€118 Cheap Flights Chicago to Portland (ORD-PWM)

View €118 flight on Sun, 31 Aug 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 €118 for one-way flights and €242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€242 Return, found 3 days ago
€242
Return
found 3 days ago
Select American Airlines flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €242 found 3 days ago
Delta
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€242 Return, found 3 days ago
€242
Return
found 3 days ago
Select Delta flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €242 found 3 days ago
Delta
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€262 Return, found 3 days ago
€262
Return
found 3 days ago
Select Delta flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €262 found 3 days ago
Delta
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€263 Return, found 3 days ago
€263
Return
found 3 days ago
Select Delta flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €263 found 3 days ago
United
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€272 Return, found 3 days ago
€272
Return
found 3 days ago
Select United flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €272 found 3 days ago
Delta
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€275 Return, found 3 days ago
€275
Return
found 3 days ago
Select Delta flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €275 found 3 days ago
American Airlines
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€284 Return, found 3 days ago
€284
Return
found 3 days ago
Select American Airlines flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €284 found 3 days ago
American Airlines
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€285 Return, found 3 days ago
€285
Return
found 3 days ago
Select American Airlines flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €285 found 3 days ago
United
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€285 Return, found 3 days ago
€285
Return
found 3 days ago
Select United flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €285 found 3 days ago
Delta
Mon, 2 Feb - Thu, 5 Feb
ORD
Chicago
PWM
Portland
€290 Return, found 3 days ago
€290
Return
found 3 days ago
Select Delta flight, departing Mon, 2 Feb from Chicago to Portland, returning Thu, 5 Feb, priced at €290 found 3 days ago

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

September is typically the cheapest month to fly

From €118 - €261 per traveller.

Graph displaying average flight prices per month

Chicago to Portland route information
Origin airport
O'Hare Intl.
Destination airport
Portland Intl. Jetport
Return price
€241
Distance
1435 km
Average flight time
3 hours 34 mins

Perfect flights from Chicago to Portland

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Portland. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible O'Hare Intl. to Portland Intl. Jetport ticket options cater to your travel preferences, with incredible one-way fares from €118 and roundtrip prices from €242. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Portland Intl. Jetport and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Portland.

Frequently asked questions

How much is a flight from ORD to PWM?
Start packing your suitcase, because round-trip journeys from O'Hare Intl. Airport (ORD) to PWM start from €242. That's based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book now to secure the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to Portland Intl. Jetport Airport (PWM)?
We understand that your situation can change unexpectedly, so we've made it as easy as possible for you to cancel your flight online. Just visit the Customer Service Portal and follow the instructions.
How do I find cheap flights from O'Hare Airport to Portland Intl. Jetport 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 ORD to Portland Intl. Jetport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Portland Intl. Jetport?
A flight distance of just 1,450 kilometres separates Chicago and Portland. Once you're in the air, you won't get a chance to do much more than read the magazine in your seat pocket.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport?
Many travellers like to fly with United Airlines (UA) from O'Hare Intl. Airport (ORD) to PWM. This popular airline offers 60 flights every month, so you can pick a flight time that's right for you. You could also take a look at ticket prices with American Airlines (AA). This carrier operates 8 flights every month between Chicago and Portland.
Are ORD to Portland Intl. Jetport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from ORD to PWM at the last minute could be your ticket to a cheap deal. However, it could end up costing a great deal more! If you'd rather not take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to a year in advance. If your preferred carrier hasn't released tickets yet, check back often as deals are updated on Expedia all the time.

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