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Cheap Flights from Portland (PDX) to Chicago (MDW)
Prices were available within the past 7 days and start at NZ$313 for one-way flights and NZ$1,105 for round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed., 22 May - Wed., 29 May
PDX
Portland
MDW
Chicago
NZ$1,105 Return, found 3 days ago
NZ$1,105
Return
found 3 days ago
Wed., 22 May - Wed., 29 May
PDX
Portland
MDW
Chicago
NZ$1,170 Return, found 3 days ago
NZ$1,170
Return
found 3 days ago
Thu., 23 May - Wed., 29 May
PDX
Portland
MDW
Chicago
NZ$1,449 Return, found 3 days ago
NZ$1,449
Return
found 3 days ago
Thu., 23 May - Wed., 29 May
PDX
Portland
MDW
Chicago
NZ$1,514 Return, found 3 days ago
NZ$1,514
Return
found 3 days ago
Origin airport | Portland Intl. |
Destination airport | Midway Intl. |
Return price | NZ$1,104 |
Distance | 2794 km |
Average flight time | 5 hours 55 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. to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares from NZ$313 and roundtrip prices from NZ$1,105. 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 Midway 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 PDX to MDW travel arrangements today and embark on the journey of a lifetime in Chicago.
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Top Routes from Portland
Top Routes to Chicago
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Chicago Flight Deals
Chicago
NZ$620.70
Alternative Routes
- McNary Field Airport (SLE)
- Astoria Regional Airport (AST)
- Corvallis Municipal Airport (CVO)
- Robert's Field Airport (RDM)
- Yakima Air Terminal - McAllister Field Airport (YKM)
- Seattle - Tacoma Intl. Airport (SEA)
- Boeing Field Airport (BFI)
- Lake Union Seaplane Base Airport (LKE)
- Seattle Paine Field Intl. Airport Airport (PAE)
- Richland Airport (RLD)
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