￥18,230 Cheap Flights from Portland (PDX) to Chicago (ORD)

View ￥18,230 flight on Sat, Sep 27, 2025Opens in a new window

Popular airlines from Portland International Airport (PDX) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Portland to Chicago (PDX-ORD)

Prices were available within the past 7 days and start at ￥18,230 for one-way flights and ￥39,570 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥39,570 Roundtrip, just found
￥39,570
Roundtrip
just found
Select Delta flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥39,570 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥39,700 Roundtrip, just found
￥39,700
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥39,700 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥43,140 Roundtrip, just found
￥43,140
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥43,140 just found
United
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥43,470 Roundtrip, just found
￥43,470
Roundtrip
just found
Select United flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥43,470 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥44,580 Roundtrip, just found
￥44,580
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥44,580 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥44,800 Roundtrip, just found
￥44,800
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥44,800 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥46,150 Roundtrip, just found
￥46,150
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥46,150 just found
Delta
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥46,230 Roundtrip, just found
￥46,230
Roundtrip
just found
Select Delta flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥46,230 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥46,260 Roundtrip, just found
￥46,260
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥46,260 just found
American Airlines
Thu, Sep 18 - Fri, Sep 19
PDX
Portland
ORD
Chicago
￥47,590 Roundtrip, just found
￥47,590
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Portland to Chicago, returning Fri, Sep 19, priced at ￥47,590 just found

Find the cheapest month to fly from Portland (PDX) to Chicago (ORD)

August is typically the cheapest month to fly

From ￥14,776 - ￥28,993 per traveler.

Graph displaying average flight prices per month

Flights from Portland (PDX) to Chicago (ORD)
Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Roundtrip price
￥39,570
Distance
2774 km
Average flight time
6 hours 5 mins

Portland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Portland to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with PDX to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Portland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from PDX to O'Hare Airport?
Round-trip journeys between PDX Airport and O'Hare Intl. Airport (ORD) start from ￥39,570. This is based on fares quoted within the last 7 days on Expedia for flights departing within the next year — book now so you don't miss out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from PDX to O'Hare Airport?
This varies between air carriers, as each one has its own set of terms and conditions. Head to the Customer Service Portal, where there are easy-to-follow instructions on how to cancel online.
How do I find cheap flights from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Portland Airport to ORD flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from PDX to O'Hare Intl. Airport (ORD)?
The average flight time between Portland Intl. Airport (PDX) and O'Hare Intl. Airport (ORD) is 4 hours and 3 minutes. If you get peckish on longer flights, pack a few healthy snacks in your carry-on baggage.
How far is the flight from Portland Intl. Airport (PDX) to O'Hare Airport?
Expect to be up above the clouds for a while, as the flight distance from Portland Airport to ORD is 2,800 kilometers. Put together a playlist of your favorite songs before you leave home to keep yourself entertained during your trip.
Which airlines fly direct from Portland Airport to O'Hare Airport?
A popular airline that operates on the route from Portland Intl. Airport (PDX) to ORD is United Airlines (UA). It offers 126 flights a month. Alaska Airlines (AS) is also worth checking out. It operates 60 flights each month. Between these two airlines, you'll be able to find a great deal from Portland to Chicago.
Are Portland Intl. Airport (PDX) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices change all the time, so not always. While last-minute deals between PDX Airport and O'Hare Airport are possible, it's also a good idea to keep track of prices well before you fly. In fact, some airlines announce their prices up to 12 months prior to the departure date. Expedia is constantly updating the biggest bargains around, so check back often and be ready to lock in your seat when fare prices drop.

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