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

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Good to Know

Low Season:
August
Best time to beat the crowds
2%
expected price decrease
High Season:
March
Most popular time to fly
7%
expected price increase
Average Price:
$298
(avg. price over the last 2 weeks)
Good Deal:
$215
or less (round trip)

When to Book Flights from Portland to Chicago

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 $214 or less.
The cheapest flight from Portland to Chicago was found 25 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 February, March and April. The cheapest month to fly is August.
Morning departure is around 17% 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 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 1750 miles.
How many flights are there between Portland and Chicago?
There are 316 (nonstop) flights between Portland and Chicago per week, averaging 48 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 Spirit Airlines ($138), Frontier ($219) and Multiple Airlines ($222).
Do I need a passport to fly between Portland and Chicago?
No.
Which airlines fly most frequently between Portland and Chicago?
United (7 times daily), Alaska Airlines (5 times daily), Southwest (4 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, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago back to Portland, the best deals are generally found on Thursday, with Friday being the most expensive.

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

Airports
Origin
Portland
$138
only
$138
Destination
Chicago
$138
only
$138
$266
only
$266
Tue, Mar 6
PDX
ORD
6h 39m
Tue, Mar 13
ORD
PDX
7h 59m
Trip: 7 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

Mon, Feb 26
PDX
ORD
17h 53m
Wed, Feb 28
ORD
PDX
15h 45m
Trip: 3 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 14 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PHX
MKE
Okay 4.0

Nothing

Everything

PDX
ORD
Good 6.0

Fare

Uncomfortable seating and armrest design was pathetic boarding on cruel and unusual punishment.

PDX
ORD
Excellent 9.0

Great Service, On time.

Seats are pretty thin cushioned

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).

PDX
ORD
Excellent 10.0

Everything was good

Wed, Mar 28
PDX
ORD
4h 04m
Sat, Apr 28
ORD
PDX
4h 20m
Trip: 32 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 20
PDX
ORD
4h 04m
Wed, Mar 28
ORD
PDX
4h 29m
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 18790 reviews
Overall
8.3
Boarding
8.4
Comfort
8.2
Crew
8.5
Entertainment
8.1
Food
7.7
SFO
EWR
Excellent 10.0

The flt was totally full, yet the crew took care of everyone really well.

Crew and pilot got on the PA 6 times from the time I Sat down till take off, which is too much. That irritated me a lot. They got on the PA to make the usual announcements during the remainder of the flt, which was normal.

SFO
SEA
Okay 4.8

We didn't crash.

We had to wait 1.5 for the pilots to arrive....after we boarded the plane. The air was not working on the ground, so the plane was about 80 degrees.

JFK
LAX
Good 6.4

cool mood lightings

crew seemed very passive

LAS
JFK
Excellent 10.0

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

No complaints.

SFO
DAL
Excellent 8.0

comfortable seats and TV everyseat plus wifi texting

Aircraft A319 did not have charging USB port not even peanuts, all food was pay even thought it was a through flight and same plane, they made us get off at Dallas

Tue, Mar 20
PDX
MDW
5h 40m
Tue, Mar 27
MDW
PDX
6h 24m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

Tue, Feb 27
PDX
ORD
6h 39m
Tue, Mar 6
ORD
PDX
7h 57m
Trip: 8 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

Thu, Apr 12
PDX
ORD
3h 56m
Sun, Apr 15
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

Sat, Jul 14
PDX
ORD
3h 53m
Thu, Jul 19
ORD
PDX
8h 12m
Trip: 6 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 113 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
PDX
ORD
Okay 4.0

I liked that they gave us blankets. It was cold when we boarded.

I was put into a very uncomfortable situation when we finally got boarded and situated in our seats. I was in the window seat of a three seat row. The two men in the center and aisle seats knew each other and struck up a little conversation during boarding but it was a late flight and I was gearing up for some sleep in my seat. I fell asleep after take off and when I woke up the guy in the center seat had taken his shirt off and nearly had his pants down to his knees. Him and his buddy were both asleep, but half-naked-man was a much more mobile sleeper and was constantly rolling his head onto my shoulder to sleep on which I pushed him off many times. Now, someone accidentally falling asleep on you on a plane is one thing; a half-naked-man rolling his body onto yours is a complete other thing. I couldn't really get him to wake when I was pushing him off me so I was kind of hoping someone was gonna come by and tell him to get his clothes back on and pull it together; that never happened. On top of not being able to keep his own body in his own seat he must have been having a very interesting dream because he was having a hard time keeping his hands off of his private parts. Being a man, I was not incredibly grossed out by this (although not what I want to be seeing when I'm on a flight), but it doesn't make it any less sexually offensive. I don't fly that often but I find it hard to be believe that this could be considered acceptable behavior to be tolerated when paying for a plane ticket. To cap it all off, when we were landing and the flight attendants were roaming the aisles to check seat belts and stuff, no one seemed to care that this guy was topless and touching himself. One Flight Attendant asked his friend (the guy in the aisle) to tell him to "prepare to land" which he didn't do. It wasn't till we landed and the seat belt sign went off that his friend woke him up and he put his clothes back on. They had a good chuckle about it as if nothing happened. Kind of put me out. I took a picture of them in full slumber with his clothes off if you guys want evidence.

PDX
ORD
Good 7.0

Good service.

The website is pretty bad, not user friendly. Took several times for things to take, and was a frustrating experience. Luftansa's website. Not United.

PDX
ORD
Okay 4.3

Didn't crash

Get my to my destination on time. I missed my connection and will be 5 hours late to my destination, missing most of Father's Day

PDX
ORD
Mediocre 2.6

Nothing

United changed my 10 am reservation to 6:40 which meant, in addition to getting up at 4 am, missing a great free breakfast at my hotel, that I had to spend $55 on a cab rather than take public transportation to the airport. Further more, the 4+ hour layover at Newark (horrible terminal) led to 6+ hours. Arrived home at the end of an 18 hour day barely functioning.

PDX
ORD
Good 7.0

Both flights were late, seriously late.

Wed, Apr 25
PDX
ORD
3h 56m
Sat, Apr 28
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

Mon, Apr 30
PDX
ORD
3h 56m
Wed, May 16
ORD
PDX
4h 20m
Trip: 17 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

Thu, May 3
PDX
ORD
3h 56m
Sun, May 6
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

Wed, May 30
PDX
ORD
4h 11m
Thu, Jun 7
ORD
PDX
4h 20m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 3
PDX
ORD
3h 56m
Sun, May 6
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Good 6.0

The price

Impossible to sleep

Tue, Apr 10
PDX
MDW
5h 54m
Tue, Apr 17
MDW
PDX
6h 25m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
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

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

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.

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

Sat, Apr 21
PDX
ORD
3h 56m
Mon, Apr 23
ORD
PDX
4h 20m
Trip: 3 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

Tue, Apr 10
PDX
MDW
8h 54m
Wed, Apr 11
MDW
PDX
8h 46m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

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.

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

Fri, May 4
PDX
ORD
3h 56m
Mon, May 7
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Good 6.0

The price

Impossible to sleep

Wed, Apr 4
PDX
ORD
4h 04m
Sun, Apr 8
ORD
PDX
7h 06m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 12
PDX
MDW
8h 53m
Mon, Jun 18
MDW
PDX
6h 03m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

ATL
SLC
Excellent 10.0

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

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

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.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

Fri, May 4
PDX
MDW
7h 30m
Wed, May 9
MDW
PDX
8h 48m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

VPS
ATL
Good 7.3

Quick boarding. Nice crew. No food or entertainment so I couldn't rate those. N/A should be a choice

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

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
IND
Excellent 10.0

The comfort, space, quiet, snacks

Show more results

Portland to Chicago Flight Information

Avg. Flight Duration 4h 10m
Flights Arrive in Chicago
Flights Depart from Portland
Flight Price $138
Distance 1750 miles
Airlines Spirit Airlines, Frontier, Virgin America, Delta, United
*
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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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.

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.