$101 Cheap Flights from Chicago (ORD) to Portland (PWM)

View $101 flight on Wed, Apr 1, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)

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Cheap Flights from Chicago to Portland (ORD-PWM)

Prices were available within the past 7 days and start at $101 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Mon, Oct 20 - Tue, Oct 21
ORD
Chicago
PWM
Portland
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Oct 20 from Chicago to Portland, returning Tue, Oct 21, priced at $197 found 6 days ago
JetBlue Airways
Wed, Oct 22 - Sat, Oct 25
ORD
Chicago
PWM
Portland
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Oct 22 from Chicago to Portland, returning Sat, Oct 25, priced at $232 found 1 day ago
JetBlue Airways
Mon, Apr 20 - Thu, Apr 23
ORD
Chicago
PWM
Portland
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Mon, Apr 20 from Chicago to Portland, returning Thu, Apr 23, priced at $237 found 22 hours ago
American Airlines
Wed, Nov 19 - Thu, Nov 27
ORD
Chicago
PWM
Portland
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 19 from Chicago to Portland, returning Thu, Nov 27, priced at $247 found 1 day ago
United
Tue, Oct 21 - Wed, Oct 22
ORD
Chicago
PWM
Portland
$247 Roundtrip, found 2 days ago
$247
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 21 from Chicago to Portland, returning Wed, Oct 22, priced at $247 found 2 days ago
JetBlue Airways
Mon, Oct 20 - Tue, Oct 21
ORD
Chicago
PWM
Portland
$248 Roundtrip, found 6 days ago
$248
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Oct 20 from Chicago to Portland, returning Tue, Oct 21, priced at $248 found 6 days ago
JetBlue Airways
Fri, Oct 24 - Sat, Oct 25
ORD
Chicago
PWM
Portland
$255 Roundtrip, found 4 days ago
$255
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Oct 24 from Chicago to Portland, returning Sat, Oct 25, priced at $255 found 4 days ago
JetBlue Airways
Tue, Oct 21 - Sat, Oct 25
ORD
Chicago
PWM
Portland
$258 Roundtrip, found 8 hours ago
$258
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Chicago to Portland, returning Sat, Oct 25, priced at $258 found 8 hours ago
Delta
Wed, Nov 19 - Thu, Nov 27
ORD
Chicago
PWM
Portland
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 19 from Chicago to Portland, returning Thu, Nov 27, priced at $261 found 1 day ago
Southwest Airlines
Thu, Dec 4 - Tue, Dec 9
ORD
Chicago
PWM
Portland
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Tue, Dec 9, priced at $285 found 1 day ago

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

September is typically the cheapest month to fly

From $135 - $244 per traveler.

Alternative airports near Portland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Portland Intl. Jetport PWM. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $511
PWM
Portland Intl. Jetport
CheapestClosest
Average driving time to city center8 min
Flights from $511
Flights from Chicago (ORD) to Portland (PWM)
Origin airport
O'Hare Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$196
Distance
897 mi
Average flight time
3 hours 32 mins

Chicago to Portland Flights

The cheapest times to fly from Chicago to Portland

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Portland are during the month of October. You can find some of the cheapest flights from Chicago to Portland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Portland

Sunday is one of the best days to book for cheap flights from Chicago to Portland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Portland

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $101 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Portland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Portland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) cost?
Get a cheap one-way flight from $101 or cheap return flight from $197 from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
Traveling in October is a great way to save, as it's the cheapest month for flights between ORD and PWM. You'll often find the lowest prices during off-peak months.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
When flying out of O'Hare Intl. Airport (ORD), you can take a nonstop flight to Portland Intl. Jetport Airport (PWM) with United Airlines.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest ORD to PWM flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
On average, there is just 1 direct flight taking off from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) per day. If this doesn't fit your travel plans, check out flights with a layover. Just customize your search results on Expedia to include one or two stops to discover a better alternative.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
The 11 AM departures from ORD to PWM see the highest demand. Greater demand means you'll likely pay more for these departures. If you want to save money, book during off-peak hours.
What day of the week has the most flights from ORD to PWM?
Sunday has the most flights from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM). Consider jetting off on this day and you'll have a greater chance of finding a departure that fits your itinerary.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
O'Hare Intl. Airport (ORD)'s earliest flight to Portland Intl. Jetport Airport (PWM) departs at approximately 11:10AM UTC-6. With a flight time of 2h 32m, you'll touch down at around 2:42PM UTC-5.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
The average flight time from ORD to PWM is 2 hours and 32 minutes, covering a total distance of 900 mi.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) route, travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Portland from O'Hare Intl. Airport (ORD)?
Explore your flight options from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM). This is the only Portland airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) last-minute?
Last-minute fares from ORD to PWM are generally more expensive. To lock in the lowest rates, start searching for flights as soon as possible. That said, if you can play around with your travel dates, it's possible to land a cheap fare right before you leave.
Is it cheaper to book an ORD to PWM flight and hotel package?
Opting for an ORD to PWM flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our impressive range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
It's generally possible to reschedule or cancel your ORD to PWM flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.