Cheap Flight Tickets from Portland (PDX) to Chicago (CHI), Starting at $146

Good to Know: Cheapest and Fastest PDX - CHI Flights

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

Cheapest Round Trip Flight

$146

AS Alaska Airlines • nonstop • 5h 20m

Aug 28 – Aug 28

The cheapest round trip flight from Portland to Chicago (PDX-CHI-PDX) is currently $146

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Cheapest Direct Flight

$146

AS Alaska Airlines • nonstop • 5h 20m

Aug 28

The cheapest nonstop flight from Portland to Chicago (PDX-CHI) is currently $146

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Fastest Flight

4h 15m

The fastest nonstop flight from Portland to Chicago (PDX-CHI) takes 4h 15m

Top Airlines Flying from Portland to Chicago

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 Portland (PDX) to Chicago (CHI)

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

Aug 28 - Aug 28, Economy
AS
Portland → Chicago
5h 20m
7:06 AM - 1:26 PM • nonstop
WN
Portland → Chicago
8h 35m
8:50 PM - 11:05 PM • nonstop
$146
Alaska Airlines
Aug 27 - Aug 28, Economy
AS
Portland → Chicago
10h 56m
2:03 PM - 11:59 PM • 1 stop
AS
Portland → Chicago
8h 48m
2:22 PM - 4:50 PM • nonstop
$149
Alaska Airlines
Aug 27 - Aug 28, Economy
WN
Portland → Chicago
8h 45m
1:35 PM - 10:00 PM • 1 stop
WN
Portland → Chicago
20h
10:00 AM - 7:00 PM • 1 stop
$176
Southwest Airlines
Aug 27 - Aug 28, Economy
UA
Portland → Chicago
11h 51m
11:15 AM - 8:26 PM • 1 stop
UA
Portland → Chicago
10h 32m
5:00 AM - 9:32 AM • 1 stop
$498
United Airlines
Aug 27 - Aug 28, Economy
UA
Portland → Chicago
15h
11:15 AM - 10:15 PM • 1 stop
UA
Portland → Chicago
10h 32m
5:00 AM - 9:32 AM • 1 stop
$561
United Airlines
Aug 27 - Aug 28, Economy
DL
Portland → Chicago
10h 36m
11:20 PM - 7:56 AM • 1 stop
DL
Portland → Chicago
13h 46m
1:51 PM - 8:17 PM • 1 stop
$781
Delta 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 CHI?
The most popular airline flying from Portland to Chicago are
Can I fly from PDX to CHI non-stop?
Yes, you can fly PDX to CHI 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 CHI Airport?
The earliest flight leaves PDX at 5:15 am and lands in CHI - Chicago All Airport
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 CHI?
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 CHI, which is 1739.26 miles by air.
Which airlines provide the cheapest flights from Portland (PDX) to Chicago (CHI) ?
In the past couple of days, the cheapest tickets to CHI from PDX were found on AS : USD 149
Do I need a passport to fly between PDX and CHI?
No
What’s the latest departure time from PDX to CHI ?
The last flight leaves PDX at 11:0200 pm

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

Origin Airport Portland International , Portland, US
Destination Airport Chicago All Airport, Chicago, US
Distance 1739 miles

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