Cheap Flight Tickets from Portland (PDX) to Chicago (ORD), Starting at $158

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

$158

UA United Airlines • 1 stop • 10h 22m

Aug 28 – Aug 28

The cheapest round trip flight from Portland to Chicago (PDX-ORD-PDX) is currently $158

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Cheapest Direct Flight

$176

UA United Airlines • nonstop • 6h 53m

Aug 28

The cheapest nonstop flight from Portland to Chicago (PDX-ORD) is currently $176

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Fastest Flight

6h 41m

The fastest nonstop flight from Portland to Chicago (PDX-ORD) takes 6h 41m

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.

Aug 28 - Aug 28, Economy
UA
Portland → Chicago
10h 22m
7:00 AM - 4:36 PM • 1 stop
F9
Portland → Chicago
11h 44m
9:20 PM - 11:35 AM • 1 stop
$158
United Airlines
Aug 28 - Aug 29, Economy
UA
Portland → Chicago
13h 35m
11:15 AM - 9:30 PM • 1 stop
UA
Portland → Chicago
10h 10m
10:55 AM - 3:05 PM • 1 stop
$175
United Airlines
Aug 28 - Aug 29, Economy
AS
Portland → Chicago
17h 19m
5:41 PM - 6:20 AM • 1 stop
AS
Portland → Chicago
11h 41m
6:54 PM - 11:55 PM • 1 stop
$417
Alaska Airlines
Aug 28 - Aug 29, Economy
AS
Portland → Chicago
15h 26m
7:55 AM - 7:21 PM • 1 stop
AS
Portland → Chicago
7h 8m
2:22 PM - 4:50 PM • nonstop
$613
Alaska Airlines
Aug 27 - Aug 28, Economy
DL
Portland → Chicago
15h 18m
10:55 PM - 10:13 AM • 1 stop
DL
Portland → Chicago
10h
7:44 PM - 11:44 PM • 1 stop
$952
Delta Airlines
Aug 27 - Aug 28, Economy
UA
Portland → Chicago
14h 4m
7:15 PM - 5:59 AM • 1 stop
UA
Portland → Chicago
10h 10m
10:55 AM - 3:05 PM • 1 stop
$2211
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 5:59 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 UA : USD 2211
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 10:3500 am

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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