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

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Sat 11/25
Sat 12/2
Any month
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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 1% 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 17m, covering a distance of 1750 miles.
How many flights are there between Chicago and Portland?
There are 343 (nonstop) flights between Chicago and Portland per week, averaging 53 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 Frontier ($160), Alaska Airlines ($197) and Spirit Airlines ($204).
Do I need a passport to fly between Chicago and Portland?
No.
Which airlines fly most frequently between Chicago and Portland?
United (12 times daily), Aer Lingus (5 times daily), Southwest (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, Monday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Portland back to Chicago, the best deals are generally found on Monday, with Wednesday being the most expensive.

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

Airports
Origin
Chicago
$160
only
$160
Destination
Portland
$160
only
$160
Mon, Jan 8
ORD
PDX
15h 45m
Tue, Jan 16
PDX
ORD
21h 08m
Trip: 9 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 4.3

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.

DEN
RNO
Excellent 10.0

Very efficient boarding. Although I thought it strange at first that Frontier charges for overhead storage, the storage situation was roomy even with a full flight.

MSP
RSW
Mediocre 3.0

Flight was smooth

Crew did basically nothing but talk among themselves. Didn’t pick up garbage till the last minute. Many passengers took up their own garbage.

CMH
DEN
Excellent 10.0

Cheap; smooth landing

Screaming children; no leg room

MSY
AUS
Okay 4.3

I arrived 2 hours before my scheduled flight time but had to wait for at least 15 minutes before anyone came to the counter.

Sat, Feb 3
ORD
PDX
4h 36m
Sat, Feb 10
PDX
ORD
3h 50m
Trip: 8 days
9.2ExcellentShow reviews
Overall 9.2 Excellent
Based on 46 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.8
Food
8.0
ORD
PDX
Excellent 10.0

Free movies!

ORD
PDX
Excellent 10.0

The crew was fantastic! I was on my way to my bachelorette party in Portland and they were so sweet, congratulating me and even giving my friends and I free drinks! I would definitely fly them again! LOVED IT! :)

ORD
PDX
Excellent 10.0

On time did not have to wait long at all for luggage.

ORD
PDX
Excellent 10.0

On-time....Just a typical flight

No food served in flight even if it is dinner time flight. May be i am expecting too much as i took this as connecting flight after my 2 international flights.No entertainment. Common TV for 3-4 rows and video was stopped after 1 hour.

ORD
PDX
Excellent 8.6

Good customer service and comfortable plane

Sat for an hour before take off.

Tue, May 15
ORD
PDX
10h 19m
Sun, May 20
PDX
ORD
4h 01m
Trip: 6 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
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 2.6

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.

ORD
PDX
Mediocre 2.6

No sense of urgency

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.

Thu, Dec 7
ORD
PDX
7h 56m
Tue, Dec 12
PDX
ORD
21h 13m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 9
ORD
PDX
19h 00m
Sat, Jan 13
PDX
ORD
7h 10m
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
LAS
STL
Mediocre 2.0

NOTHING!!!!!!

I booked a flight with them for the Thanksgiving holiday.... I was supposed to travel Wednesday 22 - Saturday to STLand back... I was IMMEDIATELY shocked by only being able to carry 1 personal item... When I found out exactly how small 45 centimeters was...I tried to cancel the trip & be refunded within 5-6 hours.... They told me to fill out a form & return it to them... THEY WERE SUPPOSED TO GET BACK TO ME WITHIN HOURS TO NOTIFY OF THE REFUND AMOUNT & NOT...I REPEAT NOT ACTUALLY CANCEL THE TRIP UNLESS I AGREED TO THE REFUND AMOUNT... I never heard anything from them! I just assumed it was just taking forever for them to approve my refund... Therefore...assuming that the flight was still booked...SINCE I never APPROVED ANY REFUND... I visited kiwi.com several times before the the trip & there was ABSOLUTELY NOTHING informing me of any trip cancellation... I went to the airport... Wasn’t able to board... Talked to kiwi.on the phone... Didn’t find out the trip was canceled until after the boarding was closed for that flight. Ceddrick Jonae bayfunk@yahoo.com 415-322-9515 kiwi.com booking number: 4709776 Reservation number (PNR): MEUOOZ E-ticket: 984-7069682518

ORD
PDX
Okay 4.0

Middle seat was empty

The delay. No food. No apologies

LAS
BNA
Good 7.6

Friendliness and efficiency.

No Wifi. Very little room for anything. Tiny tray tables.

CMH
DEN
Excellent 10.0

Cheap; smooth landing

Screaming children; no leg room

ORD
PDX
Excellent 10.0

The crew was nice and fun

Wed, Jan 10
ORD
PDX
8h 46m
Tue, Jan 16
PDX
ORD
21h 08m
Trip: 7 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
LAS
BNA
Good 7.6

Friendliness and efficiency.

No Wifi. Very little room for anything. Tiny tray tables.

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.

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.

LAS
STL
Mediocre 2.0

NOTHING!!!!!!

I booked a flight with them for the Thanksgiving holiday.... I was supposed to travel Wednesday 22 - Saturday to STLand back... I was IMMEDIATELY shocked by only being able to carry 1 personal item... When I found out exactly how small 45 centimeters was...I tried to cancel the trip & be refunded within 5-6 hours.... They told me to fill out a form & return it to them... THEY WERE SUPPOSED TO GET BACK TO ME WITHIN HOURS TO NOTIFY OF THE REFUND AMOUNT & NOT...I REPEAT NOT ACTUALLY CANCEL THE TRIP UNLESS I AGREED TO THE REFUND AMOUNT... I never heard anything from them! I just assumed it was just taking forever for them to approve my refund... Therefore...assuming that the flight was still booked...SINCE I never APPROVED ANY REFUND... I visited kiwi.com several times before the the trip & there was ABSOLUTELY NOTHING informing me of any trip cancellation... I went to the airport... Wasn’t able to board... Talked to kiwi.on the phone... Didn’t find out the trip was canceled until after the boarding was closed for that flight. Ceddrick Jonae bayfunk@yahoo.com 415-322-9515 kiwi.com booking number: 4709776 Reservation number (PNR): MEUOOZ E-ticket: 984-7069682518

Tue, Jan 16
ORD
PDX
19h 00m
Thu, Jan 18
PDX
ORD
10h 25m
Trip: 3 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
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.

DEN
RNO
Excellent 10.0

Very efficient boarding. Although I thought it strange at first that Frontier charges for overhead storage, the storage situation was roomy even with a full flight.

CMH
DEN
Excellent 10.0

Cheap; smooth landing

Screaming children; no leg room

MSP
RSW
Mediocre 3.0

Flight was smooth

Crew did basically nothing but talk among themselves. Didn’t pick up garbage till the last minute. Many passengers took up their own garbage.

Tue, Feb 6
ORD
PDX
4h 40m
Sat, Feb 10
PDX
ORD
3h 50m
Trip: 5 days
9.2ExcellentShow reviews
Overall 9.2 Excellent
Based on 46 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.8
Food
8.0
ORD
PDX
Excellent 10.0

The crew was fantastic! I was on my way to my bachelorette party in Portland and they were so sweet, congratulating me and even giving my friends and I free drinks! I would definitely fly them again! LOVED IT! :)

ORD
PDX
Excellent 10.0

On time did not have to wait long at all for luggage.

ORD
PDX
Excellent 8.0

Flight crew

Delay

ORD
PDX
Excellent 10.0

Flight on time. Great service

ORD
PDX
Excellent 10.0

Free movies!

Thu, Jan 25
ORD
PDX
20h 22m
Tue, Jan 30
PDX
ORD
21h 08m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Apr 27
ORD
PDX
4h 17m
Sun, Apr 29
PDX
ORD
4h 01m
Trip: 3 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.6
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
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
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 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.

Tue, Jan 23
ORD
PDX
19h 00m
Sat, Jan 27
PDX
ORD
7h 10m
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
DEN
RNO
Excellent 10.0

Very efficient boarding. Although I thought it strange at first that Frontier charges for overhead storage, the storage situation was roomy even with a full flight.

MSP
RSW
Mediocre 3.0

Flight was smooth

Crew did basically nothing but talk among themselves. Didn’t pick up garbage till the last minute. Many passengers took up their own garbage.

LAS
BNA
Good 7.6

Friendliness and efficiency.

No Wifi. Very little room for anything. Tiny tray tables.

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.

MSY
AUS
Okay 4.3

I arrived 2 hours before my scheduled flight time but had to wait for at least 15 minutes before anyone came to the counter.

Tue, Dec 5
ORD
PDX
27h 33m
Tue, Dec 12
PDX
ORD
21h 13m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Feb 5
ORD
PDX
15h 45m
Wed, Feb 7
PDX
ORD
17h 53m
Trip: 3 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
CMH
DEN
Excellent 10.0

Cheap; smooth landing

Screaming children; no leg room

ORD
PDX
Okay 4.0

Middle seat was empty

The delay. No food. No apologies

DEN
RNO
Excellent 10.0

Very efficient boarding. Although I thought it strange at first that Frontier charges for overhead storage, the storage situation was roomy even with a full flight.

MSY
AUS
Okay 4.3

I arrived 2 hours before my scheduled flight time but had to wait for at least 15 minutes before anyone came to the counter.

MSP
RSW
Mediocre 3.0

Flight was smooth

Crew did basically nothing but talk among themselves. Didn’t pick up garbage till the last minute. Many passengers took up their own garbage.

Tue, Jan 16
ORD
PDX
7h 59m
Mon, Jan 29
PDX
ORD
12h 56m
Trip: 14 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
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
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.

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
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.

Wed, Dec 13
ORD
PDX
9h 04m
Sun, Dec 31
PDX
ORD
6h 07m
Trip: 19 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Feb 5
ORD
PDX
7h 59m
Tue, Feb 6
PDX
ORD
6h 20m
Trip: 2 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.6
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
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.

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
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 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.

Tue, Jan 9
ORD
PDX
19h 00m
Wed, Jan 10
PDX
ORD
7h 10m
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
Mediocre 3.6

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

LAS
BNA
Good 7.6

Friendliness and efficiency.

No Wifi. Very little room for anything. Tiny tray tables.

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
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.

ORD
PDX
Excellent 10.0

The crew was nice and fun

Fri, Jan 5
ORD
PDX
7h 36m
Wed, Jan 10
PDX
ORD
7h 10m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
ORD
PDX
7h 59m
Mon, Feb 12
PDX
ORD
12h 56m
Trip: 6 days
5.2OkayShow reviews
Overall 5.2 Okay
Based on 153 reviews
Overall
5.6
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
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 2.0

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 2.0

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.

Tue, Feb 6
ORD
PDX
19h 00m
Wed, Feb 7
PDX
ORD
7h 10m
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
MSP
RSW
Mediocre 3.0

Flight was smooth

Crew did basically nothing but talk among themselves. Didn’t pick up garbage till the last minute. Many passengers took up their own garbage.

CMH
DEN
Excellent 10.0

Cheap; smooth landing

Screaming children; no leg room

ORD
PDX
Excellent 10.0

The crew was nice and fun

LAS
BNA
Good 7.6

Friendliness and efficiency.

No Wifi. Very little room for anything. Tiny tray tables.

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.

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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.