
Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)
- JetBlue Airways
JetBlue Airways
- American Airlines
American Airlines
- Delta
Delta
- United
United
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
- Sun Country Airlines
Sun Country Airlines
- Plan, book, fly with confidence
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Cheap flights from Chicago to Portland (ORD-PWM)
Prices were available within the past 7 days and start at €89 for one-way flights and €246 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€246 Return, found 5 days ago
€246
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€255 Return, found 5 days ago
€255
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€257 Return, found 5 days ago
€257
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€266 Return, found 5 days ago
€266
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€268 Return, found 5 days ago
€268
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€276 Return, found 5 days ago
€276
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€278 Return, found 5 days ago
€278
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€285 Return, found 5 days ago
€285
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€495 Return, found 5 days ago
€495
Return
found 5 days ago

Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
PWM
Portland
€699 Return, found 5 days ago
€699
Return
found 5 days ago
Find the cheapest month to fly from Chicago (ORD) to Portland (PWM)
September is typically the cheapest month to fly
From €117 - €255 per traveller.
Graph displaying average flight prices per month
Origin airport | O'Hare Intl. |
Destination airport | Portland Intl. Jetport |
Return price | €246 |
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 €89 and roundtrip prices from €246. 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.
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Top Routes from Chicago
- Chicago to Newark Liberty Intl. Airport (ORD - EWR)
- Chicago to Belgrade (ORD - BEG)
- Chicago to New York (ORD - LGA)
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- Chicago to New York (ORD - JFK)
- Chicago to Dublin (ORD - DUB)
- Chicago to Nashville (ORD - BNA)
- Chicago to Athens (ORD - ATH)
- Chicago to Green Bay (ORD - GRB)
- Chicago to London (ORD - LHR)
- Chicago to Atlanta (ORD - ATL)
Top Routes to Portland
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Flights
- Flights from New York (JFK) to Chicago (ORD)
- Flights from Chicago (ORD) to Shannon (SNN)
- Flights from Boston (BOS) to Chicago (ORD)
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Shannon (SNN) to Chicago (ORD)
- Flights from Chicago (ORD) to Los Angeles (LAX)
- Flights from Chicago (ORD) to San Diego (SAN)
- Flights from Dublin (DUB) to Chicago (ORD)
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- Flights from Naples (NAP) to Chicago (ORD)
- Flights from London (LHR) to Chicago (ORD)
- Flights from Chicago (ORD) to Las Vegas (LAS)
- Flights from Chicago (ORD) to Dublin (DUB)
- Flights from Chicago (ORD) to St. Louis (STL)
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- Flights from Chicago (ORD) to Boston (BOS)
- Flights from Chicago (ORD) to Minneapolis - St. Paul (MSP)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Chicago (ORD) to Miami (MIA)
- Flights from Orlando (MCO) to Chicago (ORD)
- Flights from Chicago (ORD) to Nashville (BNA)
- Flights from Chicago (ORD) to Seattle (SEA)
- Flights from Cork (ORK) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Chicago (ORD) to Indianapolis (IND)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Chicago (ORD) to New York (LGA)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Chicago (ORD) to Detroit (DTW)
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