Cheap Flight Tickets from Portland (PWM) to Chicago (ORD), Starting at $280

Good to Know: Cheapest and Fastest PWM - ORD Flights

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

Cheapest Round Trip Flight

$280

UA United Airlines • 1 stop • 6h 47m

Jul 23 – Aug 13

The cheapest round trip flight from Portland to Chicago (PWM-ORD-PWM) is currently $280

🔍 Search Flights

Cheapest Direct Flight

$387

UA United Airlines • nonstop • 5h

Jul 23

The cheapest nonstop flight from Portland to Chicago (PWM-ORD) is currently $387

🔍 Search Flights

Fastest Flight

5h

The fastest nonstop flight from Portland to Chicago (PWM-ORD) takes 5h

Latest Flight Deals from Portland (PWM) to Chicago (ORD)

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

Jul 23 - Aug 13, Economy
UA
Portland → Chicago
6h 47m
5:15 AM - 11:53 AM • 1 stop
UA
Portland → Chicago
5h 28m
6:00 AM - 1:55 PM • 1 stop
$280
United Airlines
Jul 23 - Aug 13, Economy
AA
Portland → Chicago
7h 23m
2:56 PM - 7:26 PM • 1 stop
AA
Portland → Chicago
5h 42m
5:55 PM - 11:59 PM • 1 stop
$315
American Airlines
Jul 23 - Aug 13, Economy
AA
Portland → Chicago
8h 51m
6:59 PM - 11:30 PM • 1 stop
AA
Portland → Chicago
8h 24m
5:55 PM - 11:59 PM • 1 stop
$454
American Airlines
Jul 23 - Aug 13, Economy
AA
Portland → Chicago
10h 48m
5:45 AM - 11:33 AM • 1 stop
AA
Portland → Chicago
8h 24m
5:55 PM - 11:59 PM • 1 stop
$454
American Airlines
Jul 23 - Aug 13, Economy
AA
Portland → Chicago
10h 26m
2:25 PM - 7:51 PM • 1 stop
AA
Portland → Chicago
8h 24m
5:55 PM - 11:59 PM • 1 stop
$486
American Airlines
Jul 23 - Aug 13, Economy
AA
Portland → Chicago
8h 29m
8:00 AM - 12:09 PM • 1 stop
AA
Portland → Chicago
8h 24m
5:55 PM - 11:59 PM • 1 stop
$486
American 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?
PWM
What’s the most popular airline flying from PWM to ORD?
The most popular airline flying from Portland to Chicago are
Can I fly from PWM to ORD non-stop?
Yes, you can fly PWM 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 PWM to ORD Airport?
The earliest flight leaves PWM at 5:15 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 PWM 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 2 hour to fly non-stop from PWM to ORD, which is 899.87 miles by air.
Which airlines provide the cheapest flights from Portland (PWM) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from PWM were found on AA : USD 486
Do I need a passport to fly between PWM and ORD?
No
What’s the latest departure time from PWM to ORD ?
The last flight leaves PWM at 7:39 pm

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

Origin Airport Portland International Jetport , Portland, US
Destination Airport Chicago O'Hare International , Chicago, US
Distance 900 miles

More Flight Options for Portland (PWM) and Chicago (ORD)

Why Fareleaders for PWM to ORD Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Portland to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on PWM to ORD flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Portland to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Portland (PWM) to Chicago (ORD)
Terms and Conditions*