Cheap Flight Tickets from Chicago (MDW) to Portland (PDX), Starting at $431

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

$435

DL Delta Airlines • 1 stop •

Jul 05 – Jul 11

The cheapest round trip flight from Chicago to Portland (MDW-PDX-MDW) is currently $435

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Cheapest One way Flight

$510

WN Southwest Airlines • 1 stop • 29h 5m

Jul 06

The cheapest one way flight from Chicago to Portland (MDW-PDX) is currently $510

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Cheapest Direct Flight

$431

WN Southwest Airlines • nonstop • 7h 5m

Jul 05

The cheapest nonstop flight from Chicago to Portland (MDW-PDX) is currently $431

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Fastest Flight

7h

The fastest nonstop flight from Chicago to Portland (MDW-PDX) takes 7h

Top Airlines Flying from Chicago to Portland

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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.

Jul 05 - Jul 11, Economy
DL
Chicago → Portland
- • 1 stop
DL
Chicago → Portland
- • 1 stop
$435
Delta Airlines
Jul 05 - Jul 11, Economy
WN
Chicago → Portland
7h 5m
9:50 PM - 12:15 AM • nonstop
WN
Chicago → Portland
12h 35m
5:15 AM - 3:10 PM • 2 stops
$445
Southwest Airlines
Jul 05 - Jul 11, Economy
WN
Chicago → Portland
15h 40m
6:30 AM - 2:10 PM • 1 stop
WN
Chicago → Portland
9h 10m
2:10 PM - 10:00 PM • 1 stop
$659
Southwest Airlines
Jul 05 - Jul 11, Economy
WN
Chicago → Portland
10h 50m
7:25 AM - 12:15 PM • 1 stop
WN
Chicago → Portland
9h 10m
2:10 PM - 10:00 PM • 1 stop
$742
Southwest Airlines
Jul 05 - Jul 11, Economy
WN
Chicago → Portland
14h 10m
5:25 AM - 12:15 PM • 1 stop
WN
Chicago → Portland
9h 10m
2:10 PM - 10:00 PM • 1 stop
$826
Southwest Airlines
Jul 05 - Jul 11, Economy
DL
Chicago → Portland
15h 43m
9:54 AM - 5:37 PM • 1 stop
DL
Chicago → Portland
15h 52m
6:15 AM - 5:52 PM • 1 stop
$1235
Delta 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 5:15 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 552
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 1:4900 pm

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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