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

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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
December
Most popular time to fly
3%
expected price increase
Average Price:
$446
(avg. price over the last 2 weeks)
Good Deal:
$311
or less (round trip)

When to Book Flights from Chicago 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 to Portland was found 90 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 101% 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 Chicago to Portland Flights

How long does a flight from Chicago to Portland take?
An average nonstop flight takes 4h 16m, covering a distance of 886 miles.
How many flights are there between Chicago and Portland?
There are 14 (nonstop) flights between Chicago and Portland per week, averaging 2 per day.
Which airlines provide the cheapest flights from Chicago to Portland?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($143), JetBlue ($213) and Multiple Airlines ($262).
Do I need a passport to fly between Chicago and Portland?
No.
Which airlines fly most frequently between Chicago and Portland?
United (2 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to Portland?
For Chicago to Portland, Saturday is the cheapest day to fly on average and Friday is the most expensive. Flying from Portland back to Chicago, the best deals are generally found on Saturday, with Thursday being the most expensive.

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

Airports
Origin
Chicago
$143
only
$143
Destination
Portland
$143
only
$143
Sat, Feb 3
ORD
PWM
5h 52m
Wed, Feb 7
PWM
ORD
6h 18m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
NAS
MIA
Mediocre 2.0

We had to wait almost two hrs on the plane before take off.

LGA
CLT
Excellent 10.0

We had two medical emergency on board so the flight attendant took care of them really well

They check in my hand carry my whole point of carrying is not to be bother with claing my luggage

DFW
GEG
Excellent 8.0

Food could have been better. Plane was 1/2 full. WiFi was not giving all the movies. Only 6 or 7 to choose from.

MAD
PHL
Mediocre 2.0

Missed it!

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

Sat, Jun 2
ORD
PWM
5h 16m
Tue, Jun 5
PWM
ORD
8h 10m
Trip: 4 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7714 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

MCO
SLC
Excellent 9.3

Crew was polite at the gate and on board. Flight went smoothly, temp was comfortable. Love the individual screens for all.

My sons tv screen wasn't working. I pushed the attendant button to see if they could help, nobody ever came. I left in on for quite awhile too. Wi Fi was hard to log into.

SEA
JFK
Good 7.3

crew very unfriemdly

FLL
SAN
Excellent 10.0

I love JetBlue. I love everything about the airline. I love the free wifi and snacks. The seats are comfortable and I actually have room to lay my head down in economy. I love jet blue so much I am always willing to pay extra to fly with the airline. The customer service is superb and I have never had anything but an extremely possitive experience with this airline.

Nothing to complain about at all. Overall a great airline

FLL
LGA
Mediocre 3.6

Ive been traveling with jetblue for years, but lately everytime their flights are always delay

Thu, Jun 21
ORD
PWM
4h 16m
Tue, Jun 26
PWM
ORD
6h 13m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 6
ORD
PWM
5h 22m
Wed, Feb 7
PWM
ORD
6h 18m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MAD
PHL
Mediocre 2.0

Missed it!

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

DFW
GEG
Excellent 8.0

Food could have been better. Plane was 1/2 full. WiFi was not giving all the movies. Only 6 or 7 to choose from.

SLC
CLT
Okay 4.0

Flight attendants

The flight got delayed from salt lake and we had to spend a day in Charlotte before another flight came

NAS
MIA
Mediocre 2.0

We had to wait almost two hrs on the plane before take off.

Fri, Apr 13
ORD
PWM
5h 52m
Tue, Apr 17
PWM
ORD
7h 52m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HOU
Excellent 10.0

Nice flight and good staff and service

CVG
SFO
Okay 5.6

Boarding was fine. And service was good.

TV controls didn’t work. So I couldn’t watch anything for the 4+ hour flight.

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

Sat, Feb 3
ORD
PWM
7h 08m
Tue, Feb 6
PWM
ORD
5h 15m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ORD
PHL
Mediocre 2.0

Nothing - the flight from Chicago to Philadelphia was delayed by about 2 hours. Luckily, was able to get the flight switched to a Chicago - London direct flight.

The connecting flight from Philadelphia to Manchester would've been missed. So, American Airlines booked the same flight for 24 hours later. Luckily, they offered a different flight. Due to the flight changes, the prepaid ground transportation from Manchester to Leeds wasn't used. Transportation from London to Leeds had to be purchased at a much greater additional expense.

SNA
DFW
Mediocre 3.6

We were unfortunately stuck on the tarmac for 45 minutes. I ran to my connecting gate but they had already closed it. There wasn’t a service rep at the gate. I walked to another gate and there was a very helpful rep who rebooked me to a nearby city. It overall was disappointing and caused me to get home about 3 1/2 hours later.

MAD
PHL
Mediocre 2.0

Missed it!

SFO
LAX
Excellent 10.0

great flight

MAD
PHL
Good 7.0

Flight was not full.

Luggage was very late and arrived at the wrong carousel.

Sat, Feb 3
ORD
PWM
7h 08m
Fri, Feb 9
PWM
ORD
6h 03m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MIA
DCA
Excellent 10.0

New plane, 737-Max. More fuel efficient, quieter, more in-cabin luggage storage.

Seats don’t decline as much.

SLC
CLT
Okay 4.0

Flight attendants

The flight got delayed from salt lake and we had to spend a day in Charlotte before another flight came

ORD
PHL
Mediocre 2.0

Nothing - the flight from Chicago to Philadelphia was delayed by about 2 hours. Luckily, was able to get the flight switched to a Chicago - London direct flight.

The connecting flight from Philadelphia to Manchester would've been missed. So, American Airlines booked the same flight for 24 hours later. Luckily, they offered a different flight. Due to the flight changes, the prepaid ground transportation from Manchester to Leeds wasn't used. Transportation from London to Leeds had to be purchased at a much greater additional expense.

NAS
MIA
Mediocre 2.0

We had to wait almost two hrs on the plane before take off.

SNA
DFW
Mediocre 3.6

We were unfortunately stuck on the tarmac for 45 minutes. I ran to my connecting gate but they had already closed it. There wasn’t a service rep at the gate. I walked to another gate and there was a very helpful rep who rebooked me to a nearby city. It overall was disappointing and caused me to get home about 3 1/2 hours later.

Sun, Feb 4
ORD
PWM
5h 22m
Wed, Feb 7
PWM
ORD
7h 47m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SNA
DFW
Mediocre 3.6

We were unfortunately stuck on the tarmac for 45 minutes. I ran to my connecting gate but they had already closed it. There wasn’t a service rep at the gate. I walked to another gate and there was a very helpful rep who rebooked me to a nearby city. It overall was disappointing and caused me to get home about 3 1/2 hours later.

ORD
PHL
Mediocre 2.0

Nothing - the flight from Chicago to Philadelphia was delayed by about 2 hours. Luckily, was able to get the flight switched to a Chicago - London direct flight.

The connecting flight from Philadelphia to Manchester would've been missed. So, American Airlines booked the same flight for 24 hours later. Luckily, they offered a different flight. Due to the flight changes, the prepaid ground transportation from Manchester to Leeds wasn't used. Transportation from London to Leeds had to be purchased at a much greater additional expense.

LGA
CLT
Excellent 10.0

We had two medical emergency on board so the flight attendant took care of them really well

They check in my hand carry my whole point of carrying is not to be bother with claing my luggage

MAD
PHL
Mediocre 2.0

Missed it!

DFW
BMI
Mediocre 3.6

I didn’t make this flight.

Tue, Feb 6
ORD
PWM
5h 52m
Fri, Feb 9
PWM
ORD
7h 47m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LGA
CLT
Excellent 10.0

We had two medical emergency on board so the flight attendant took care of them really well

They check in my hand carry my whole point of carrying is not to be bother with claing my luggage

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

SFO
LAX
Excellent 10.0

great flight

MIA
DCA
Excellent 10.0

New plane, 737-Max. More fuel efficient, quieter, more in-cabin luggage storage.

Seats don’t decline as much.

MAD
PHL
Mediocre 2.0

Missed it!

Sun, Jun 24
ORD
PWM
8h 46m
Tue, Jun 26
PWM
ORD
6h 13m
Trip: 3 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7714 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
MBJ
JFK
Excellent 8.6

Pilot letting us know as we experience turbulence that arose from severe weather conditions, which we would pass through.

Pilot predicting before take-off that there would likely be no turbulence; then there was turbulence due to weather conditions.

BOS
PHL
Good 6.0

Comfy, cheap upgrades, ammenable crew

Late! I know there's no control over the weather but I don't have to be happy about it.

FLL
SAN
Excellent 10.0

I love JetBlue. I love everything about the airline. I love the free wifi and snacks. The seats are comfortable and I actually have room to lay my head down in economy. I love jet blue so much I am always willing to pay extra to fly with the airline. The customer service is superb and I have never had anything but an extremely possitive experience with this airline.

Nothing to complain about at all. Overall a great airline

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

DCA
MCO
Mediocre 2.3

Late plane. No explanation. Orlando arrrival

Sun, May 27
ORD
PWM
12h 39m
Wed, May 30
PWM
ORD
5h 54m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 28
ORD
PWM
5h 52m
Mon, Apr 30
PWM
ORD
5h 53m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

PDX
JFK
Excellent 8.3

Food

Leg room

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

Sun, Jul 29
ORD
PWM
8h 46m
Fri, Aug 31
PWM
ORD
6h 56m
Trip: 34 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7714 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
SEA
JFK
Good 7.3

crew very unfriemdly

DCA
MCO
Mediocre 2.3

Late plane. No explanation. Orlando arrrival

FLL
BOS
Mediocre 2.0

Nothing

Overhead reading lights didn’t work, my partners tv didn’t work, the movie I had was only in Spanish and the overhead bins were too small and had to gate check my bag Sloppy plane maintenance by JetBlue Not worth the extra money to sit in extra leg room seats over$120 for two of us

BOS
PHL
Good 6.0

Comfy, cheap upgrades, ammenable crew

Late! I know there's no control over the weather but I don't have to be happy about it.

MCO
SLC
Excellent 9.3

Crew was polite at the gate and on board. Flight went smoothly, temp was comfortable. Love the individual screens for all.

My sons tv screen wasn't working. I pushed the attendant button to see if they could help, nobody ever came. I left in on for quite awhile too. Wi Fi was hard to log into.

Sun, Feb 4
ORD
PWM
5h 22m
Fri, Feb 9
PWM
ORD
6h 03m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MAD
PHL
Good 7.0

Flight was not full.

Luggage was very late and arrived at the wrong carousel.

LGA
CLT
Excellent 10.0

We had two medical emergency on board so the flight attendant took care of them really well

They check in my hand carry my whole point of carrying is not to be bother with claing my luggage

DFW
GEG
Excellent 8.0

Food could have been better. Plane was 1/2 full. WiFi was not giving all the movies. Only 6 or 7 to choose from.

NAS
MIA
Mediocre 2.0

We had to wait almost two hrs on the plane before take off.

SFO
LAX
Excellent 10.0

great flight

Thu, Feb 8
ORD
PWM
6h 29m
Fri, Feb 9
PWM
ORD
6h 03m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 9
ORD
PWM
5h 34m
Sat, Jun 16
PWM
ORD
7h 49m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PDX
JFK
Excellent 8.3

Food

Leg room

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

Mon, Jul 30
ORD
PWM
8h 46m
Fri, Aug 31
PWM
ORD
6h 56m
Trip: 33 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7714 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
LGA
Mediocre 3.6

Ive been traveling with jetblue for years, but lately everytime their flights are always delay

DFW
BOS
Good 7.0

Nice crew, comfortable seats.

Delayed flight, broken TV and terrible boarding process. Frozen toilet chemicals.

SEA
JFK
Good 7.3

crew very unfriemdly

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

MBJ
JFK
Excellent 8.6

Pilot letting us know as we experience turbulence that arose from severe weather conditions, which we would pass through.

Pilot predicting before take-off that there would likely be no turbulence; then there was turbulence due to weather conditions.

Mon, Feb 5
ORD
PWM
7h 51m
Fri, Feb 9
PWM
ORD
6h 03m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27334 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LGA
CLT
Excellent 10.0

We had two medical emergency on board so the flight attendant took care of them really well

They check in my hand carry my whole point of carrying is not to be bother with claing my luggage

SFO
LAX
Excellent 10.0

great flight

SNA
DFW
Mediocre 3.6

We were unfortunately stuck on the tarmac for 45 minutes. I ran to my connecting gate but they had already closed it. There wasn’t a service rep at the gate. I walked to another gate and there was a very helpful rep who rebooked me to a nearby city. It overall was disappointing and caused me to get home about 3 1/2 hours later.

DFW
GEG
Excellent 8.0

Food could have been better. Plane was 1/2 full. WiFi was not giving all the movies. Only 6 or 7 to choose from.

SLC
CLT
Okay 4.0

Flight attendants

The flight got delayed from salt lake and we had to spend a day in Charlotte before another flight came

Fri, Mar 2
ORD
PWM
7h 08m
Mon, Mar 5
PWM
ORD
6h 04m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jul 28
ORD
PWM
5h 34m
Thu, Aug 2
PWM
ORD
6h 15m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

Show more results

Chicago to Portland Flight Information

Flights Arrive in Portland
Flights Depart from Chicago
Flight Price $143
Distance 886 miles
Airlines American Airlines, JetBlue, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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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.