
Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago O'Hare International Airport (ORD)
- Delta
Delta
- American Airlines
American Airlines
- United
United
- JetBlue Airways
JetBlue Airways
- Southwest Airlines
Southwest Airlines
- Plan, book, fly with confidence
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Cheap flights from Portland (PWM) to Chicago (ORD)
Prices were available within the past 7 days and start at CA $140 for one-way flights and CA $289 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from Portland (PWM) to Chicago (ORD)
August is typically the cheapest month to fly
Graph displaying average flight prices per month
Origin airport | Portland Intl. Jetport |
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, JetBlue Airways, United |
Roundtrip price | CA $288 |
Distance | 1435 km |
Average flight time | 1 hour 57 mins |
Portland to Chicago Flights
The easy way to book your flights from Portland to Chicago
With Expedia, it’s simple to find and book flights to Chicago from Portland whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are American Airlines, Qatar Airways, Air New Zealand, United Airlines nonstop flights to O'Hare Intl., too.
Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Portland to Chicago today, tomorrow, or this week.
Save dollars with cheap flights from Portland Intl. Jetport, PWM to O'Hare Intl., ORD
Sort your search results by price to find great deals on your flight from Portland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Portland currently is just CA $289 rising to CA $440.
Here are more money-saving tips:
- Fly in September when flight prices are normally at their lowest
- Book about a month to 6 weeks before you travel for the best prices to Chicago
- Avoid peak season and weekends when flights can cost more
- Early morning and late-night flights are sometimes cheaper, so try varying your travel times
- One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!
Reasons to choose Expedia for your flight to Chicago from Portland
Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.
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Top Routes from Portland
- Portland to Phoenix (PWM - PHX)
- Portland to Miami (PWM - MIA)
- Portland to Fort Lauderdale (PWM - FLL)
- Portland to Orange County (PWM - SNA)
- Portland to Halifax (PWM - YHZ)
- Portland to Victoria (PWM - YYJ)
- Portland to Seattle (PWM - SEA)
- Portland to New York (PWM - JFK)
- Portland to Vancouver (PWM - YVR)
- Portland to Providenciales (PWM - PLS)
- Portland to Orlando (PWM - MCO)
- Portland to Cancun (PWM - CUN)
Top Routes to Chicago
- Ottawa to Chicago (YOW - ORD)
- Calgary to Chicago (YYC - ORD)
- Kelowna to Chicago (YLW - ORD)
- Detroit to Chicago (DTW - ORD)
- Saskatoon to Chicago (YXE - ORD)
- Winnipeg to Chicago (YWG - ORD)
- Halifax to Chicago (YHZ - ORD)
- Québec to Chicago (YQB - ORD)
- Victoria to Chicago (YYJ - ORD)
- Seattle to Chicago (SEA - ORD)
- Montreal to Chicago (YUL - ORD)
- Buffalo to Chicago (BUF - ORD)
Top Routes from Portland
Top Routes to Chicago
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