Cheap Flight Tickets from Portland (PDX) to Chicago (CHI), Starting at $307

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

$307

DL Delta Airlines • 1 stop •

Jun 26 – Jul 02

The cheapest round trip flight from Portland to Chicago (PDX-CHI-PDX) is currently $307

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Cheapest Direct Flight

$345

UA United Airlines • nonstop •

Jun 26

The cheapest nonstop flight from Portland to Chicago (PDX-CHI) is currently $345

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Fastest Flight

6h 41m

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

Top Airlines Flying from Portland to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Sun Country Airlines (SY)

Sun Country Airlines

WestJet Airlines

WestJet 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.

Jun 26 - Jul 02, Economy
DL
Portland → Chicago
- • 1 stop
DL
Portland → Chicago
- • 1 stop
$307
Delta Airlines
Jun 26 - Jul 02, Economy
UA
Portland → Chicago
6h 53m
2:25 PM - 8:38 PM • nonstop
AS
Portland → Chicago
7h 15m
2:12 PM - 4:47 PM • nonstop
$509
United Airlines
Jun 26 - Jul 02, Economy
F9
Portland → Chicago
10h 17m
12:26 PM - 8:43 PM • 1 stop
F9
Portland → Chicago
35h 9m
7:20 AM - 5:24 PM • 1 stop
$529
Frontier Airlines
Jun 26 - Jul 02, Economy
AA
Portland → Chicago
6h 41m
10:59 PM - 5:00 AM • nonstop
AS
Portland → Chicago
7h 15m
2:12 PM - 4:47 PM • nonstop
$553
American Airlines
Jun 26 - Jul 02, Economy
AS
Portland → Chicago
6h 41m
10:59 PM - 5:00 AM • nonstop
AV
Portland → Chicago
78h 59m
11:20 PM - 8:59 PM • 3 stops
$1130
Alaska Airlines
Jun 26 - Jul 02, Economy
UA
Portland → Chicago
22h 27m
1:14 PM - 5:01 AM • 1 stop
UA
Portland → Chicago
10h 19m
10:54 AM - 3:13 PM • 1 stop
$1575
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 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 7:00 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 F9 : USD 529
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 11:4000 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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