Cheap Flight Tickets from Portland (PDX) to Chicago (ORD), Starting at $256

Good to Know: Cheapest and Fastest PDX - ORD Flights

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

Cheapest Round Trip Flight

$278

AS Alaska Airlines • nonstop • 6h 41m

Jul 12 – Jul 19

The cheapest round trip flight from Portland to Chicago (PDX-ORD-PDX) is currently $278

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Cheapest One way Flight

$390

AA American Airlines • 1 stop • 11h 52m

Jun 25

The cheapest one way flight from Portland to Chicago (PDX-ORD) is currently $390

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Cheapest Direct Flight

$714

UA United Airlines • nonstop • 6h 53m

Jul 12

The cheapest nonstop flight from Portland to Chicago (PDX-ORD) is currently $714

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Fastest Flight

5h 59m

The fastest nonstop flight from Portland to Chicago (PDX-ORD) takes 5h 59m

Top Airlines Flying from Portland to Chicago

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 (ORD)

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

Jul 12 - Jul 19, Economy
AS
Portland → Chicago
6h 41m
10:59 PM - 5:00 AM • nonstop
AS
Portland → Chicago
12h 1m
6:00 AM - 11:21 AM • 1 stop
$278
Alaska Airlines
Jul 12 - Jul 19, Economy
AS
Portland → Chicago
10h 50m
9:30 PM - 6:20 AM • 1 stop
AS
Portland → Chicago
7h 5m
7:20 AM - 9:45 AM • nonstop
$278
Alaska Airlines
Jul 12 - Jul 19, Economy
AS
Portland → Chicago
15h 2m
8:19 AM - 7:21 PM • 1 stop
AS
Portland → Chicago
7h 5m
7:20 AM - 9:45 AM • nonstop
$278
Alaska Airlines
Jul 12 - Jul 19, Economy
F9
Portland → Chicago
17h 21m
5:36 PM - 6:17 AM • 1 stop
F9
Portland → Chicago
20h 49m
7:15 AM - 6:04 PM • 1 stop
$642
Frontier Airlines
Jul 12 - Jul 19, Economy
UA
Portland → Chicago
6h 53m
2:25 PM - 8:38 PM • nonstop
UA
Portland → Chicago
7h 7m
1:30 PM - 3:57 PM • nonstop
$714
United Airlines
Jul 12 - Jul 19, Economy
UA
Portland → Chicago
6h 54m
10:46 AM - 5:00 PM • nonstop
UA
Portland → Chicago
7h 7m
1:30 PM - 3:57 PM • nonstop
$714
United 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 ORD?
The most popular airline flying from Portland to Chicago are
Can I fly from PDX to ORD non-stop?
Yes, you can fly PDX to ORD 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 ORD Airport?
The earliest flight leaves PDX at 5:00 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
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 ORD?
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 ORD, which is 1739.26 miles by air.
Which airlines provide the cheapest flights from Portland (PDX) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from PDX were found on AS : USD 836
Do I need a passport to fly between PDX and ORD?
No
What’s the latest departure time from PDX to ORD ?
The last flight leaves PDX at 11:40 pm

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

Origin Airport Portland International , Portland, US
Destination Airport Chicago O'Hare International , Chicago, US
Distance 1739 miles

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