Cheap Flight Tickets from Portland (PWM) to Chicago (MDW), Starting at $213

Good to Know: Cheapest and Fastest PWM - MDW Flights

Useful information for finding best airline tickets from Portland International Jetport to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$304

WN Southwest Airlines • 2 stops • 10h 20m

Jul 23 – Aug 13

The cheapest round trip flight from Portland to Chicago (PWM-MDW-PWM) is currently $304

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Cheapest Direct Flight

$213

WN Southwest Airlines • nonstop • 3h 55m

Jul 07

The cheapest nonstop flight from Portland to Chicago (PWM-MDW) is currently $213

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Fastest Flight

3h 55m

The fastest nonstop flight from Portland to Chicago (PWM-MDW) takes 3h 55m

Latest Flight Deals from Portland (PWM) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Portland to Chicago. Ideal for travelers with confirmed return itineraries.

Jul 23 - Aug 13, Economy
WN
Portland → Chicago
10h 20m
3:20 PM - 8:40 PM • 2 stops
WN
Portland → Chicago
9h 15m
8:05 AM - 3:00 PM • 2 stops
$304
Southwest Airlines
Jul 23 - Aug 13, Economy
WN
Portland → Chicago
19h 5m
5:35 AM - 4:20 PM • 2 stops
WN
Portland → Chicago
3h 40m
6:10 PM - 9:30 PM • nonstop
$420
Southwest Airlines
Jul 23 - Aug 13, Economy
WN
Portland → Chicago
10h 25m
3:20 PM - 8:45 PM • 2 stops
WN
Portland → Chicago
21h 50m
7:40 PM - 9:50 AM • 2 stops
$431
Southwest Airlines
Jul 23 - Aug 13, Economy
WN
Portland → Chicago
13h 50m
10:25 AM - 5:55 PM • 2 stops
WN
Portland → Chicago
21h 50m
7:40 PM - 9:50 AM • 2 stops
$482
Southwest Airlines
Jul 23 - Aug 13, Economy
WN
Portland → Chicago
17h 35m
10:25 AM - 8:20 PM • 2 stops
WN
Portland → Chicago
21h 50m
7:40 PM - 9:50 AM • 2 stops
$482
Southwest Airlines
Jul 23 - Aug 13, Economy
WN
Portland → Chicago
10h
5:35 AM - 10:35 AM • 1 stop
WN
Portland → Chicago
8h 20m
9:00 AM - 3:00 PM • 1 stop
$486
Southwest Airlines

Fly from Portland to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Portland to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Portland to Chicago Flights

What are the airports in Portland?
PWM
What’s the most popular airline flying from PWM to MDW?
The most popular airline flying from Portland to Chicago are
Can I fly from PWM to MDW non-stop?
Yes, you can fly PWM to MDW non-stop on
Which airlines fly nonstop between Portland and Chicago?
The non-stop flights between Portland and Chicago are .
What’s the earliest departure time from PWM to MDW Airport?
The earliest flight leaves PWM at 5:35 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Portland to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from PWM to MDW?
Read the fare rules of the Portland to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Portland and Chicago?
operate flights between Portland and Chicago
How long does a flight from Portland to Chicago take?
It takes approximately 2 hour to fly non-stop from PWM to MDW, which is 895.38 miles by air.
Which airlines provide the cheapest flights from Portland (PWM) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from PWM were found on WN : USD 420
Do I need a passport to fly between PWM and MDW?
No
What’s the latest departure time from PWM to MDW ?
The last flight leaves PWM at 3:20 pm

Portland (PWM) to Chicago (MDW): Airport Information

Origin Airport Portland International Jetport , Portland, US
Destination Airport Chicago Midway International , Chicago, US
Distance 895 miles

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