
Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago O'Hare Intl. Airport (ORD)
- Delta
Delta
- American Airlines
American Airlines
- United
United
- JetBlue Airways
JetBlue Airways
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
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Cheap flights from Portland to Chicago (PWM-ORD)
Prices were available within the past 7 days and start at €111 for one-way flights and €192 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€192 Return, found 5 days ago
€192
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€232 Return, found 5 days ago
€232
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€236 Return, found 5 days ago
€236
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€236 Return, found 5 days ago
€236
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€240 Return, found 5 days ago
€240
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€250 Return, found 5 days ago
€250
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€253 Return, found 5 days ago
€253
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€253 Return, found 5 days ago
€253
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€257 Return, found 5 days ago
€257
Return
found 5 days ago

Sat, 30 Aug - Sun, 31 Aug
PWM
Portland
ORD
Chicago
€270 Return, found 5 days ago
€270
Return
found 5 days ago
Find the cheapest month to fly from Portland (PWM) to Chicago (ORD)
August is typically the cheapest month to fly
From €130 - €342 per traveller.
Graph displaying average flight prices per month
Origin airport | Portland Intl. Jetport |
Destination airport | O'Hare Intl. |
Return price | €191 |
Distance | 1435 km |
Average flight time | 1 hour 59 mins |
Perfect flights from Portland to Chicago
Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Portland to Chicago. 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 Chicago, 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 Portland Intl. Jetport to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from €111 and roundtrip prices from €192. 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 O'Hare Intl. and explore Chicago 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 PWM to ORD travel arrangements today and embark on the journey of a lifetime in Chicago.
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Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
- New York to Chicago (LGA - ORD)
- Cork to Chicago (ORK - ORD)
- Istanbul to Chicago (IST - ORD)
- Warsaw to Chicago (WAW - ORD)
- New York to Chicago (JFK - ORD)
- Dublin to Chicago (DUB - ORD)
- Budapest to Chicago (BUD - ORD)
- Shannon to Chicago (SNN - ORD)
- Vilnius to Chicago (VNO - ORD)
- London to Chicago (LHR - ORD)
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Expedia's Latest Trends
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)
- Flights from Chicago (ORD) to Dallas (DFW)
- 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)
- Flights from Philadelphia (PHL) to Chicago (ORD)
- 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)
- Flights from Chicago (ORD) to San Francisco (SFO)
*Available to Expedia members.