Cheap Flight Tickets from Portland (PDX) to Chicago (MDW), Starting at $246

Good to Know: Cheapest and Fastest PDX - MDW Flights

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

Cheapest Round Trip Flight

$565

WN Southwest Airlines • 1 stop • 12h 30m

Nov 01 – Nov 08

The cheapest round trip flight from Portland to Chicago (PDX-MDW-PDX) is currently $565

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Cheapest Direct Flight

$246

WN Southwest Airlines • nonstop • 5h 45m

Nov 02

The cheapest nonstop flight from Portland to Chicago (PDX-MDW) is currently $246

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Fastest Flight

5h 45m

The fastest nonstop flight from Portland to Chicago (PDX-MDW) takes 5h 45m

Top Airlines Flying from Portland to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Nov 01 - Nov 08, Economy
WN
Portland → Chicago
12h 30m
12:10 PM - 10:00 PM • 1 stop
WN
Portland → Chicago
7h 20m
9:15 PM - 11:55 PM • nonstop
$565
Southwest Airlines
Nov 01 - Nov 08, Economy
WN
Portland → Chicago
14h 5m
7:00 PM - 5:45 AM • 1 stop
WN
Portland → Chicago
19h 10m
9:55 PM - 7:45 AM • 1 stop
$566
Southwest Airlines
Nov 01 - Nov 08, Economy
WN
Portland → Chicago
12h 15m
8:10 PM - 5:45 AM • 1 stop
WN
Portland → Chicago
28h 45m
5:20 AM - 8:45 PM • 3 stops
$585
Southwest Airlines
Nov 01 - Nov 08, Economy
WN
Portland → Chicago
15h 45m
6:10 AM - 5:55 PM • 1 stop
WN
Portland → Chicago
28h 45m
5:20 AM - 8:45 PM • 3 stops
$585
Southwest Airlines
Nov 01 - Nov 08, Economy
WN
Portland → Chicago
13h 20m
7:35 AM - 5:35 PM • 2 stops
WN
Portland → Chicago
28h 45m
5:20 AM - 8:45 PM • 3 stops
$586
Southwest Airlines
Nov 01 - Nov 08, Economy
WN
Portland → Chicago
10h 30m
5:00 AM - 1:30 PM • 1 stop
WN
Portland → Chicago
7h 20m
9:15 PM - 11:55 PM • nonstop
$638
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?
PDX
What’s the most popular airline flying from PDX to MDW?
The most popular airline flying from Portland to Chicago are
Can I fly from PDX to MDW non-stop?
Yes, you can fly PDX 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 PDX to MDW Airport?
The earliest flight leaves PDX at 5:00 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 PDX 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 4 hour to fly non-stop from PDX to MDW, which is 1751.25 miles by air.
Which airlines provide the cheapest flights from Portland (PDX) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from PDX were found on WN : USD 585
Do I need a passport to fly between PDX and MDW?
No
What’s the latest departure time from PDX to MDW ?
The last flight leaves PDX at 11:30 pm

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

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

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