Find Cheap Flights from Chicago Midway to Portland (MDW - PDX)

Search hundreds of travel sites at once for deals on flights to Portland

Thu 11/23
Thu 11/30
Any month
Compare vs. KAYAK |

Good to Know

Average Price:
$393
(avg. price over the last 2 weeks)
Good Deal:
$279
or less (round trip)

When to Book Flights from Chicago Midway 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 $279 or less.
The cheapest flight from Chicago Midway to Portland was found 83 days before departure, on average.
Book at least 7 weeks before departure in order to get a below-average price.
Morning departure is around 2% 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 Midway to Portland Flights

How long does a flight from Chicago Midway to Portland take?
An average nonstop flight takes 6h 06m, covering a distance of 1747 miles.
How many flights are there between Chicago Midway and Portland?
There are 29 (nonstop) flights between Chicago Midway and Portland per week, averaging 4 per day.
Which airlines provide the cheapest flights from Chicago Midway to Portland?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($294)
Do I need a passport to fly between Chicago Midway and Portland?
No.
Which airlines fly most frequently between Chicago Midway and Portland?
Southwest (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Portland?
For Chicago Midway to Portland, Saturday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Portland back to Chicago Midway, the best deals are generally found on Saturday, with Thursday being the most expensive.

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

Airports
Origin
Chicago
$294
only
$294
Destination
Portland
$294
only
$294
Sat, Jan 13
MDW
PDX
6h 09m
Fri, Jan 19
PDX
MDW
5h 53m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Tue, Jan 16
MDW
PDX
6h 28m
Mon, Jan 22
PDX
MDW
7h 00m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

Fri, Feb 2
MDW
PDX
9h 05m
Mon, Feb 5
PDX
MDW
8h 20m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

Sat, Feb 10
MDW
PDX
6h 29m
Wed, Feb 14
PDX
MDW
7h 30m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OMA
ATL
Good 7.6

My comfort zone seat

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Thu, Feb 22
MDW
PDX
6h 06m
Tue, Feb 27
PDX
MDW
5h 27m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OMA
ATL
Good 7.6

My comfort zone seat

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Fri, Mar 2
MDW
PDX
6h 27m
Sun, Mar 4
PDX
MDW
6h 31m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

Sat, Mar 3
MDW
PDX
6h 11m
Tue, Mar 6
PDX
MDW
5h 27m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

OMA
ATL
Good 7.6

My comfort zone seat

Wed, Apr 18
MDW
PDX
6h 06m
Tue, Apr 24
PDX
MDW
5h 27m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

Wed, May 2
MDW
PDX
6h 06m
Tue, May 8
PDX
MDW
5h 53m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

Wed, May 9
MDW
PDX
6h 06m
Wed, May 16
PDX
MDW
8h 33m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

Tue, Dec 5
MDW
PDX
9h 48m
Tue, Dec 12
PDX
MDW
5h 49m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

OMA
ATL
Good 7.6

My comfort zone seat

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

Wed, Nov 29
MDW
PDX
10h 38m
Mon, Dec 4
PDX
MDW
8h 50m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

OMA
ATL
Good 7.6

My comfort zone seat

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

Tue, Dec 5
MDW
PDX
9h 01m
Sun, Dec 10
PDX
MDW
5h 35m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Mon, Apr 23
MDW
PDX
8h 43m
Sun, Apr 29
PDX
MDW
8h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

Sat, Mar 24
MDW
PDX
8h 53m
Thu, Mar 29
PDX
MDW
5h 57m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
ATL
Good 6.6

On the MSP to ATL leg the gate crew made a huge deal about checking rolling bags. They even stopped us at check-in and nearly begged us to check our bags pointing to the backed up jetway. But we had a lot of unpacking to do before checking our bags so we politely declined three times. On getting to our seats there were at least 8 open slots for bags near us. I heard a crew member call forward to say "tell them no more rollaboards" so they forced everyone left to check. On departure they slammed shut several very large empty overheads. WTF

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

Fri, Nov 24
MDW
PDX
6h 22m
Sun, Nov 26
PDX
MDW
8h 06m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

SFO
SEA
Excellent 10.0

The t.v. 's at each seat

Nothing

OMA
ATL
Good 7.6

My comfort zone seat

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

Wed, Dec 27
MDW
PDX
8h 52m
Sat, Dec 30
PDX
MDW
7h 17m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13658 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

CVG
BOS
Good 7.0

Friendly crew with modern plane

Why am I paying for first class for just snacks I can buy in an airport shop?

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

Show more results
*
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:

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

We compile tonnes of data for you
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.

^
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.