Cheap Flight Tickets from Chicago (MDW) to Portland (PDX), Starting at $488

Good to Know: Cheapest and Fastest MDW - PDX Flights

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

Cheapest Round Trip Flight

$488

WN Southwest Airlines • nonstop • 6h 50m

Aug 31 – Aug 31

The cheapest round trip flight from Chicago to Portland (MDW-PDX-MDW) is currently $488

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Cheapest Direct Flight

$488

WN Southwest Airlines • nonstop • 6h 50m

Aug 31

The cheapest nonstop flight from Chicago to Portland (MDW-PDX) is currently $488

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Fastest Flight

6h 50m

The fastest nonstop flight from Chicago to Portland (MDW-PDX) takes 6h 50m

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

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

Aug 31 - Aug 31, Economy
WN
Chicago → Portland
6h 50m
10:40 AM - 12:50 PM • nonstop
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$488
Southwest Airlines
Aug 31 - Aug 31, Economy
WN
Chicago → Portland
11h 55m
5:40 AM - 10:55 AM • 1 stop
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$498
Southwest Airlines
Aug 31 - Aug 31, Economy
WN
Chicago → Portland
23h 25m
7:10 AM - 7:15 PM • 1 stop
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$498
Southwest Airlines
Aug 31 - Aug 31, Economy
WN
Chicago → Portland
13h 35m
10:20 AM - 4:35 PM • 1 stop
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$498
Southwest Airlines
Aug 31 - Aug 31, Economy
WN
Chicago → Portland
17h 10m
6:15 AM - 2:45 PM • 2 stops
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$503
Southwest Airlines
Aug 31 - Aug 31, Economy
WN
Chicago → Portland
10h 45m
5:30 AM - 10:15 AM • 1 stop
WN
Chicago → Portland
20h 15m
7:35 PM - 9:50 AM • 1 stop
$507
Southwest Airlines

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

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

FAQs on Chicago to Portland Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to PDX?
The most popular airline flying from Chicago to Portland are
Can I fly from MDW to PDX non-stop?
Yes, you can fly MDW to PDX non-stop on
Which airlines fly nonstop between Chicago and Portland?
The non-stop flights between Chicago and Portland are .
What’s the earliest departure time from MDW to PDX Airport?
The earliest flight leaves MDW at 5:30 am and lands in PDX - Portland International
What are the airports in Portland?
PDX
Can I make changes to my Chicago to Portland 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 MDW to PDX?
Read the fare rules of the Chicago to Portland 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 Chicago and Portland?
operate flights between Chicago and Portland
How long does a flight from Chicago to Portland take?
It takes approximately 4 hour to fly non-stop from MDW to PDX, which is 1751.25 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Portland (PDX) ?
In the past couple of days, the cheapest tickets to PDX from MDW were found on WN : USD 503
Do I need a passport to fly between MDW and PDX?
No
What’s the latest departure time from MDW to PDX ?
The last flight leaves MDW at 10:40 am

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

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Portland International , Portland, US
Distance 1751 miles

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