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

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Looking for a cheap flight? 25% of our users found flights on this route for $393 or less.

FAQs for Booking Chicago Midway to Portland Flights

How long does a flight from Chicago Midway to Portland take?
An average nonstop flight takes 4h 16m, covering a distance of 893 miles.
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 ($339)
Do I need a passport to fly between Chicago Midway and Portland?
No.
What’s the cheapest day of the week to fly Chicago Midway to Portland?
For Chicago Midway to Portland, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Portland back to Chicago Midway, the best deals are generally found on Friday, with Thursday being the most expensive.

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

Airports
Origin
Chicago
$339
only
$339
Destination
Portland
$339
only
$339
Wed, Feb 14
MDW
PWM
10h 38m
Wed, Feb 28
PWM
MDW
10h 19m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
RSW
Good 6.3

Quick boarding, clean plane, good entertainment system.

Used a neck/back pillow and jacket against hull to try and keep my shoulder and arm from freezing solid. I usually sit by the window on a couple dozen flights per year, and it has never been this cold on my arm. I wonder if a heating pad would work on their outlet?

LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

CUN
JFK
Okay 4.6

Delta seats are comfortable and media ststem is good.

Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something.

SEA
PDX
Excellent 9.6

Seats a bit cramped

Mon, May 7
MDW
PWM
5h 34m
Tue, May 22
PWM
MDW
4h 22m
Trip: 16 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MBJ
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

CUN
JFK
Okay 4.6

Delta seats are comfortable and media ststem is good.

Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something.

MSP
RSW
Good 6.3

Quick boarding, clean plane, good entertainment system.

Used a neck/back pillow and jacket against hull to try and keep my shoulder and arm from freezing solid. I usually sit by the window on a couple dozen flights per year, and it has never been this cold on my arm. I wonder if a heating pad would work on their outlet?

LAS
SLC
Good 6.0

the seats were ok

was little late

SEA
PDX
Excellent 9.6

Seats a bit cramped

Fri, Jun 1
MDW
PWM
4h 16m
Wed, Jun 6
PWM
MDW
6h 33m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAS
SLC
Good 6.0

the seats were ok

was little late

CUN
JFK
Okay 4.6

Delta seats are comfortable and media ststem is good.

Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something.

SEA
PDX
Excellent 9.6

Seats a bit cramped

LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

ATL
SMF
Excellent 10.0

Anna from South Africa was funny, and super accomidatinf

Wed, Jul 25
MDW
PWM
5h 05m
Wed, Aug 1
PWM
MDW
6h 40m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ANC
SEA
Excellent 10.0

Delta has great seats, friendly employees and engaged managers and pilots. Even their customer service Center reaches out to help on suggestions. I am flying to Portland for School over 40 round trips and I am saving $4,000 vs Alaska Air. Plus I get miles and discounts with the Delta Amex Card. I am very pleased.

I don’t like harsh change in schedule fees but it forces me to plan. I wish the Seattle to Portland Eve flight landed in time to catch Portland Rail system at 11:50 PM

CUN
JFK
Okay 4.6

Delta seats are comfortable and media ststem is good.

Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something.

RDU
LAX
Excellent 8.4

Punctual departures. Adequate overheard space.

Food was mediocre for a 5-6 hour flight. I expected a little bit more.

MSP
RSW
Good 6.3

Quick boarding, clean plane, good entertainment system.

Used a neck/back pillow and jacket against hull to try and keep my shoulder and arm from freezing solid. I usually sit by the window on a couple dozen flights per year, and it has never been this cold on my arm. I wonder if a heating pad would work on their outlet?

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

Fri, Mar 2
MDW
PWM
5h 32m
Sat, Mar 10
PWM
MDW
4h 38m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
PDX
Excellent 9.6

Seats a bit cramped

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

ATL
MBJ
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

RDU
LAX
Excellent 8.4

Punctual departures. Adequate overheard space.

Food was mediocre for a 5-6 hour flight. I expected a little bit more.

Sat, Jun 9
MDW
PWM
6h 55m
Mon, Jun 11
PWM
MDW
8h 52m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

ATL
SMF
Excellent 10.0

Anna from South Africa was funny, and super accomidatinf

CUN
JFK
Okay 4.6

Delta seats are comfortable and media ststem is good.

Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something.

RDU
LAX
Excellent 8.4

Punctual departures. Adequate overheard space.

Food was mediocre for a 5-6 hour flight. I expected a little bit more.

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

Fri, Feb 16
MDW
PWM
5h 35m
Sun, Feb 18
PWM
MDW
4h 50m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAS
SLC
Good 6.0

the seats were ok

was little late

ATL
SMF
Excellent 10.0

Anna from South Africa was funny, and super accomidatinf

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

CUN
JFK
Okay 4.6

Delta seats are comfortable and media ststem is good.

Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something.

LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

Fri, Jan 26
MDW
PWM
7h 22m
Sun, Jan 28
PWM
MDW
7h 29m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15342 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
PDX
Excellent 9.6

Seats a bit cramped

MSP
RSW
Good 6.3

Quick boarding, clean plane, good entertainment system.

Used a neck/back pillow and jacket against hull to try and keep my shoulder and arm from freezing solid. I usually sit by the window on a couple dozen flights per year, and it has never been this cold on my arm. I wonder if a heating pad would work on their outlet?

ANC
SEA
Excellent 10.0

Delta has great seats, friendly employees and engaged managers and pilots. Even their customer service Center reaches out to help on suggestions. I am flying to Portland for School over 40 round trips and I am saving $4,000 vs Alaska Air. Plus I get miles and discounts with the Delta Amex Card. I am very pleased.

I don’t like harsh change in schedule fees but it forces me to plan. I wish the Seattle to Portland Eve flight landed in time to catch Portland Rail system at 11:50 PM

RDU
LAX
Excellent 8.4

Punctual departures. Adequate overheard space.

Food was mediocre for a 5-6 hour flight. I expected a little bit more.

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

Chicago Midway to Portland Flight Information

Flights Arrive in Portland
Flights Depart from Chicago Midway
Flight Price $339
Distance 893 miles
Airlines Delta
*
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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.