email for flight in either direction and I missed my first flight to LA from Portland This is the second time I was not contacted via email from Kayak on flight reservations

PWM
ORD
Mediocre 2.0

Flight did not happen

PWM
ORD
Okay 5.3

Seating next to the bathroom is gross

PWM
ORD
Excellent 8.3

Couldn't really figure out your Wi-Fi system so I just read a book

It's not really easy to set up your Wi-Fi system through the United app

PWM
ORD
Mediocre 3.6

Nothing

Payed to upgrade seat was not comfortable and person next to me kept moving onto my side. Flight was 2 hours late so I missed my connection and had a terrible time to find a flight home. United staff was not helpful and kept telling me to go somewhere else for help. No food was served only tiny packet of way too spicy pretzels. Sat on the runway for an hour. Flight crew said 15 min and it was much longer. Crew seemed to be really confused.

Fri, Oct 26
PWM
Portland
ORD
Chicago O'Hare International
6h 05m
Mon, Oct 29
ORD
Chicago O'Hare International
PWM
Portland
2h 14m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 33,700 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.8
Food
6.7
LIM
SAL
Good 7.0

Latam would not transfer 1 medium baggage from LATAM to Avianca at Lima

FAY
CLT
Excellent 10.0

Smooth flight

Tight fit for 6'3 male

MIA
MEX
Excellent 8.6

One of the stewardess felt like she was at her house with unwanted visitors, I guess. Very senile and careless attitude

BUD
PHL
Mediocre 3.0

Let's take a minute to thank American Airlines for assigning a 34 year old US Air plane without power outlets, entertainment options or even working personal lights for a trans-Atlantic flight. On the positive side, the seats were also very uncomfortable and had ashtrays!

LAS
MIA
Okay 5.6

On time flight

Crampy space.

Wed, Dec 5
PWM
Portland
MDW
Chicago Midway
7h 17m
Sat, Dec 8
MDW
Chicago Midway
PWM
Portland
4h 23m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

RDU
SLC
Excellent 10.0

The flight crew was so nice! Roomy seats and plenty of snacks!

BWI
JFK
Excellent 10.0

Excellent

ATL
MAD
Good 6.6

Crew was kind and responsive.

Older plane so seats were very crammed. My screen was not calibrated correctly so I couldn’t rewind or pause movies. No charging option for phone. WiFi was spotty.

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

Thu, Nov 29
PWM
Portland
MDW
Chicago Midway
7h 17m
Sun, Dec 2
MDW
Chicago Midway
PWM
Portland
6h 54m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

ATL
MAD
Good 6.6

Crew was kind and responsive.

Older plane so seats were very crammed. My screen was not calibrated correctly so I couldn’t rewind or pause movies. No charging option for phone. WiFi was spotty.

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

JFK
PRG
Good 7.6

Complimentary beverages.

Chicken and pasta for dinner

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Mon, Dec 24
PWM
Portland
ORD
Chicago O'Hare International
5h 18m
Mon, Dec 31
ORD
Chicago O'Hare International
PWM
Portland
6h 50m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

JFK
PRG
Good 7.6

Complimentary beverages.

Chicken and pasta for dinner

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

BWI
JFK
Excellent 10.0

Excellent

Fri, Mar 15
PWM
Portland
MDW
Chicago Midway
4h 12m
Mon, Mar 18
MDW
Chicago Midway
PWM
Portland
6h 56m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

JFK
PRG
Good 7.6

Complimentary beverages.

Chicken and pasta for dinner

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

Fri, Nov 2
PWM
Portland
MDW
Chicago Midway
3h 53m
Sun, Nov 4
MDW
Chicago Midway
PWM
Portland
4h 07m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

RDU
SLC
Excellent 10.0

The flight crew was so nice! Roomy seats and plenty of snacks!

JFK
PRG
Good 7.6

Complimentary beverages.

Chicken and pasta for dinner

Fri, Oct 5
PWM
Portland
MDW
Chicago Midway
4h 44m
Mon, Oct 8
MDW
Chicago Midway
PWM
Portland
4h 23m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,295 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

BWI
JFK
Excellent 10.0

Excellent

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

JFK
PRG
Good 7.6

Complimentary beverages.

Chicken and pasta for dinner

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

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