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

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Wed 2/21
Wed 2/28
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Good to Know

Low Season:
May
Best time to beat the crowds
2%
expected price decrease
High Season:
March
Most popular time to fly
10%
expected price increase
Average Price:
$724
(avg. price over the last 2 weeks)
Good Deal:
$556
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

The cheapest flight from Chicago to Portland was found 30 days before departure, on average.
Book at least 3 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 May.
Morning departure is around 5% 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 to Portland Flights

How long does a flight from Chicago to Portland take?
An average nonstop flight takes 4h 20m, covering a distance of 1750 miles.
How many flights are there between Chicago and Portland?
There are 262 (nonstop) flights between Chicago and Portland per week, averaging 36 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 Spirit Airlines ($157), Frontier ($193) and Multiple Airlines ($212).
Do I need a passport to fly between Chicago and Portland?
No.
Which airlines fly most frequently between Chicago and Portland?
United (7 times daily), Alaska Airlines (5 times daily), SAS (5 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, Thursday 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 Tuesday, with Saturday being the most expensive.

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

Airports
Origin
Chicago
$157
only
$157
$294
only
$294
Destination
Portland
$157
only
$157
Thu, Apr 12
ORD
PDX
4h 20m
Sun, Apr 15
PDX
ORD
3h 56m
Trip: 4 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Mediocre 2.0

Flight from Dallas to Chicago was delayed 2.5 hours, so they pulled me off the plane when it was finally time to board, telling me id miss my connecting flight. There needs to be a better way to handle that, the level of inconvenience set upon me was massive.

ORD
PDX
Mediocre 2.6

No sense of urgency

ORD
PDX
Mediocre 2.6

It was the same as the first leg of my flight. Not good

The same as the first flight. I will not fly Spirit Airlines ever again.

ORD
PDX
Okay 4.6

I like that I was seated in the window seat and that there was space for me to move around in my seat and be able to sleep

the delays in boarding, last minute gate changes, how you have to pay for a drink, no free food at all, which sucks if you are on a budget. I was supposed to be there at 11 but it turned to be 2 am.

ORD
PDX
Mediocre 2.0

nothing

Everything. I'm never flying Spirit again. My vacation was almost because they have no idea how to run an airline. Plus, their baggage fees are ridiculous. I'm telling everybody I know to never fly Spirit.

Wed, Feb 28
ORD
PDX
8h 46m
Thu, Mar 1
PDX
ORD
21h 05m
Trip: 2 days
6.3GoodShow reviews
Overall 6.3 Good
Based on 9 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
ORD
PDX
Okay 4.0

Middle seat was empty

The delay. No food. No apologies

ORD
PDX
Good 6.0

New Planes.

Flight was 55 minutes late to board.

PHL
SJU
Good 6.0

boarding and treatment by staff wad excellent

$3 for a cup of coffee is outrageous.... other airlines at least include beverages and a snack (peanuts etc).

PHX
MKE
Okay 4.0

Nothing

Everything

ORD
PDX
Mediocre 3.6

Extra fees for everything. Worst seats on any plane flown. Delayed with no explanation.

Wed, Mar 28
ORD
PDX
4h 29m
Tue, May 1
PDX
ORD
3h 56m
Trip: 35 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 13
MDW
PDX
9h 02m
Sat, Mar 17
PDX
MDW
7h 16m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
LAX
Excellent 10.0

The in flight entertainment was superb.

I have no complaints.

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

LAX
JFK
Excellent 10.0

I was able to pass the time with ease. A+++ in flight experiences. Great airline staff and awesome food.

No complaints whatsoever.

ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

Thu, Apr 12
ORD
PDX
4h 20m
Sun, Apr 15
PDX
ORD
3h 56m
Trip: 4 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Good 6.4

The flight took off on time, as expected. The crew was super positive and friendly. Boarding went smoothly and quickly.

Seats are small, as expected. Gates switched and it was only announced, never made public on the flight update website.

ORD
PDX
Okay 4.0

2 hours late leaving chicago

ORD
PDX
Mediocre 2.6

It was the same as the first leg of my flight. Not good

The same as the first flight. I will not fly Spirit Airlines ever again.

ORD
PDX
Mediocre 3.0

It took me from point A to point B.

Baggage fees are ridiculous. Never again with Spirit.

ORD
PDX
Mediocre 2.0

Cancelled my flight TO Chicago. Next flight they could get me on was four days later! Then, lost my luggage on way from Chicago back to Portland. Agent lied to us that an agent had gone down to baggage desk to help us...we were sitting AT the desk the entire time and no one showed up. Now no one is available to discuss location / status of my suitcase, and the ETA. No one answers the phone at the number given to me. Poor, poor customer service.

Thu, Mar 22
ORD
PDX
4h 29m
Fri, Mar 30
PDX
ORD
4h 04m
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 18768 reviews
Overall
8.3
Boarding
8.4
Comfort
8.2
Crew
8.5
Entertainment
8.1
Food
7.7
LAS
JFK
Excellent 10.0

Boarded on time, had great entertainment on board, comfortable seats, and we arrived early!

No complaints.

SAN
SFO
Mediocre 2.0

The flight was booked wrong. When I contacted Virgin America to get another flight; they sent me to another airport, and the agent booked the wrong date. I cancelled the flight and took two busses, and two trains to get home.

JFK
LAX
Okay 4.0

Staff attitude. They appeared to be bothered if you asked for help.

LAX
LAS
Excellent 10.0

Plane

SFO
LAX
Okay 5.2

My family and I were eating and waiting to board our plane at gate 54 on Virgin flight 1948 and my wife was talking to some other people also waiting to board the plane at gate 54 on Virgin flight 1948. They were saying that there weren't very many people at our gate to board the flight so they went to investigate what might be happening and found out the gate to board Virgin flight 1948 was not at gate 54 which was the gate number printed on our boarding pass but was at a different gate on the other side of San Francisco airport at gate 47. What aggravated me was that no one came over to tell us the gate number was changed. We could have very easily missed our flight. And no one at the Virgin check in seemed to care. I'm very dissatisfied with the customer service when it comes to making sure passengers know that there have been gate changes. We almost missed our flight.

Tue, May 1
ORD
PDX
4h 20m
Fri, May 4
PDX
ORD
3h 56m
Trip: 4 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Mediocre 2.0

Cancelled my flight TO Chicago. Next flight they could get me on was four days later! Then, lost my luggage on way from Chicago back to Portland. Agent lied to us that an agent had gone down to baggage desk to help us...we were sitting AT the desk the entire time and no one showed up. Now no one is available to discuss location / status of my suitcase, and the ETA. No one answers the phone at the number given to me. Poor, poor customer service.

ORD
PDX
Okay 5.3

Price

Uncomfortable

ORD
PDX
Mediocre 3.3

The crew was great even though the airline was having problems.

The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice.

ORD
PDX
Mediocre 2.6

No sense of urgency

ORD
PDX
Okay 5.5

The airplanes seemed new, and the flight back was on time.

Primarily the pricing is deceptive because things that included in the ticket price on most major airlines (e.g., 1 carry-on bag, a seat on the plane, soft drinks) must be paid for after buying the ticket. Fees just for a carry-on bag and selecting a seat on the plane added up to nearly $130 over the advertised ticket, and would have been more had I not checked in before leaving for the airport.

Fri, May 4
ORD
PDX
4h 20m
Sun, May 6
PDX
ORD
3h 56m
Trip: 3 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Okay 4.0

2 hours late leaving chicago

ORD
PDX
Mediocre 2.0

Flight from Dallas to Chicago was delayed 2.5 hours, so they pulled me off the plane when it was finally time to board, telling me id miss my connecting flight. There needs to be a better way to handle that, the level of inconvenience set upon me was massive.

ORD
PDX
Mediocre 2.0

Cancelled my flight TO Chicago. Next flight they could get me on was four days later! Then, lost my luggage on way from Chicago back to Portland. Agent lied to us that an agent had gone down to baggage desk to help us...we were sitting AT the desk the entire time and no one showed up. Now no one is available to discuss location / status of my suitcase, and the ETA. No one answers the phone at the number given to me. Poor, poor customer service.

ORD
PDX
Mediocre 2.6

No sense of urgency

ORD
PDX
Okay 4.6

I like that I was seated in the window seat and that there was space for me to move around in my seat and be able to sleep

the delays in boarding, last minute gate changes, how you have to pay for a drink, no free food at all, which sucks if you are on a budget. I was supposed to be there at 11 but it turned to be 2 am.

Wed, May 9
ORD
PDX
4h 20m
Mon, May 14
PDX
ORD
3h 56m
Trip: 6 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Mediocre 3.0

It took me from point A to point B.

Baggage fees are ridiculous. Never again with Spirit.

ORD
PDX
Mediocre 2.6

It was the same as the first leg of my flight. Not good

The same as the first flight. I will not fly Spirit Airlines ever again.

ORD
PDX
Okay 5.3

Price

Uncomfortable

ORD
PDX
Good 6.4

The flight took off on time, as expected. The crew was super positive and friendly. Boarding went smoothly and quickly.

Seats are small, as expected. Gates switched and it was only announced, never made public on the flight update website.

ORD
PDX
Mediocre 3.3

The crew was great even though the airline was having problems.

The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice.

Tue, Apr 3
ORD
PDX
7h 59m
Sat, Apr 7
PDX
ORD
7h 23m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 27
ORD
PDX
19h 00m
Sat, Mar 3
PDX
ORD
18h 01m
Trip: 5 days
6.3GoodShow reviews
Overall 6.3 Good
Based on 9 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
ORD
PDX
Mediocre 3.6

Extra fees for everything. Worst seats on any plane flown. Delayed with no explanation.

ORD
PDX
Okay 4.3

Frontier charges for everything including snacks. The cost of the flight was actually more expensive after factoring in baggage fees, snacks, and charges to select my seat.

ORD
PDX
Okay 4.0

Middle seat was empty

The delay. No food. No apologies

ORD
PDX
Excellent 8.0

Not a full flight so I had the whole row and it had plenty of leg space. Overall smooth process.

Charging for picking a seat and carry on luggage is ridiculous.

PHL
SJU
Good 6.0

boarding and treatment by staff wad excellent

$3 for a cup of coffee is outrageous.... other airlines at least include beverages and a snack (peanuts etc).

Thu, Mar 22
ORD
PDX
4h 29m
Sun, Apr 29
PDX
ORD
3h 56m
Trip: 39 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 3
MDW
PDX
8h 44m
Tue, Apr 10
PDX
MDW
5h 54m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

MEX
LAX
Excellent 10.0

The Delta flight was such a pleasant contrast to the funky Interjet flight that I took from L.A. to Mexico that my Economy Class felt like First Class.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

Sat, Jun 2
ORD
PDX
4h 20m
Sat, Jun 9
PDX
ORD
3h 56m
Trip: 8 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Mediocre 2.0

nothing

Everything. I'm never flying Spirit again. My vacation was almost because they have no idea how to run an airline. Plus, their baggage fees are ridiculous. I'm telling everybody I know to never fly Spirit.

ORD
PDX
Good 6.4

The flight took off on time, as expected. The crew was super positive and friendly. Boarding went smoothly and quickly.

Seats are small, as expected. Gates switched and it was only announced, never made public on the flight update website.

ORD
PDX
Mediocre 3.0

It took me from point A to point B.

Baggage fees are ridiculous. Never again with Spirit.

ORD
PDX
Mediocre 2.6

It was the same as the first leg of my flight. Not good

The same as the first flight. I will not fly Spirit Airlines ever again.

ORD
PDX
Mediocre 3.3

The crew was great even though the airline was having problems.

The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice.

Tue, May 1
MDW
PDX
6h 06m
Tue, May 8
PDX
MDW
8h 20m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

Tue, Jun 5
ORD
PDX
4h 20m
Mon, Jun 11
PDX
ORD
3h 56m
Trip: 7 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Mediocre 2.6

It was the same as the first leg of my flight. Not good

The same as the first flight. I will not fly Spirit Airlines ever again.

ORD
PDX
Okay 4.6

I like that I was seated in the window seat and that there was space for me to move around in my seat and be able to sleep

the delays in boarding, last minute gate changes, how you have to pay for a drink, no free food at all, which sucks if you are on a budget. I was supposed to be there at 11 but it turned to be 2 am.

ORD
PDX
Mediocre 2.0

Flight from Dallas to Chicago was delayed 2.5 hours, so they pulled me off the plane when it was finally time to board, telling me id miss my connecting flight. There needs to be a better way to handle that, the level of inconvenience set upon me was massive.

ORD
PDX
Mediocre 3.3

The crew was great even though the airline was having problems.

The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice.

ORD
PDX
Okay 5.5

The airplanes seemed new, and the flight back was on time.

Primarily the pricing is deceptive because things that included in the ticket price on most major airlines (e.g., 1 carry-on bag, a seat on the plane, soft drinks) must be paid for after buying the ticket. Fees just for a carry-on bag and selecting a seat on the plane added up to nearly $130 over the advertised ticket, and would have been more had I not checked in before leaving for the airport.

Fri, Jun 1
MDW
PDX
6h 07m
Sat, Jun 2
PDX
MDW
8h 10m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

Wed, Jul 11
ORD
PDX
4h 24m
Tue, Jul 17
PDX
ORD
3h 57m
Trip: 7 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Good 6.4

The flight took off on time, as expected. The crew was super positive and friendly. Boarding went smoothly and quickly.

Seats are small, as expected. Gates switched and it was only announced, never made public on the flight update website.

ORD
PDX
Okay 4.0

2 hours late leaving chicago

ORD
PDX
Mediocre 3.3

The crew was great even though the airline was having problems.

The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice.

ORD
PDX
Mediocre 2.0

Flight from Dallas to Chicago was delayed 2.5 hours, so they pulled me off the plane when it was finally time to board, telling me id miss my connecting flight. There needs to be a better way to handle that, the level of inconvenience set upon me was massive.

ORD
PDX
Okay 4.6

I like that I was seated in the window seat and that there was space for me to move around in my seat and be able to sleep

the delays in boarding, last minute gate changes, how you have to pay for a drink, no free food at all, which sucks if you are on a budget. I was supposed to be there at 11 but it turned to be 2 am.

Mon, Jul 9
ORD
PDX
8h 34m
Wed, Jul 11
PDX
ORD
8h 41m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

JFK
LAX
Excellent 10.0

The in flight entertainment was superb.

I have no complaints.

MEX
LAX
Excellent 10.0

The Delta flight was such a pleasant contrast to the funky Interjet flight that I took from L.A. to Mexico that my Economy Class felt like First Class.

ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

Wed, Aug 1
ORD
PDX
4h 24m
Wed, Aug 8
PDX
ORD
3h 57m
Trip: 8 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PDX
Mediocre 3.3

The crew was great even though the airline was having problems.

The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice.

ORD
PDX
Okay 5.3

Price

Uncomfortable

ORD
PDX
Mediocre 2.6

It was the same as the first leg of my flight. Not good

The same as the first flight. I will not fly Spirit Airlines ever again.

ORD
PDX
Mediocre 2.0

Flight from Dallas to Chicago was delayed 2.5 hours, so they pulled me off the plane when it was finally time to board, telling me id miss my connecting flight. There needs to be a better way to handle that, the level of inconvenience set upon me was massive.

ORD
PDX
Mediocre 2.6

No sense of urgency

Show more results

Chicago to Portland Flight Information

Avg. Flight Duration 4h 09m
Flights Arrive in Portland
Flights Depart from Chicago
Flight Price $157
Distance 1750 miles
Airlines Spirit Airlines, Frontier, Delta, Virgin America
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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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.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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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.