$100 Cheap Flights from Chicago (ORD) to Portland (PWM)

View $100 flight on Thu, Nov 27, 2025Opens 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 $100 for one-way flights and $183 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Sep 16 - Tue, Sep 30
ORD
Chicago
PWM
Portland
$183 Roundtrip, found 4 hours ago
$183
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Chicago to Portland, returning Tue, Sep 30, priced at $183 found 4 hours ago
United
Sun, Aug 31 - Fri, Sep 5
ORD
Chicago
PWM
Portland
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select United flight, departing Sun, Aug 31 from Chicago to Portland, returning Fri, Sep 5, priced at $192 found 2 days ago
JetBlue Airways
Fri, Sep 19 - Tue, Sep 30
ORD
Chicago
PWM
Portland
$198 Roundtrip, found 4 hours ago
$198
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Fri, Sep 19 from Chicago to Portland, returning Tue, Sep 30, priced at $198 found 4 hours ago
JetBlue Airways
Mon, Sep 15 - Tue, Sep 16
ORD
Chicago
PWM
Portland
$203 Roundtrip, found 4 hours ago
$203
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Mon, Sep 15 from Chicago to Portland, returning Tue, Sep 16, priced at $203 found 4 hours ago
JetBlue Airways
Sun, Sep 21 - Tue, Sep 30
ORD
Chicago
PWM
Portland
$210 Roundtrip, found 4 hours ago
$210
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sun, Sep 21 from Chicago to Portland, returning Tue, Sep 30, priced at $210 found 4 hours ago
Delta
Sun, Aug 31 - Fri, Sep 5
ORD
Chicago
PWM
Portland
$211 Roundtrip, found 2 days ago
$211
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Aug 31 from Chicago to Portland, returning Fri, Sep 5, priced at $211 found 2 days ago
JetBlue Airways
Fri, Sep 19 - Thu, Oct 2
ORD
Chicago
PWM
Portland
$213 Roundtrip, found 4 hours ago
$213
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Fri, Sep 19 from Chicago to Portland, returning Thu, Oct 2, priced at $213 found 4 hours ago
American Airlines
Sat, Aug 23 - Sat, Aug 30
ORD
Chicago
PWM
Portland
$215 Roundtrip, found 3 hours ago
$215
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Aug 23 from Chicago to Portland, returning Sat, Aug 30, priced at $215 found 3 hours ago
United
Fri, Oct 31 - Tue, Nov 4
ORD
Chicago
PWM
Portland
$215 Roundtrip, found 15 hours ago
$215
Roundtrip
found 15 hours ago
Select United flight, departing Fri, Oct 31 from Chicago to Portland, returning Tue, Nov 4, priced at $215 found 15 hours ago
Southwest Airlines
Sat, Aug 23 - Sat, Aug 30
ORD
Chicago
PWM
Portland
$226 Roundtrip, found 3 hours ago
$226
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Portland, returning Sat, Aug 30, priced at $226 found 3 hours ago

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

September is typically the cheapest month to fly

From $84 - $262 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to Portland (PWM)
Origin airport
O'Hare Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$182
Distance
897 mi
Average flight time
3 hours 33 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 September. 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 $100 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?
You can book cheap return tickets starting from $231 from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving ORD on July 29 2025 and touching down at PWM. The price was last updated on July 3 2025 and has not changed since.
What is the cheapest month to fly from ORD to PWM?
The cheapest flights from ORD to PWM are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 ORD to PWM?
With fares starting at $90 for a one-way journey from ORD to PWM, United is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 31 2025. Prices were last updated on July 3 2025 and have not changed since.
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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