
Popular airlines from Portland International Airport (PDX) to Chicago O'Hare Intl. Airport (ORD)
- Alaska Airlines
Alaska Airlines
- United
United
- Delta
Delta
- American Airlines
American Airlines
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
- Sun Country Airlines
Sun Country Airlines
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 15% on select hotels after you book a flight*
Cheap flights from Portland to Chicago (PDX-ORD)
Prices were available within the past 7 days and start at €87 for one-way flights and €172 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, 8 Jan - Wed, 14 Jan
PDX
Portland
ORD
Chicago
€172 Return, found 2 days ago
€172
Return
found 2 days ago

Thu, 8 Jan - Wed, 14 Jan
PDX
Portland
ORD
Chicago
€180 Return, found 2 days ago
€180
Return
found 2 days ago

Sat, 10 Jan - Sat, 17 Jan
PDX
Portland
ORD
Chicago
€187 Return, found 5 days ago
€187
Return
found 5 days ago

Thu, 1 Jan - Wed, 7 Jan
PDX
Portland
ORD
Chicago
€196 Return, found 4 days ago
€196
Return
found 4 days ago

Thu, 8 Jan - Wed, 14 Jan
PDX
Portland
ORD
Chicago
€203 Return, found 2 days ago
€203
Return
found 2 days ago

Thu, 1 Jan - Wed, 7 Jan
PDX
Portland
ORD
Chicago
€205 Return, found 4 days ago
€205
Return
found 4 days ago

Thu, 15 Jan - Wed, 21 Jan
PDX
Portland
ORD
Chicago
€205 Return, found 1 day ago
€205
Return
found 1 day ago

Thu, 8 Jan - Wed, 14 Jan
PDX
Portland
ORD
Chicago
€211 Return, found 2 days ago
€211
Return
found 2 days ago

Thu, 15 Jan - Wed, 21 Jan
PDX
Portland
ORD
Chicago
€214 Return, found 1 day ago
€214
Return
found 1 day ago

Thu, 8 Jan - Wed, 14 Jan
PDX
Portland
ORD
Chicago
€215 Return, found 2 days ago
€215
Return
found 2 days ago
Find the cheapest month to fly from Portland (PDX) to Chicago (ORD)
August is typically the cheapest month to fly
From €91 - €234 per traveller.
Origin airport | Portland Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, United |
Return price | €171 |
Distance | 2774 km |
Average flight time | 6 hours 44 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 , 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. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from €87 and roundtrip prices from €172. 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 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 Chicago.
Explore a world of travel with Expedia
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Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
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- Boston to Chicago (BOS - ORD)
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- 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)
- Tucson to Chicago (TUS - ORD)
- Vilnius to Chicago (VNO - 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.