Cheap Flight Tickets from Chicago (MDW) to Portland (PDX), Starting at $183

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

$255

WN Southwest Airlines • 1 stop • 22h 35m

Nov 06 – Nov 08

The cheapest round trip flight from Chicago to Portland (MDW-PDX-MDW) is currently $255

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Cheapest Direct Flight

$183

WN Southwest Airlines • nonstop • 7h 20m

Nov 05

The cheapest nonstop flight from Chicago to Portland (MDW-PDX) is currently $183

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Fastest Flight

7h 20m

The fastest nonstop flight from Chicago to Portland (MDW-PDX) takes 7h 20m

Top Airlines Flying from Chicago to Portland

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska 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.

Nov 06 - Nov 08, Economy
WN
Chicago → Portland
22h 35m
9:15 PM - 9:10 AM • 1 stop
WN
Chicago → Portland
5h 45m
11:30 PM - 5:15 AM • nonstop
$255
Southwest Airlines
Nov 06 - Nov 08, Economy
WN
Chicago → Portland
22h 30m
10:00 AM - 9:50 PM • 1 stop
WN
Chicago → Portland
5h 45m
11:30 PM - 5:15 AM • nonstop
$255
Southwest Airlines
Nov 06 - Nov 08, Economy
WN
Chicago → Portland
19h
10:40 AM - 8:20 PM • 1 stop
WN
Chicago → Portland
26h 45m
5:30 PM - 11:35 AM • 1 stop
$259
Southwest Airlines
Nov 06 - Nov 08, Economy
WN
Chicago → Portland
22h 5m
8:55 AM - 8:20 PM • 1 stop
WN
Chicago → Portland
26h 45m
5:30 PM - 11:35 AM • 1 stop
$259
Southwest Airlines
Nov 06 - Nov 08, Economy
WN
Chicago → Portland
16h 50m
2:35 PM - 10:45 PM • 1 stop
WN
Chicago → Portland
26h 45m
5:30 PM - 11:35 AM • 1 stop
$259
Southwest Airlines
Nov 06 - Nov 08, Economy
DL
Chicago → Portland
40h 44m
1:27 PM - 12:11 PM • 2 stops
DL
Chicago → Portland
33h 25m
7:59 PM - 6:04 PM • 2 stops
$262
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 8:55 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 DL : USD 262
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 9:15 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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