Cheap Flight Tickets from Chicago (MDW) to Portland (PDX), Starting at $195

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

$327

DL Delta Airlines • 1 stop • 9h 15m

Aug 10 – Aug 17

The cheapest round trip flight from Chicago to Portland (MDW-PDX-MDW) is currently $327

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Cheapest Direct Flight

$195

WN Southwest Airlines • nonstop • 6h 55m

Sep 22

The cheapest nonstop flight from Chicago to Portland (MDW-PDX) is currently $195

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Fastest Flight

6h 50m

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

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.

Aug 10 - Aug 17, Economy
DL
Chicago → Portland
9h 15m
7:25 PM - 11:20 PM • 1 stop
DL
Chicago → Portland
15h 4m
10:55 PM - 9:59 AM • 1 stop
$327
Delta Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → Portland
6h 55m
8:50 PM - 11:05 PM • nonstop
WN
Chicago → Portland
6h 40m
11:35 AM - 5:35 PM • nonstop
$483
Southwest Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → Portland
13h 20m
9:00 AM - 3:00 PM • 1 stop
WN
Chicago → Portland
5h 55m
6:15 AM - 12:10 PM • nonstop
$488
Southwest Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → Portland
15h 50m
11:10 AM - 7:00 PM • 1 stop
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$493
Southwest Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → Portland
10h 50m
4:25 PM - 9:15 PM • 1 stop
WN
Chicago → Portland
6h 40m
11:35 AM - 5:35 PM • nonstop
$493
Southwest Airlines
Aug 10 - Aug 17, Economy
WN
Chicago → Portland
13h 40m
10:15 AM - 4:35 PM • 1 stop
WN
Chicago → Portland
5h 55m
11:30 PM - 5:25 AM • nonstop
$493
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 9:00 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 483
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 8:55 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to pdx?
You can find budget-friendly flights from Chicago Midway International Airport (mdw) to Portland International Airport (pdx) on Southwest Airlines. As you're booking in advance, with 36 days prior to your trip, it's likely that you'll secure a low fare. Consider flying during the off-season for even cheaper airfares.
What's the popular airline to fly from mdw to pdx?
Southwest Airlines offers flights from Chicago Midway International Airport (mdw) to Portland International Airport (pdx). As a one-way trip with no stops, you can expect a budget-friendly flight. Booking in advance is recommended as Southwest Airlines often provides low fares for early bookings. You can find the cheapest airfares on their official website or through FareLeaders.com.
What's the cheapest day of the week to fly from mdw to pdx?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Portland International Airport (pdx) is Sunday. You can find budget-friendly flights on this day to save on airfares.
What's the cheapest month to fly from mdw to pdx?
The cheapest month to fly from Chicago Midway International Airport (mdw) to Portland International Airport (pdx) is November. This is based on historical data, which suggests that airfares tend to be lower during this time of year. You can expect to find budget-friendly flights with low fares during this period.
Which airline/airlines fly from mdw to pdx?
The airlines that fly from Chicago Midway International Airport (mdw) to Portland International Airport (pdx) include Allegiant (G4), Frontier Airlines (F9), Delta Airlines (DL), Southwest Airlines (WN), Aeromexico (AM), United Airlines (UA), American Airlines (AA), Air New Zealand (NZ), Volaris Airline (Y4), and Austrian Airlines (OS). You can find the cheapest flights on our website for your upcoming one-way trip.
What is the cheapest airline to fly from Chicago Midway International Airport (mdw) to Portland International Airport (pdx)?
Southwest Airlines (WN)
Can I find affordable airfare options on cheapflights for my July trip?
Yes, you can find affordable airfare options on cheapflights.com
What does it mean when a flight is described as 'muy' convenient for your travel plans?
It means the flight offers flexible scheduling and minimal waiting times.
How can I ensure my web-based travel agency provides the best airfare options for my trip?
You can compare prices across multiple airlines and book in advance to secure better deals.
What are some popular airlines that operate direct flights from Milwaukee to Portland International Airport (pdx)?
Allegiant, Frontier Airlines, Delta Airlines, Southwest Airlines

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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